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Full Ocean Views w/Private Beach on Siesta Key, Heated Pool Siesta Key, Florida

Full Ocean Views w/Private Beach on Siesta Key, Heated Pool

Located in Siesta Key, Florida, United States. Full Ocean Views w/Private Beach on Siesta Key, Heated Pool This beautiful 15th floor, 2 bedroom 2 bathroom condo offers full ocean and beach views throughout and is just steps from its private beach Siesta Key Beach in Siesta Key! This condo is almost 1200 sq. ft. being 1/4 of the entire 15th floor is located right on Siesta Key Beach, #1 rated beach in the USA with gulf views, bay views, city light views, Big Pass Lido Key Beach views. The Terrace has a gorgeous heated pool overlooking the ocean, game room & fitness center, community room, and your own numbered covered parking space, just steps to Siesta Key Village with plenty of dinging and shops.Terrace on the Beach Highlights:Corner Unit Condo Facing W/NW for Full Ocean Views ThroughoutStacked Sliders Open Wide to Open-Air Balconies (no screens!)Ocean Views from Bedrooms, Living & Dining RoomsKing Ensuite Master, Balcony w/Ocean Views, Cable Flat Screen TVGuest Ensuite Bedroom with 2 Twin Beds, Balcony w/ Ocean Views (no TV)alle

🛏 2 beds · 👥 4 guests
$192 /night
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Private house, Heated Pool, Pet friendly-walk to beach Siesta Key, Florida

Private house, Heated Pool, Pet friendly-walk to beach

Located in Siesta Key, Florida, United States. Private house, Heated Pool, Pet friendly-walk to beach Come and enjoy this pet friendly private house with your very own secluded heated swimming pool, in beautiful Siesta Key. Our Siesta Key Tropical Pool Paradise home is a 5 Min walk to the #1 Rated Beach with the best white sands you have ever seen. 10 Min walk to the village where you will find great local restaurants, your choice of ice cream shops, live music, village grocery store and liquor store - you won't need to head to the main land. Our renovated house offers you a home away from home with a full kitchen at your disposal if you choose to eat in. Our in ground heated pool is surrounded by a lush tropical oasis. We have completely renovated our house and are so happy to share our new and improved vacation home with you. This is the place you'll want visit, and return year after year. Check in times is 4 PM and check out time is 10 AM.*** Please Check out our other listing #1085215, also on Siesta Key, just two streets a

🛏 3 beds · 👥 6 guests
$194 /night
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Lovely Rental in Siesta Key Village! Walk to Beach Siesta Key, Florida

Lovely Rental in Siesta Key Village! Walk to Beach

Located in Siesta Key, Florida, United States. Lovely Rental in Siesta Key Village! Walk to Beach This lovely updated condo lies in the heart of Siesta Key Village!! Perfect Location!! Adorable condo updated, light & bright is now available and ready for you. Minorga Complex in Siesta Key Village includes a community heated pool with only an 8 minute walk to the beach! Your choice of cafe's, restaurants, shops and nightlight are all only steps away from the end unit condo. Walk to a local's favorite, The Salty Dog, for a grouper sandwich and an ice cold beer, or Solorzano's Pizza, another fave only a 3 minute walk and the Beach Club Nightclub has live entertainment along with pool tables.....all just around the corner. Only an 8 minute walk to sink your toes in the white famous powdery sands of the Gulf of Mexico where you can lie under an umbrella and relax with a good book and cold drink! (walk to your choice of Public beach accesses) #3 and #5 are just 0.4 miles (8 minute walk) and #2 & #4 are just 0.5 miles (9 minute wa

🛏 2 beds · 👥 6 guests
$188 /night
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Siesta Key Village - Townhouse - Heated Pool - Beach Walkable! Siesta Key, Florida

Siesta Key Village - Townhouse - Heated Pool - Beach Walkable!

Located in Siesta Key, Florida, United States. Siesta Key Village - Townhouse - Heated Pool - Beach Walkable! Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.This two-story townhouse style location, Siesta Key Dream’s closest unit to the Village, includes 3 spacious bedrooms that are perfect for up to 10 guests. On the first floor, you’ll experience an open floor plan connecting a welcoming living room, a dining room that seats 6, and kitchen featuring stainless steel appliances. On the second floor, you’ll find three bedrooms and two bathrooms. The main bedroom has an in-room bathroom, tub with jets, and a walk

🛏 3 beds · 👥 10 guests
$385 /night
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Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach Siesta Key, Florida

Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach

Located in Siesta Key, Florida, United States. Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach Welcome to Siesta Soul, a captivating retreat located just steps from the vibrant Siesta Key Village. This enchanting vacation home offers an ideal location and a backyard oasis, providing the perfect blend of convenience and relaxation for your Siesta Key getaway.Siesta Soul features four bedrooms and three full baths, including a master bedroom for added privacy and luxury. The master bedroom is a tranquil retreat with a comfortable king bed, providing a peaceful sanctuary for restful nights. The remaining three bedrooms offer queen beds, ensuring a comfortable night's sleep for everyone. Linens are provided for all beds, allowing you to simply relax and unwind upon your arrival.On the main level, you will greeted by a spacious living room and open kitchen that seamlessly connect together, creating the perfect space for entertaining and gathering with loved ones. The open floor plan e

🛏 4 beds · 👥 8 guests
$404 /night
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Cabana Cottage Across street from Beach  and  Heated Pool Siesta Key, Florida

Cabana Cottage Across street from Beach and Heated Pool

Located in Siesta Key, Florida, United States. Cabana Cottage Across street from Beach and Heated Pool The Cabana is small but mighty! A fully equipped kitchen complete with granite countertops, and a breakfast bar, with all of the comforts of home.The master bedroom has a King size Serta ICOMFORT Memory Foam Gel bed with a flat screen TV, and an attached European Rain shower bath. The second bedroom is two, twin Serta ICOMFORT Memory Foam Gel beds with a flat screen TV. The second tub/shower bathroom is off the kitchen area. Living room and dining areas are combined, equipped with 65 flat screen TV and Blu-ray player. ( Maximum 4 Guests).

🛏 2 beds · 👥 4 guests
$272 /night
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Oceanview Penthouse, in VIllage, 30-steps to Best Beach, Tiki-Bar, Free Bikes and Paddle-boards! Siesta Key, Florida

Oceanview Penthouse, in VIllage, 30-steps to Best Beach, Tiki-Bar, Free Bikes and Paddle-boards!

Located in Siesta Key, Florida, United States. Oceanview Penthouse, in VIllage, 30-steps to Best Beach, Tiki-Bar, Free Bikes and Paddle-boards! The Oceanview 603 Penthouse is a Gertrude Rentals property right on Beach Rd at Access 10. Large, Fully Renovated, Top Floor Ocean-View 3BR Apartment, just 13 steps to "beach-front", in the world-famous Siesta Key Village! Spend your days soaking in Sun and Seabreeze's at the worlds #1 Beach, and evenings lounging dining and drinking alfresco at your choice of 20 fantastic restaurants. Just a 9 second walk to the beach path and an 8-minute walk or 1 minute ride on the free trolley to the best shopping, dining, and entertainment on the island. Sure to provide a combination of fun and relaxation you can't get in other getaways. 603 SIESTA KEY OCEANVIEW PENTHOUSE “AT A GLANCE”- Ocean/beach views and southerly exposure from living room and bedroom.- 15 steps from yard to access/path for Siesta Key's Best Beach and clear calm Azure Water & pure quartz White Sand!- Short walk or bike to the V

🛏 3 beds · 👥 10 guests
$565 /night
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Monarch Villa |  Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach! Siesta Key, Florida

Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Located in Siesta Key, Florida, United States. Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach! Welcome to Monarch Villa, an exquisite Siesta Key retreat that offers a unique opportunity for a customizable vacation experience. This magnificent property can be rented separately or as a whole - Casa De Mariposa. Whether you're traveling with a large group or looking for a more intimate stay, Monarch Villa has the perfect accommodations for you.Inside, this vacation rental duplex features three bedrooms and three full bathrooms, ensuring privacy and convenience for every guest. With two king beds, two twin beds, and one sleeper sofa, Monarch Villa can comfortably accommodate up to 8 guests. High-quality linens are provided for a restful and enjoyable stay.The property features four spacious balconies, providing additional outdoor living spaces where you can relax, unwind, and enjoy the coastal breeze. The breathtaking Gulf views from the second and third-floor balconies of the beach-facing unit will

🛏 3 beds · 👥 8 guests
$383 /night
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SIESTA KEY  BEACH , ROMANTIC UNIT C Siesta Key, Florida

SIESTA KEY BEACH , ROMANTIC UNIT C

Located in Siesta Key, Florida, United States. SIESTA KEY BEACH , ROMANTIC UNIT C 100 feet to the beach! Max 2 people & 1 car!This is the BEST VALUE with the LOCATION YOU CAN FIND!!! THIS NEIGHBORHOOD WILL MAKE YOU FEEL LIKE A MILLION DOLLARS PROVIDES AN UNMATCHED BEACH ATMOSPHERE!! Very good Beach house atmosphere! This house is not new, but very clean and everything works perfectly! the perfect location - across from the beach and within walking distance to so many restaurants and bars. It is great to be able to quickly run back to the house to take a break from the sun or restock the cooler The perfect location is right across from the beach provides walking distance access to so many restaurants or bars in the Village and heart of Siesta Key right on the country's #1 beach in the nation. That being said the location also provides the opportunity to quickly walk back to the house to get in the shade from the sun or just to even restock the cooler. In addition to the variety of bars, restaurants, nightlife with live music, and

🛏 1 bed · 👥 2 guests
$125 /night
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Kid Friendly Island Home In Paradise!! Siesta Key, Florida

Kid Friendly Island Home In Paradise!!

Located in Siesta Key, Florida, United States. Kid Friendly Island Home In Paradise!! Kid-friendly, single family home, 4 bedrooms with 2 sofa sleeper beds, 2 baths, heated outside pool(set to 82 degrees) with child fencing around the pool area. Pool is cleaned once a week, please note that with rain, wind ect the pool will get debris in it. A pool net is provided to clean pool. Have dinner/cocktails at the Tiki bar by the pool or practice your putting on our putting course in the front yard. Please note golf cart and boat not included. Short walking distance to 15 great restaurants, 12 bars, many, many shops, bike and scooter rental, wash and fold, and more.... Short drive to many sites, golf courses and much more. Siesta key beach is on travel channel for top ten beaches in the world....Local beach is approx 3 blocks, and can be walked. Public beach is further, however, many 'free ride' golf cart services are available and work for tips only. They will pick you up at your home and take you to the beach. The "free" rides are a l

🛏 4 beds · 👥 8 guests
$274 /night
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Peacock Villa |  Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach! Siesta Key, Florida

Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Located in Siesta Key, Florida, United States. Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach! Welcome to Peacock Villa, an exquisite Siesta Key retreat that offers a unique opportunity for a customizable vacation experience. This magnificent property can be rented separately or as a whole - Casa De Mariposa. Whether you're traveling with a large group or looking for a more intimate stay, Peacock Villa has the perfect accommodations for you.Inside, this vacation rental duplex features three bedrooms and three full bathrooms, ensuring privacy and convenience for every guest. With two king beds, two twin beds, and one sleeper sofa, Peacock Villa can comfortably accommodate up to 8 guests. High-quality linens are provided for a restful and enjoyable stay.The property features two spacious balconies, providing additional outdoor living spaces where you can relax, unwind, and enjoy the coastal breeze.With a full kitchen at your disposal, you will be equipped with everything you need to prep

🛏 3 beds · 👥 8 guests
$306 /night
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Luxury Pool and Rooftop Deck, Walk to Siesta Key Beach & Village! - Casa Siesta Siesta Key, Florida

Luxury Pool and Rooftop Deck, Walk to Siesta Key Beach & Village! - Casa Siesta

Located in Siesta Key, Florida, United States. Luxury Pool and Rooftop Deck, Walk to Siesta Key Beach & Village! - Casa Siesta Casa Siesta by Siesta Key Luxury Rental Properties Home in Siesta Key, FloridaSiesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key!Welcome to Casa Siesta, a stunning three-bedroom, three-bath mission-styled vacation home just steps from the beautiful Siesta Key Beach and the vibrant Siesta Key Village. This elegant retreat is perfect for family and friends, offering comfort and privacy as each bedroom is a complete suite. Highlights • 1-minute walk from the beach • 3-minute walk to shopping and dining • Private pool with in-ground spa • Rooftop deck with breathtaking beach views • Professional linen program • BBQ grill and outdoor seating Casa Siesta features a private pool with an in-ground spa, a rooftop deck with breathtaking beach views, a BBQ grill, and outdoor seating in a beautifully landscaped courtyard. Inside, the coastal-chic great room features

🛏 3 beds · 👥 8 guests
$606 /night
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Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶 Siesta Key, Florida

Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶

Located in Siesta Key, Florida, United States. Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶 Step into the exclusive embrace of Luxe Lagoon, where Siesta Key's charm intertwines with a sophisticated retreat. This haven of indulgence, designed for the connoisseur of luxury, unfolds with 7 bedrooms, 7 full bathrooms, and 2 half bathrooms - inviting up to 20 guests to experience an unparalleled fusion of elegance and comfort.As you venture into the backyard, a shimmering oasis emerges—a private sanctuary cocooned by swaying palms, transporting you to a tropical reverie. The private heated pool and spa beckon, inviting you to immerse yourself in their sparkling embrace, while the manicured putting green and engaging ping pong table promise endless amusement without stepping beyond the property's confines. As a convience for your group, one half bath is located on this first floor providing ease of access.Ascend the stairs or ascend effortlessly with the private elevator, revealing a second floor t

🛏 7 beds · 👥 22 guests
$1,239 /night
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The Little Sandy...#1 in Siesta! Siesta Key, Florida

The Little Sandy...#1 in Siesta!

Located in Siesta Key, Florida, United States. The Little Sandy...#1 in Siesta! You need a vacation and we've got just the place!Nestled amongst two ancient banyan trees, The Little Sandy rests on a quiet tropical street, phenomenally located just one block from the best beach in America! Take a look at the map...we're only 400 feet away from the beach access! Not only are we super-close to the beach, but we're only 1.5 blocks to town...close enough to make it a quick walk, without having to deal with the crowds, all day...and all night!Inside, the sun-filled rooms are tastefully decorated in tropical chic. White plantation shutters, sea-foam walls and a southwestern exposure bathes everything in a soft, beautiful sunlight. There's plenty of space for the kids and the open plan kitchen makes mealtime a breeze. Hi-speed Wi-Fi will keep you in close contact with the rest of the world, but we won't tell anyone if you turn it off! It can be hard to find a spot for your car on Siesta Key, but we've got you covered with dedicated

🛏 2 beds · 👥 6 guests
$257 /night
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The Blue Door-Luxury 4BD w/Full Gulf views, private beach access&walk to town! Siesta Key, Florida

The Blue Door-Luxury 4BD w/Full Gulf views, private beach access&walk to town!

Located in Siesta Key, Florida, United States. The Blue Door-Luxury 4BD w/Full Gulf views, private beach access&walk to town! Newly renovated and first time on the market for this 4 bedroom, 3 bathroom spacious 2-floor unit with beautiful unobstructed views of the. Bring the whole family to this great place with lots of room for fun and convenient beach access. Beautiful views to make memories to last a life time. Two full frontal decks to take in all the gulf has to offer. The first deck has table chairs, grill and lounge chairs. The top deck has rocking chairs with side table to watch the gulf, read a book or get some sun. There is a beach in front of the building to enjoy, in addition to a private beach path down to the waters edge. Dogs are allowed on a case by case basis with $175 fe. No cats allowed, as I'm allergic. Walking distance to the beach, public beach and a half mile to the Village. Walk down your private access to the beach and explore the amazing shells and sands of Siesta Beach. Continue south to the public bea

🛏 4 beds · 👥 10 guests
$1,092 /night
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Heron House | Pet Friendly, Walk to Siesta Key Beach & Village in 2 mins! Siesta Key, Florida

Heron House | Pet Friendly, Walk to Siesta Key Beach & Village in 2 mins!

Located in Siesta Key, Florida, United States. Heron House | Pet Friendly, Walk to Siesta Key Beach & Village in 2 mins! Welcome to Heron House, an exclusive retreat in the heart of Siesta Key Village, where laid-back luxury meets coastal convenience. This duplex property just half a block from the pristine shores of Siesta Key Beach, this 3-bedroom, 3-bath haven invites you to experience the best of beachside living. Indulge in the privacy of your own heated swim spa at Heron House, a perfect oasis to unwind after a day of sun-soaked adventures. The prime location places you right in the vibrant Siesta Key Village, ensuring you're just steps away from an array of restaurants, bars, shops, and entertainment options. Convenience meets luxury as you enjoy easy access to the vibrant energy of the village and the breathtaking beauty of Siesta Key Beach.This thoughtfully designed units, Heron House, accommodates up to 12 guests, offering 3 bedrooms featuring 2 King beds, 2 Full beds, and 2 Full sleeper sofas, each adorned with provided

🛏 3 beds · 👥 10 guests
$437 /night
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[lounge like locals] walk to siesta beach +bikes Siesta Key, Florida

[lounge like locals] walk to siesta beach +bikes

Located in Siesta Key, Florida, United States. [lounge like locals] walk to siesta beach +bikes The whole group will enjoy easy access to everything from this centrally located place. Relax and recharge in this elevated two bedroom home. The high ceilings bring in plentiful natural sunlight with direct access to a private oversized deck. The bright and spacious layout provides plenty of space for families or couples traveling to the beach. Both Siesta Key village and Beach access 7 are less than 1/2 mile from the home. 2 bikes are available onsite ($40 each rental charge by Venmo) The interior is tastefully designed with functional decor. Please note this home is not suitable for young children due to the steep stairs at the entrance. Also there is a separate air Bnb unit below, there are no shared spaces. laundry room is shared with unit below and is located in garage available daily 4-9 pm . Through air Bnb messenger or in person. Siesta key village Bike/ walk /car/ Uber Please park in front of the garage towards the right side

🛏 2 beds · 👥 4 guests
$231 /night
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Siesta Key beach house Siesta Key, Florida

Siesta Key beach house

Located in Siesta Key, Florida, United States. Siesta Key beach house Nice house with private pool with tree bedrooms and tree bath close to Siesta Key Village resturants and Beach. Canal on the backyard there you can relax and fishing or have your barbecue. Perfekt place for you and your family.

🛏 3 beds · 👥 6 guests
$342 /night
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2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach Siesta Key, Florida

2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

Located in Siesta Key, Florida, United States. 2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach This charming tropical 1,320 2 bedroom 2 bath home is located within the heart of Siesta Key Village and a block away from the famous Siesta Key Beach. This private beach home will have you relaxed from the moment you kick off your flip flops. The home is equipped with 3 4K smart TVs and a ton of beach toys, chairs to keep traveling easy.

🛏 3 beds · 👥 6 guests
$223 /night
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**Beach, Village, Canal, Dock & Private Heated Pool!! Siesta Key, Florida

**Beach, Village, Canal, Dock & Private Heated Pool!!

Located in Siesta Key, Florida, United States. **Beach, Village, Canal, Dock & Private Heated Pool!! HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the first time. If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot. Welcome.... From the minute you arrive at the "RCC" (Rad's Cozy Cottage on Canal) in Siesta Village you will soon know you have arrived in a special place. You will be able to completely relax and count this as one of your best vacations or getaways ever! From the quaint enclosed front porch, you will begin to relax and enjoy your view of the famous Siesta Key canal on the outer rim of "Palm Island," watch the Siesta Village Trolley and people pass by just relaxing.This is a true Gem in Siesta Key that has new electric and we h

🛏 2 beds · 👥 6 guests
$395 /night
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Pineapple Paradise | 1 Block from Beach, Community Pool, Resort Style Amenities! ☀️ Siesta Key, Florida

Pineapple Paradise | 1 Block from Beach, Community Pool, Resort Style Amenities! ☀️

Located in Siesta Key, Florida, United States. Pineapple Paradise | 1 Block from Beach, Community Pool, Resort Style Amenities! ☀️ Introducing Pineapple Paradise: Your Exclusive Oasis Just Steps from Siesta Key Beach!Indulge in tranquility at Pineapple Paradise, a serene hideaway nestled just one block away from the acclaimed Siesta Key Beach, honored as the #1 beach in the USA. This exceptional vacation rental duplex offers the perfect fusion of convenience and relaxation, with effortless access to the beach, Siesta Key Village, and an array of resort-style amenities.The Space:Discover pure relaxation at Pineapple Paradise, an oasis of comfort and coastal elegance. Recently renovated, this retreat exudes modern charm with sleek furnishings and vibrant decor throughout. The fully equipped kitchen invites culinary exploration, while the sleek bathroom offers a rejuvenating sanctuary. Unwind in the inviting living area or soak up the Florida sunshine at your resort style pool.Guest Access:At Pineapple Paradise, you'll enjoy access to

🛏 2 beds · 👥 8 guests
$269 /night
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SKV 309 - Heated ❤ Pool, Close to Beach, Village, Restaurants, Bars, Shopping!! Siesta Key, Florida

SKV 309 - Heated ❤ Pool, Close to Beach, Village, Restaurants, Bars, Shopping!!

Located in Siesta Key, Florida, United States. SKV 309 - Heated ❤ Pool, Close to Beach, Village, Restaurants, Bars, Shopping!! Looking for the ultimate Siesta Key experience? This is it!! Located just South of Morton's in Siesta Key Village. Only 10 min walk to Beach! Heated Pool, Smart TVs w/ Strong WIFI in every room. Comfy beds, fully-stocked kitchen will easily sleep 6. Restaurants, Bars, Seafood, Night Clubs, Big Olaf, Bike rentals, Live Music & so much more -- it's all here. No car needed. Free trolley leaves Morton's every 30 min to take you up and down the Key. You will absolutely love it here!NOTE: BOOKING FEBRUARY? Please book ENTIRE month only NOT mid-month to mid-month. This time frame is a monthly minimum property and we don't want to be empty for part of the time. Booking February 1 - February 28? Okay. Want to book February 15 - March 15? Not okay. Please ask first if you are unsure. We will try and work with you. Thanks in advance.The spaceYour Vacation Home near the HEART of Siesta Key Village!This centrally-locat

🛏 2 beds · 👥 6 guests
$175 /night
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Location. 3 bedroom cottage block from beach and two blocks from Siesta Village Siesta Key, Florida

Location. 3 bedroom cottage block from beach and two blocks from Siesta Village

Located in Siesta Key, Florida, United States. Location. 3 bedroom cottage block from beach and two blocks from Siesta Village Location, location, location. Our charming 3-bedroom 2 bath Florida beach cottage, which is over 1000 feet and sleeps 6, which we call the “Manatee Cottage” is across the street from the soft, white sands of the world-famous Siesta Beach which is consistently rated the best beach in the United States (you will be a 5 minute walk from access 7). Enjoy the amazing sunsets each night of your stay without the hassles of traffic, parking and crowds. You will also be 2 blocks from Siesta Village with its numerous restaurants, bars and shops. Park your car and forget about driving as you walk or bike and feel like a local as you enjoy our special piece of heaven.Downtown Sarasota, which is a brief ride or Uber away, is world renowned and known for its cultural institutions, gourmet restaurants, art galleries, theater, the John and Mable Ringling Museum of Art, and the Ringlings’ breathtaking home, Ca’d’Zan on Sar

🛏 3 beds · 👥 6 guests
$328 /night
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Resort Style Backyard! Private Dock and Beach Views! - Sea Spray Siesta Key, Florida

Resort Style Backyard! Private Dock and Beach Views! - Sea Spray

Located in Siesta Key, Florida, United States. Resort Style Backyard! Private Dock and Beach Views! - Sea Spray Sea Spray by Siesta Key Luxury Rental PropertiesHome in Siesta Key, FloridaWelcome to Sea Spray! This eight-bedroom and six-and-a-half-bathroom home will check off all the boxes for your desired Siesta Key rental. It is a short walk to Siesta Key Beach and within walking distance to Downtown Siesta Key Village Area. So, catch some sunshine at the beach or enjoy great live music, dining, or shopping in the village. Highlights• Private Dock • Rooftop Deck• Beach Views• Less than a 5-minute walk to the beach• Private Pool with Waterslide and In-ground Spa• Ping Pong• Foosball table• Convenient location near dining and shopping• Dog friendly with approval and additional feeThe spectacular backyard is built like a private waterpark with a Private Resort Style Heated Pool featuring a Rock Water Slide, Waterfall, Grotto, Swim-up bar, Sun Shelf, and Spa. You’ll love the lounge chairs, dining options, and BBQ grill. Just across t

🛏 8 beds · 👥 22 guests
$1,012 /night
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Full Ocean Views w/Private Beach on Siesta Key, Heated Pool

Siesta Key, Florida

Full Ocean Views w/Private Beach on Siesta Key, Heated Pool

🛏 2 bed · 👥 4 guests

Located in Siesta Key, Florida, United States. Full Ocean Views w/Private Beach on Siesta Key, Heated Pool This beautiful 15th floor, 2 bedroom 2 bathroom condo offers full ocean and beach views throughout and is just steps from its private beach Siesta Key Beach in Siesta Key! This condo is almost 1200 sq. ft. being 1/4 of the entire 15th floor is located right on Siesta Key Beach, #1 rated beach in the USA with gulf views, bay views, city light views, Big Pass Lido Key Beach views. The Terrace has a gorgeous heated pool overlooking the ocean, game room & fitness center, community room, and your own numbered covered parking space, just steps to Siesta Key Village with plenty of dinging and shops.Terrace on the Beach Highlights:Corner Unit Condo Facing W/NW for Full Ocean Views ThroughoutStacked Sliders Open Wide to Open-Air Balconies (no screens!)Ocean Views from Bedrooms, Living & Dining RoomsKing Ensuite Master, Balcony w/Ocean Views, Cable Flat Screen TVGuest Ensuite Bedroom with 2 Twin Beds, Balcony w/ Ocean Views (no TV)alle

$192

/ night

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Private house, Heated Pool, Pet friendly-walk to beach

Siesta Key, Florida

Private house, Heated Pool, Pet friendly-walk to beach

🛏 3 bed · 👥 6 guests

Located in Siesta Key, Florida, United States. Private house, Heated Pool, Pet friendly-walk to beach Come and enjoy this pet friendly private house with your very own secluded heated swimming pool, in beautiful Siesta Key. Our Siesta Key Tropical Pool Paradise home is a 5 Min walk to the #1 Rated Beach with the best white sands you have ever seen. 10 Min walk to the village where you will find great local restaurants, your choice of ice cream shops, live music, village grocery store and liquor store - you won't need to head to the main land. Our renovated house offers you a home away from home with a full kitchen at your disposal if you choose to eat in. Our in ground heated pool is surrounded by a lush tropical oasis. We have completely renovated our house and are so happy to share our new and improved vacation home with you. This is the place you'll want visit, and return year after year. Check in times is 4 PM and check out time is 10 AM.*** Please Check out our other listing #1085215, also on Siesta Key, just two streets a

$194

/ night

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Lovely Rental in Siesta Key Village! Walk to Beach

Siesta Key, Florida

Lovely Rental in Siesta Key Village! Walk to Beach

🛏 2 bed · 👥 6 guests

Located in Siesta Key, Florida, United States. Lovely Rental in Siesta Key Village! Walk to Beach This lovely updated condo lies in the heart of Siesta Key Village!! Perfect Location!! Adorable condo updated, light & bright is now available and ready for you. Minorga Complex in Siesta Key Village includes a community heated pool with only an 8 minute walk to the beach! Your choice of cafe's, restaurants, shops and nightlight are all only steps away from the end unit condo. Walk to a local's favorite, The Salty Dog, for a grouper sandwich and an ice cold beer, or Solorzano's Pizza, another fave only a 3 minute walk and the Beach Club Nightclub has live entertainment along with pool tables.....all just around the corner. Only an 8 minute walk to sink your toes in the white famous powdery sands of the Gulf of Mexico where you can lie under an umbrella and relax with a good book and cold drink! (walk to your choice of Public beach accesses) #3 and #5 are just 0.4 miles (8 minute walk) and #2 & #4 are just 0.5 miles (9 minute wa

$188

/ night

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Siesta Key Village - Townhouse - Heated Pool - Beach Walkable!

Siesta Key, Florida

Siesta Key Village - Townhouse - Heated Pool - Beach Walkable!

🛏 3 bed · 👥 10 guests

Located in Siesta Key, Florida, United States. Siesta Key Village - Townhouse - Heated Pool - Beach Walkable! Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.This two-story townhouse style location, Siesta Key Dream’s closest unit to the Village, includes 3 spacious bedrooms that are perfect for up to 10 guests. On the first floor, you’ll experience an open floor plan connecting a welcoming living room, a dining room that seats 6, and kitchen featuring stainless steel appliances. On the second floor, you’ll find three bedrooms and two bathrooms. The main bedroom has an in-room bathroom, tub with jets, and a walk

$385

/ night

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Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach

Siesta Key, Florida

Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach

🛏 4 bed · 👥 8 guests

Located in Siesta Key, Florida, United States. Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach Welcome to Siesta Soul, a captivating retreat located just steps from the vibrant Siesta Key Village. This enchanting vacation home offers an ideal location and a backyard oasis, providing the perfect blend of convenience and relaxation for your Siesta Key getaway.Siesta Soul features four bedrooms and three full baths, including a master bedroom for added privacy and luxury. The master bedroom is a tranquil retreat with a comfortable king bed, providing a peaceful sanctuary for restful nights. The remaining three bedrooms offer queen beds, ensuring a comfortable night's sleep for everyone. Linens are provided for all beds, allowing you to simply relax and unwind upon your arrival.On the main level, you will greeted by a spacious living room and open kitchen that seamlessly connect together, creating the perfect space for entertaining and gathering with loved ones. The open floor plan e

$404

/ night

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Cabana Cottage Across street from Beach  and  Heated Pool

Siesta Key, Florida

Cabana Cottage Across street from Beach and Heated Pool

🛏 2 bed · 👥 4 guests

Located in Siesta Key, Florida, United States. Cabana Cottage Across street from Beach and Heated Pool The Cabana is small but mighty! A fully equipped kitchen complete with granite countertops, and a breakfast bar, with all of the comforts of home.The master bedroom has a King size Serta ICOMFORT Memory Foam Gel bed with a flat screen TV, and an attached European Rain shower bath. The second bedroom is two, twin Serta ICOMFORT Memory Foam Gel beds with a flat screen TV. The second tub/shower bathroom is off the kitchen area. Living room and dining areas are combined, equipped with 65 flat screen TV and Blu-ray player. ( Maximum 4 Guests).

$272

/ night

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Oceanview Penthouse, in VIllage, 30-steps to Best Beach, Tiki-Bar, Free Bikes and Paddle-boards!

Siesta Key, Florida

Oceanview Penthouse, in VIllage, 30-steps to Best Beach, Tiki-Bar, Free Bikes and Paddle-boards!

🛏 3 bed · 👥 10 guests

Located in Siesta Key, Florida, United States. Oceanview Penthouse, in VIllage, 30-steps to Best Beach, Tiki-Bar, Free Bikes and Paddle-boards! The Oceanview 603 Penthouse is a Gertrude Rentals property right on Beach Rd at Access 10. Large, Fully Renovated, Top Floor Ocean-View 3BR Apartment, just 13 steps to "beach-front", in the world-famous Siesta Key Village! Spend your days soaking in Sun and Seabreeze's at the worlds #1 Beach, and evenings lounging dining and drinking alfresco at your choice of 20 fantastic restaurants. Just a 9 second walk to the beach path and an 8-minute walk or 1 minute ride on the free trolley to the best shopping, dining, and entertainment on the island. Sure to provide a combination of fun and relaxation you can't get in other getaways. 603 SIESTA KEY OCEANVIEW PENTHOUSE “AT A GLANCE”- Ocean/beach views and southerly exposure from living room and bedroom.- 15 steps from yard to access/path for Siesta Key's Best Beach and clear calm Azure Water & pure quartz White Sand!- Short walk or bike to the V

$565

/ night

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Monarch Villa |  Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Siesta Key, Florida

Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

🛏 3 bed · 👥 8 guests

Located in Siesta Key, Florida, United States. Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach! Welcome to Monarch Villa, an exquisite Siesta Key retreat that offers a unique opportunity for a customizable vacation experience. This magnificent property can be rented separately or as a whole - Casa De Mariposa. Whether you're traveling with a large group or looking for a more intimate stay, Monarch Villa has the perfect accommodations for you.Inside, this vacation rental duplex features three bedrooms and three full bathrooms, ensuring privacy and convenience for every guest. With two king beds, two twin beds, and one sleeper sofa, Monarch Villa can comfortably accommodate up to 8 guests. High-quality linens are provided for a restful and enjoyable stay.The property features four spacious balconies, providing additional outdoor living spaces where you can relax, unwind, and enjoy the coastal breeze. The breathtaking Gulf views from the second and third-floor balconies of the beach-facing unit will

$383

/ night

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SIESTA KEY  BEACH , ROMANTIC UNIT C

Siesta Key, Florida

SIESTA KEY BEACH , ROMANTIC UNIT C

🛏 1 bed · 👥 2 guests

Located in Siesta Key, Florida, United States. SIESTA KEY BEACH , ROMANTIC UNIT C 100 feet to the beach! Max 2 people & 1 car!This is the BEST VALUE with the LOCATION YOU CAN FIND!!! THIS NEIGHBORHOOD WILL MAKE YOU FEEL LIKE A MILLION DOLLARS PROVIDES AN UNMATCHED BEACH ATMOSPHERE!! Very good Beach house atmosphere! This house is not new, but very clean and everything works perfectly! the perfect location - across from the beach and within walking distance to so many restaurants and bars. It is great to be able to quickly run back to the house to take a break from the sun or restock the cooler The perfect location is right across from the beach provides walking distance access to so many restaurants or bars in the Village and heart of Siesta Key right on the country's #1 beach in the nation. That being said the location also provides the opportunity to quickly walk back to the house to get in the shade from the sun or just to even restock the cooler. In addition to the variety of bars, restaurants, nightlife with live music, and

$125

/ night

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Kid Friendly Island Home In Paradise!!

Siesta Key, Florida

Kid Friendly Island Home In Paradise!!

🛏 4 bed · 👥 8 guests

Located in Siesta Key, Florida, United States. Kid Friendly Island Home In Paradise!! Kid-friendly, single family home, 4 bedrooms with 2 sofa sleeper beds, 2 baths, heated outside pool(set to 82 degrees) with child fencing around the pool area. Pool is cleaned once a week, please note that with rain, wind ect the pool will get debris in it. A pool net is provided to clean pool. Have dinner/cocktails at the Tiki bar by the pool or practice your putting on our putting course in the front yard. Please note golf cart and boat not included. Short walking distance to 15 great restaurants, 12 bars, many, many shops, bike and scooter rental, wash and fold, and more.... Short drive to many sites, golf courses and much more. Siesta key beach is on travel channel for top ten beaches in the world....Local beach is approx 3 blocks, and can be walked. Public beach is further, however, many 'free ride' golf cart services are available and work for tips only. They will pick you up at your home and take you to the beach. The "free" rides are a l

$274

/ night

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Peacock Villa |  Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Siesta Key, Florida

Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

🛏 3 bed · 👥 8 guests

Located in Siesta Key, Florida, United States. Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach! Welcome to Peacock Villa, an exquisite Siesta Key retreat that offers a unique opportunity for a customizable vacation experience. This magnificent property can be rented separately or as a whole - Casa De Mariposa. Whether you're traveling with a large group or looking for a more intimate stay, Peacock Villa has the perfect accommodations for you.Inside, this vacation rental duplex features three bedrooms and three full bathrooms, ensuring privacy and convenience for every guest. With two king beds, two twin beds, and one sleeper sofa, Peacock Villa can comfortably accommodate up to 8 guests. High-quality linens are provided for a restful and enjoyable stay.The property features two spacious balconies, providing additional outdoor living spaces where you can relax, unwind, and enjoy the coastal breeze.With a full kitchen at your disposal, you will be equipped with everything you need to prep

$306

/ night

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Luxury Pool and Rooftop Deck, Walk to Siesta Key Beach & Village! - Casa Siesta

Siesta Key, Florida

Luxury Pool and Rooftop Deck, Walk to Siesta Key Beach & Village! - Casa Siesta

🛏 3 bed · 👥 8 guests

Located in Siesta Key, Florida, United States. Luxury Pool and Rooftop Deck, Walk to Siesta Key Beach & Village! - Casa Siesta Casa Siesta by Siesta Key Luxury Rental Properties Home in Siesta Key, FloridaSiesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key!Welcome to Casa Siesta, a stunning three-bedroom, three-bath mission-styled vacation home just steps from the beautiful Siesta Key Beach and the vibrant Siesta Key Village. This elegant retreat is perfect for family and friends, offering comfort and privacy as each bedroom is a complete suite. Highlights • 1-minute walk from the beach • 3-minute walk to shopping and dining • Private pool with in-ground spa • Rooftop deck with breathtaking beach views • Professional linen program • BBQ grill and outdoor seating Casa Siesta features a private pool with an in-ground spa, a rooftop deck with breathtaking beach views, a BBQ grill, and outdoor seating in a beautifully landscaped courtyard. Inside, the coastal-chic great room features

$606

/ night

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Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶

Siesta Key, Florida

Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶

🛏 7 bed · 👥 22 guests

Located in Siesta Key, Florida, United States. Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶 Step into the exclusive embrace of Luxe Lagoon, where Siesta Key's charm intertwines with a sophisticated retreat. This haven of indulgence, designed for the connoisseur of luxury, unfolds with 7 bedrooms, 7 full bathrooms, and 2 half bathrooms - inviting up to 20 guests to experience an unparalleled fusion of elegance and comfort.As you venture into the backyard, a shimmering oasis emerges—a private sanctuary cocooned by swaying palms, transporting you to a tropical reverie. The private heated pool and spa beckon, inviting you to immerse yourself in their sparkling embrace, while the manicured putting green and engaging ping pong table promise endless amusement without stepping beyond the property's confines. As a convience for your group, one half bath is located on this first floor providing ease of access.Ascend the stairs or ascend effortlessly with the private elevator, revealing a second floor t

$1,239

/ night

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The Little Sandy...#1 in Siesta!

Siesta Key, Florida

The Little Sandy...#1 in Siesta!

🛏 2 bed · 👥 6 guests

Located in Siesta Key, Florida, United States. The Little Sandy...#1 in Siesta! You need a vacation and we've got just the place!Nestled amongst two ancient banyan trees, The Little Sandy rests on a quiet tropical street, phenomenally located just one block from the best beach in America! Take a look at the map...we're only 400 feet away from the beach access! Not only are we super-close to the beach, but we're only 1.5 blocks to town...close enough to make it a quick walk, without having to deal with the crowds, all day...and all night!Inside, the sun-filled rooms are tastefully decorated in tropical chic. White plantation shutters, sea-foam walls and a southwestern exposure bathes everything in a soft, beautiful sunlight. There's plenty of space for the kids and the open plan kitchen makes mealtime a breeze. Hi-speed Wi-Fi will keep you in close contact with the rest of the world, but we won't tell anyone if you turn it off! It can be hard to find a spot for your car on Siesta Key, but we've got you covered with dedicated

$257

/ night

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The Blue Door-Luxury 4BD w/Full Gulf views, private beach access&walk to town!

Siesta Key, Florida

The Blue Door-Luxury 4BD w/Full Gulf views, private beach access&walk to town!

🛏 4 bed · 👥 10 guests

Located in Siesta Key, Florida, United States. The Blue Door-Luxury 4BD w/Full Gulf views, private beach access&walk to town! Newly renovated and first time on the market for this 4 bedroom, 3 bathroom spacious 2-floor unit with beautiful unobstructed views of the. Bring the whole family to this great place with lots of room for fun and convenient beach access. Beautiful views to make memories to last a life time. Two full frontal decks to take in all the gulf has to offer. The first deck has table chairs, grill and lounge chairs. The top deck has rocking chairs with side table to watch the gulf, read a book or get some sun. There is a beach in front of the building to enjoy, in addition to a private beach path down to the waters edge. Dogs are allowed on a case by case basis with $175 fe. No cats allowed, as I'm allergic. Walking distance to the beach, public beach and a half mile to the Village. Walk down your private access to the beach and explore the amazing shells and sands of Siesta Beach. Continue south to the public bea

$1,092

/ night

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Heron House | Pet Friendly, Walk to Siesta Key Beach & Village in 2 mins!

Siesta Key, Florida

Heron House | Pet Friendly, Walk to Siesta Key Beach & Village in 2 mins!

🛏 3 bed · 👥 10 guests

Located in Siesta Key, Florida, United States. Heron House | Pet Friendly, Walk to Siesta Key Beach & Village in 2 mins! Welcome to Heron House, an exclusive retreat in the heart of Siesta Key Village, where laid-back luxury meets coastal convenience. This duplex property just half a block from the pristine shores of Siesta Key Beach, this 3-bedroom, 3-bath haven invites you to experience the best of beachside living. Indulge in the privacy of your own heated swim spa at Heron House, a perfect oasis to unwind after a day of sun-soaked adventures. The prime location places you right in the vibrant Siesta Key Village, ensuring you're just steps away from an array of restaurants, bars, shops, and entertainment options. Convenience meets luxury as you enjoy easy access to the vibrant energy of the village and the breathtaking beauty of Siesta Key Beach.This thoughtfully designed units, Heron House, accommodates up to 12 guests, offering 3 bedrooms featuring 2 King beds, 2 Full beds, and 2 Full sleeper sofas, each adorned with provided

$437

/ night

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[lounge like locals] walk to siesta beach +bikes

Siesta Key, Florida

[lounge like locals] walk to siesta beach +bikes

🛏 2 bed · 👥 4 guests

Located in Siesta Key, Florida, United States. [lounge like locals] walk to siesta beach +bikes The whole group will enjoy easy access to everything from this centrally located place. Relax and recharge in this elevated two bedroom home. The high ceilings bring in plentiful natural sunlight with direct access to a private oversized deck. The bright and spacious layout provides plenty of space for families or couples traveling to the beach. Both Siesta Key village and Beach access 7 are less than 1/2 mile from the home. 2 bikes are available onsite ($40 each rental charge by Venmo) The interior is tastefully designed with functional decor. Please note this home is not suitable for young children due to the steep stairs at the entrance. Also there is a separate air Bnb unit below, there are no shared spaces. laundry room is shared with unit below and is located in garage available daily 4-9 pm . Through air Bnb messenger or in person. Siesta key village Bike/ walk /car/ Uber Please park in front of the garage towards the right side

$231

/ night

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Siesta Key beach house

Siesta Key, Florida

Siesta Key beach house

🛏 3 bed · 👥 6 guests

Located in Siesta Key, Florida, United States. Siesta Key beach house Nice house with private pool with tree bedrooms and tree bath close to Siesta Key Village resturants and Beach. Canal on the backyard there you can relax and fishing or have your barbecue. Perfekt place for you and your family.

$342

/ night

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2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

Siesta Key, Florida

2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

🛏 3 bed · 👥 6 guests

Located in Siesta Key, Florida, United States. 2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach This charming tropical 1,320 2 bedroom 2 bath home is located within the heart of Siesta Key Village and a block away from the famous Siesta Key Beach. This private beach home will have you relaxed from the moment you kick off your flip flops. The home is equipped with 3 4K smart TVs and a ton of beach toys, chairs to keep traveling easy.

$223

/ night

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**Beach, Village, Canal, Dock & Private Heated Pool!!

Siesta Key, Florida

**Beach, Village, Canal, Dock & Private Heated Pool!!

🛏 2 bed · 👥 6 guests

Located in Siesta Key, Florida, United States. **Beach, Village, Canal, Dock & Private Heated Pool!! HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the first time. If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot. Welcome.... From the minute you arrive at the "RCC" (Rad's Cozy Cottage on Canal) in Siesta Village you will soon know you have arrived in a special place. You will be able to completely relax and count this as one of your best vacations or getaways ever! From the quaint enclosed front porch, you will begin to relax and enjoy your view of the famous Siesta Key canal on the outer rim of "Palm Island," watch the Siesta Village Trolley and people pass by just relaxing.This is a true Gem in Siesta Key that has new electric and we h

$395

/ night

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Pineapple Paradise | 1 Block from Beach, Community Pool, Resort Style Amenities! ☀️

Siesta Key, Florida

Pineapple Paradise | 1 Block from Beach, Community Pool, Resort Style Amenities! ☀️

🛏 2 bed · 👥 8 guests

Located in Siesta Key, Florida, United States. Pineapple Paradise | 1 Block from Beach, Community Pool, Resort Style Amenities! ☀️ Introducing Pineapple Paradise: Your Exclusive Oasis Just Steps from Siesta Key Beach!Indulge in tranquility at Pineapple Paradise, a serene hideaway nestled just one block away from the acclaimed Siesta Key Beach, honored as the #1 beach in the USA. This exceptional vacation rental duplex offers the perfect fusion of convenience and relaxation, with effortless access to the beach, Siesta Key Village, and an array of resort-style amenities.The Space:Discover pure relaxation at Pineapple Paradise, an oasis of comfort and coastal elegance. Recently renovated, this retreat exudes modern charm with sleek furnishings and vibrant decor throughout. The fully equipped kitchen invites culinary exploration, while the sleek bathroom offers a rejuvenating sanctuary. Unwind in the inviting living area or soak up the Florida sunshine at your resort style pool.Guest Access:At Pineapple Paradise, you'll enjoy access to

$269

/ night

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SKV 309 - Heated ❤ Pool, Close to Beach, Village, Restaurants, Bars, Shopping!!

Siesta Key, Florida

SKV 309 - Heated ❤ Pool, Close to Beach, Village, Restaurants, Bars, Shopping!!

🛏 2 bed · 👥 6 guests

Located in Siesta Key, Florida, United States. SKV 309 - Heated ❤ Pool, Close to Beach, Village, Restaurants, Bars, Shopping!! Looking for the ultimate Siesta Key experience? This is it!! Located just South of Morton's in Siesta Key Village. Only 10 min walk to Beach! Heated Pool, Smart TVs w/ Strong WIFI in every room. Comfy beds, fully-stocked kitchen will easily sleep 6. Restaurants, Bars, Seafood, Night Clubs, Big Olaf, Bike rentals, Live Music & so much more -- it's all here. No car needed. Free trolley leaves Morton's every 30 min to take you up and down the Key. You will absolutely love it here!NOTE: BOOKING FEBRUARY? Please book ENTIRE month only NOT mid-month to mid-month. This time frame is a monthly minimum property and we don't want to be empty for part of the time. Booking February 1 - February 28? Okay. Want to book February 15 - March 15? Not okay. Please ask first if you are unsure. We will try and work with you. Thanks in advance.The spaceYour Vacation Home near the HEART of Siesta Key Village!This centrally-locat

$175

/ night

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Location. 3 bedroom cottage block from beach and two blocks from Siesta Village

Siesta Key, Florida

Location. 3 bedroom cottage block from beach and two blocks from Siesta Village

🛏 3 bed · 👥 6 guests

Located in Siesta Key, Florida, United States. Location. 3 bedroom cottage block from beach and two blocks from Siesta Village Location, location, location. Our charming 3-bedroom 2 bath Florida beach cottage, which is over 1000 feet and sleeps 6, which we call the “Manatee Cottage” is across the street from the soft, white sands of the world-famous Siesta Beach which is consistently rated the best beach in the United States (you will be a 5 minute walk from access 7). Enjoy the amazing sunsets each night of your stay without the hassles of traffic, parking and crowds. You will also be 2 blocks from Siesta Village with its numerous restaurants, bars and shops. Park your car and forget about driving as you walk or bike and feel like a local as you enjoy our special piece of heaven.Downtown Sarasota, which is a brief ride or Uber away, is world renowned and known for its cultural institutions, gourmet restaurants, art galleries, theater, the John and Mable Ringling Museum of Art, and the Ringlings’ breathtaking home, Ca’d’Zan on Sar

$328

/ night

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Resort Style Backyard! Private Dock and Beach Views! - Sea Spray

Siesta Key, Florida

Resort Style Backyard! Private Dock and Beach Views! - Sea Spray

🛏 8 bed · 👥 22 guests

Located in Siesta Key, Florida, United States. Resort Style Backyard! Private Dock and Beach Views! - Sea Spray Sea Spray by Siesta Key Luxury Rental PropertiesHome in Siesta Key, FloridaWelcome to Sea Spray! This eight-bedroom and six-and-a-half-bathroom home will check off all the boxes for your desired Siesta Key rental. It is a short walk to Siesta Key Beach and within walking distance to Downtown Siesta Key Village Area. So, catch some sunshine at the beach or enjoy great live music, dining, or shopping in the village. Highlights• Private Dock • Rooftop Deck• Beach Views• Less than a 5-minute walk to the beach• Private Pool with Waterslide and In-ground Spa• Ping Pong• Foosball table• Convenient location near dining and shopping• Dog friendly with approval and additional feeThe spectacular backyard is built like a private waterpark with a Private Resort Style Heated Pool featuring a Rock Water Slide, Waterfall, Grotto, Swim-up bar, Sun Shelf, and Spa. You’ll love the lounge chairs, dining options, and BBQ grill. Just across t

$1,012

/ night

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Full Ocean Views w/Private Beach on Siesta Key, Heated Pool

Siesta Key, Florida

$192/night

Private house, Heated Pool, Pet friendly-walk to beach

Siesta Key, Florida

$194/night

Lovely Rental in Siesta Key Village! Walk to Beach

Siesta Key, Florida

$188/night

Siesta Key Village - Townhouse - Heated Pool - Beach Walkable!

Siesta Key, Florida

$385/night

Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach

Siesta Key, Florida

$404/night

Cabana Cottage Across street from Beach and Heated Pool

Siesta Key, Florida

$272/night

Oceanview Penthouse, in VIllage, 30-steps to Best Beach, Tiki-Bar, Free Bikes and Paddle-boards!

Siesta Key, Florida

$565/night

Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Siesta Key, Florida

$383/night

SIESTA KEY BEACH , ROMANTIC UNIT C

Siesta Key, Florida

$125/night

Kid Friendly Island Home In Paradise!!

Siesta Key, Florida

$274/night

Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Siesta Key, Florida

$306/night

Luxury Pool and Rooftop Deck, Walk to Siesta Key Beach & Village! - Casa Siesta

Siesta Key, Florida

$606/night

Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶

Siesta Key, Florida

$1,239/night

The Little Sandy...#1 in Siesta!

Siesta Key, Florida

$257/night

The Blue Door-Luxury 4BD w/Full Gulf views, private beach access&walk to town!

Siesta Key, Florida

$1,092/night

Heron House | Pet Friendly, Walk to Siesta Key Beach & Village in 2 mins!

Siesta Key, Florida

$437/night

[lounge like locals] walk to siesta beach +bikes

Siesta Key, Florida

$231/night

Siesta Key beach house

Siesta Key, Florida

$342/night

2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

Siesta Key, Florida

$223/night

**Beach, Village, Canal, Dock & Private Heated Pool!!

Siesta Key, Florida

$395/night

Pineapple Paradise | 1 Block from Beach, Community Pool, Resort Style Amenities! ☀️

Siesta Key, Florida

$269/night

SKV 309 - Heated ❤ Pool, Close to Beach, Village, Restaurants, Bars, Shopping!!

Siesta Key, Florida

$175/night

Location. 3 bedroom cottage block from beach and two blocks from Siesta Village

Siesta Key, Florida

$328/night

Resort Style Backyard! Private Dock and Beach Views! - Sea Spray

Siesta Key, Florida

$1,012/night