72,107 properties available

Located in Siesta Key, Florida, United States. Tropical Paradise 3 Bed 3 Bath House Make some memories at this unique and family-friendly place. Enjoy this lush and tropical pool area that will almost make you forget that a highly rated sometimes rated #1 Beach is just steps away! Provided for you are all the necessary beach items like beach towels and chairs and more! If you are looking for a little more space there is also a 1 bedroom 1 bath Cottage right next door that can be rented as well. Please inquire to see if we have both open at the same time.

Located in Siesta Key, Florida, United States. Beautiful, Spectacular view on the Ocean, new furniture, oversized deck/balcony Check out my other amazing VRBO property reviews: Vrbo.com/4802815 ! Location, location, location! This beautiful apartment has been decorated to a home cozy feel. Newly done oversize balcony has most spectacular view on the Gulf and Beach, so you can enjoy watching sun rays shining on the water while having a romantic dinner. Just 3 min. walking distance to the beach and 3 min walking distance to the center of Siesta Village, with all restaurants, bars, live music , shopping, biking and more.This very spacious 3 bedroom apartment was renovated for our guests with every thought of detail for what you might need while you stay with us. New furniture, fresh paint, new fresh sheets and towels. Fully supplied kitchen.We just finished renovating downstairs huge decking and entire landscaping. It is great place to invite some of your friends as this area is for use of our tenants only.We get 100% satisfaction f

Located in Siesta Key, Florida, United States. SKV 311 - Heated ❤ Pool, Walk to Village, Beach, Bars, Restaurants !! 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.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!The spaceYour Vacation Home near the HEART of Siesta Key Village!This centrally-located & Cozy

Located in Siesta Key, Florida, United States. Private Pool and Spa near the Beach! - The Jasmine House The Jasmine House by Tropical Sands Accommodations Home in Sarasota, FL 34242 Welcome to The Jasmine House! A stunning three-bedroom, three-bath vacation home just minutes from Siesta Key Beach and Siesta Key Village. With an inviting backyard oasis and proximity to local hotspots, it promises an unforgettable getaway. Highlights • Less than a 10-minute walk to the beach • Private pool with in-ground spa • Outdoor living space • BBQ grill • Near restaurants and shops Discover a warm, welcoming interior featuring two well-appointed seating areas with a large smart TV, and a modern dining room table. The kitchen has stainless steel appliances, a generous center island, and a convenient pass-through window to the dining room, complemented by a handy wine fridge. Catch some ZZZ's in the first and second bedrooms, both adorned with high-end furnishings and sumptuous king beds dressed in soft bedding. Enjoy the convenience of ensuite

Located in Siesta Key, Florida, United States. Private Pool! Walk to Siesta Key Beach & Village! Take a break and unwind at this peaceful, ranch style home on Siesta Key. With 3 king beds and 2 large couches, you and your family will have room to enjoy rest and relaxation poolside or take a short, 2 block walk to USA's #1 Beach. Enjoy dinner and drinks without worrying about needing a ride home from the Village, or catch a trolley down to Stickney point and enjoy a meal without leaving the Key.KEY AMENITIES / DETAILS:✓ Check-out process: Chore-Free Checkout®✓ Check-in process: Keyless entry with code✓ Check-in technology: Dack-enabled, swipe to unlock, digital guide ✓ 3 Bedroom end unit row house with private entrance✓ 2.5 bathrooms✓ Sleeps 8 in two king and two queen beds✓ Pool: Completely private✓ Internet: High speed 300mbps✓ Work from Home: Desk✓ Parking: Free driveway parking✓ Laundry: HE Washer/dryer✓ Kitchen: Fully stocked with quality amenities✓ Tech: G-Mini enabled speaker, Smart TVs ✓ Eco-friendly: Recycling, earth-friend

Located in Siesta Key, Florida, United States. Admirals Watch | Ocean View w/ Spacious Balcony, Heated Pool, & Walking Distance to Siesta Key Beach Imagine waking up to the gentle sound of waves crashing against the shore, and looking out to see the shimmering turquoise waters of the Gulf of Mexico just steps away from your luxury vacation rental home. This stunning 3 bedroom 3 bathroom condo is situated directly across the street from Siesta Key Beach, one of the most beautiful beaches in the world.The focal point of Admiral's Watch is its breathtaking views. The balconies provide the perfect spot to sit and relax with a glass of wine, while you watch the sky change colors. This property's elegant decor and high ceilings make it feel open and spacious, while the private elevator provides easy access to all levels of the property. The kitchen and dining area reveal stunning water views and provide the perfect spot for intimate family meals.The semi-private heated pool and outdoor lounging area provide a perfect place to cool off fr

Located in Siesta Key, Florida, United States. Tivoli by the Sea-Unit 604 - Beautiful view and sleeps 6 Your Ultimate Vacation Getaway Awaits you here @ Tivoli by the Sea! Absolutely gorgeous and newly renovated 2 bedroom/2 bath unit sits on the 6th floor, with amazing views of the Gulf of Mexico. Sit on your 26ft balcony and watch our spectacular sunsets! Sit on your 26 ft open balcony & watch our spectacular sunsets! This unit sleeps 6 with a king in the master bedroom, a queen and twin trundle bed in the guest bedroom. 1 week minimum rental

Located in Siesta Key, Florida, United States. Stunning 3 Bedroom Townhome With Rooftop Sun Deck Steps From Siesta Key Beach! Welcome to Surfside Swank! Where you will experience beautiful Siesta Key Living! This 3-Bedroom, 2.5-bathroom home sleeps up to 6. Relax on the spacious rooftop sun deck and take in the amazing sweeping views of our world-famous beach, Siesta Key. Inside, on the first living level, you will find a large, open living area, a half bathroom, a nice sized balcony for enjoying that island breeze, and a large kitchen with plenty of space to cook in. The second living level has 3 bedrooms, 2 full baths, a washer and dryer, and another balcony off the bedrooms. Up one more flight of stairs is the large rooftop sun deck, perfect for watching gorgeous sunsets all year round. This home is equipped with 2 parking spaces: 1 in the drive way and 1 carport space is in the rear. For your convenience, there is an onsite beach access path that will lead you to the sugary sands and crystal-clear waters. This home is just a sh

Located in Siesta Key, Florida, United States. Ocean view townhouse/First line on the beach! Wake up to gorgeous Ocean and beach view and enjoy breathtaking private sunsets every evening ! First line on famous white powder sanded beach of Siesta Key with unobstructed views! Three story townhouse, located in hearth of the Island, close to Siesta Key Village with all restaurants, shops and bars. 2 large verandas with comfortable sitting and dining sets and patio on first floor with outside kitchen and grill; 3 office desks, open floor plan, lots of space. sleeps maximum 4 adults and 2 children.Hearth of Siesta Key Island, small community of 8 units, sharing the driveway and deeded access to the beach. Quiet.

Located in Siesta Key, Florida, United States. Vintage Cottage from 1936 across street from Beach and Heated Pool Immerse yourself in historic Florida beach life with this one-of-a-kind accommodation! No other hotel or resort room can come close to the old Florida charm of The Cottage.Built in 1936, The Cottage graces the front portion of 515 Beach Rd. A lovely 20 x 20 screened in porch is the entryway to this fabulous Vintage Florida Beach House. As you walk through the two French glass doors, you are greeted by original pine wood floors, vaulted ceiling, pecky cypress paneling. The focal point in the living/great room area is a beautiful natural stone fireplace. The mantelpiece now hosts a 65 flat screen TV with Blu-ray player. The Master bedroom hosts a King size Bed which is a Serta ICOMFORT Memory Foam Gel bed. This bedroom has its own private walk in shower enclosure bath attached. There is also a flat screen TV in the master bedroom for your convenience. The second bedroom consists of two Queen Serta ICOMFORT Memory Foam G

Located in Siesta Key, Florida, United States. Private Gated Home in Siesta Village, Heated Pool & Pool Table - The Hideaway The Hideaway by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Welcome to The Hideaway, a luxurious private gated home with four spacious bedrooms and four and a half baths. This home's stunning custom design and top-notch amenities will awe you and your guests. The screened-in pool patio will undoubtedly become your favorite spot to unwind and relax, whether you want to take a dip, lounge on the comfortable sunbeds, or whip up a delicious BBQ feast. The possibilities are endless at The Hideaway! Highlights• Less than a 5-minute walk to the beach• Private pool• Screened-in patio• High-end kitchen appliances• Pool table• Elevator• BalconyThis contemporary home has an open layout that connects the living room, dining area, laundry room, half bath, and kitchen. The gourmet kitchen features a g

Located in Siesta Key, Florida, United States. Beach Access and Balcony with Views of the Gulf - Tivoli by the Sea-Unit 405 Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen and a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets!! This unit sleeps 4, with a king in the primary and a queen bed and twin bunk bed in the guest bedroom. Private beach access. 1 week minimum rental.

Located in Siesta Key, Florida, United States. NEW: Steps to the BEACH! Lovely Beach House with a screened-in saltwater pool Only steps to the BEACH! Spacious and enchanting 3 bedroom/2 full baths ground-level property (sqft 1,322) offers 1 King, 1 Queen and 2 Twin beds. The Beach House features central A/C, a lanai, a full modern kitchen with stainless-steel appliances, a dishwasher, front-loading washer/dryer, and a saltwater pool! Pool is shared with the Beach Cottage on the same property. It also offers complimentary Wi-Fi, a 50” flat scree satellite TV in the living room and a 32” flat screen TV with Netflix in one bedroom.

Located in Siesta Key, Florida, United States. Beach Road Condo - Private Decks - Siesta Key Beach & Village Walkability! 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.One of the closest rentals to the beach in Siesta Key Dream’s portfolio features a total of 3 bedrooms and 3 bathrooms. This rental is a 2-bedroom and a studio-suite that combine to become a perfect arrangement for family and friend gatherings. Collectively the unites can accommodate up to 9 guests. The entrance for both are on the same deck, with one door going into the second floor 2-bedroom condo, and the other door opening to a flight of st

Located in Siesta Key, Florida, United States. Stunning 3 Bedroom Steps from Siesta Key Beach Access! Spend your vacation relaxing in this lovely 3-bedroom, 2.5-bathroom townhome. On the ground level, you will find parking for up to 2 cars, storage, and a beach bath. The second level hosts a spacious living room, dining, and kitchen areas. The kitchen offers plenty of storage and stainless countertops. The living room offers space for the entire family to relax with large windows looking out towards the beach. On this floor, you will also find a powder room and the first of two balconies for enjoying the fresh island breeze and ocean view. The 3 bedrooms, 2 full bathrooms, and second balcony are located on the third level. Located within walking distance to Siesta Key Village, this home is adjacent to beach access #10 – perfect for taking a trip down to Siesta Beach or enjoying a stunning view! *This property is stairs only; all guests must have the ability to use stairs.Bedroom 1 – KingBedroom 2 – Twin over Queen Bunk BedBedroom 3

Located in Siesta Key, Florida, United States. Beachfront Luxury, Direct Beach Access, Gulf Views, Resort Style Pool w/ Spa Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation experience!Unlike most vacation rental companies, Vunique Vacations offers any day arrivals for most of the year and stays starting at 3+ nights depending on local ordinances. If the travel dates you are looking for don’t appear to be available, please contact our reservations team directly and we will see if we can accommodate your request at your property of choice, or another comparable home in our portfolio.Beachfront Luxury Vacation Rental! Sunset Blue is the best Beachfront Property on Siesta Key! This luxury rental home on Siesta Key is set up for a premier vacation experience! It is one of the best luxury vacation rentals available in Florida, and certainly the best in Siesta Key! With unmatched Gulf and Beach views from the approximately 4,200 square feet of interior living space and

Located in Siesta Key, Florida, United States. Siesta Key Beach House Just Steps To Beach And Village - Location - 1 block to Siesta Key's Public Beach and in about 0.5 miles to Siesta Key downtown / Village.This bright and amazing 3 bedroom / 3 baths pool home offers an open floor plan. The saltwater pool is surrounded by a screened-in lanai. This home also has beautiful Plantation shutters, bamboo flooring and updated amenities. It comes with a queen bedroom & a full bath ( walk-in shower & grab bars.) Twin bedroom with a full bath (walk-in shower) and the master bedroom, king bed, full bath (tub & grab bars) and a double vanity. The spacious eat-in kitchen is fully equipped and great for family entertaining's. A gas grill is available and guests are responsible to replace gas tank if its empty. Property is completely fenced in for privacy. Other things to note**No parties**No smoking indoors**No pets**No glass by the pool**Please respect the home & neighborsWhen booking PLEASE provide your email info and cell phone number o

Located in Siesta Key, Florida, United States. Beach Rd Studio - Ocean View - Deck - Siesta Key Village & 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.One of the closest rentals to the beach in Siesta Key Dream’s portfolio features a bright, airy studio space on the third floor of the building. Your comfortable, queen sized bed overlooks a private balcony providing partial beach views, perfect for your morning coffee. You’ll experience an open floor plan connecting a welcoming living room, bed, and kitchen with an island, stove, fridge, & microwave. Siesta Key Dreams is happy to provide free,

Located in Siesta Key, Florida, United States. One-of-a-Kind! Pool, Terraces, Ocean-View Rooftop, in Siesta Village at Best Beach! Las Ventanas, Siesta Key, you deserve this! A one-of-a-kind Resort like setting in the heart of Siesta Village, just 450ft to Siesta's best Beach. Spacious, bright, airy, and surrounded by palms with a terrace off every bedroom. Private amenities include an Ocean View Rooftop Deck with wet-bar, Elevator, Pool-side Lanai, 3 Terraces, and a fully appointed Swim-out Room. Shared amenities are a Heated Pool with 2 Sun-Shelves. Swim-out Room has a bath, wet-bar, living area, TV and ping pong. All of this is highlighted by 3000 ft.² of windows and views of Royal Palm's. *Las Ventanas is now a Gertrude Rentals property!LAS VENTANAS “AT A GLANCE” - Large 4BR/5Bath unit (sleeps up to 13)- Oceanview rooftop deck and 3 Balconies.- Heated Pool (shared) and sun-shelves with private Lanai.- 450ft to award Winning Beaches, 25 Bar-Restaurants.- 100% private rooftop deck with views of the best sunsets in north

Located in Siesta Key, Florida, United States. 400 yards to Siesta Key Village, 800 yard To The public Beach Access 2 and 7. ONE OF A KIND PROPERTY four blocks from SIESTA KEY Beach so,pack up your cooler, and all your beach supplies, and take the short walk(400 yards directly on to the #1 Rated Beach in America! (we supply bikes, umbrellas, chair, cooler and paddle board)After you make some memories at the beach, walk 200 yards down to Siesta Key Village and grab a bite to eat, a drink, or catch some live entertainment from one of the many talented musicians playing at numerous locations. This property comfortably sleeps 8 people with a three bedroom, three bathroom, an office that can be use as bedroom and two large couches.Two garage plus a lot parking space, WIFI,, cable and a patio with a Jacuzzi, that fits eight people. Kick off your shoes and relax because with this rental you get the best of everything!!

Located in Siesta Key, Florida, United States. Tivoli by the Sea-Unit 505 - Gorgeous View Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen & a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets!!! This unit sleeps 5 with a king in the master, a full and twin bed in the guest bedroom. 1 week minimum rental.

Located in Siesta Key, Florida, United States. Coral Cottage Beach house with heated pool with boat dock Coral Cottage is a luxurious newly furnished 4 bedroom, 3 bath townhome in the heart of Siesta Key. Perfect location to walk 1 block to the beach or to world famous Siesta Village! Our townhome has all the upgrades. Start your day by enjoying your morning coffee on one of the many balconies after being prepared in our fully stocked chefs kitchen. End your day relaxing by the heated pool overlooking your private boat dock on the Canal. With all the extras you could want, Kayaks, paddle boards, and bikes to get around the island. Walk to the world famous Siesta Village and enjoy fine dining combined with beach themed bars and amazing entertainment. Shopping at its finest in this resort village from souvenirs to nick knacks. A centrally located home 40 to 60 minute drive to Bush Gardens and Lego World, Ice Skating Rink and Museums. This home will make your vacation one that will be remembered.World famous Siesta Key provides an ex

Located in Siesta Key, Florida, United States. Beach Walk Cottage | Pet Friendly Home on Palm Island, Private Pool, Ping Pong Table, Walk to Beach! Embark on a rejuvenating getaway to Beach Walk Cottage, a charming coastal haven nestled in the heart of Siesta Key. This quaint home offers a perfect blend of comfort, convenience, and coastal charm, ensuring an unforgettable vacation for you and your loved ones.This home offers 3 cozy bedrooms and 3 full bathrooms, including 2 master bedrooms. The bedrooms feature a comfortable king bed, a queen bed, a bunk bed with a full and twin bed, and an additional twin bed, accommodating up to 8 guests. Linens are provided for your convenience, ensuring a restful night's sleep.Just a short 5-minute walk away, Siesta Key Beach invites you to explore it's expansive shoreline and take in the beauty of The Gulf of Mexico. Spend leisurely days sunbathing, building sandcastles, or taking tranquil walks along the emerald water. The convenience of being within easy reach of this world-renowned beach ad

Located in Siesta Key, Florida, United States. Lantana | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach! Welcome to Lantana – Your Tranquil Retreat in the Heart of Siesta Key VillageDiscover Lantana, a charming getaway nestled in the lively heart of Siesta Key Village. This unique vacation rental duplex offers two bedrooms and two full bathrooms, making it the perfect choice for small families or groups seeking a relaxing escape.Pet-Friendly & Perfectly Located: Lantana is pet-friendly, so bring your furry friends along for the adventure! (Please confirm pet availability when booking.) Situated just a three-minute stroll from the world-renowned Siesta Key Beach, you'll enjoy easy access to the vibrant energy of the area, from its powdery white sands to its breathtaking sunsets.Relaxing Poolside Retreat: After a day of exploring, unwind by the heated pool or relax in the comfortable lounging area. The screened-in lanai provides a shaded spot where you can enjoy the warmth of Florida without direct sun,