58,368 properties available

Located in Siesta Key, Florida, United States. LAST MINUTE! THE BEACH SIESTA KEY VACATION BEST VALUE HOUSE! YOU WILL FEEL LIKE A MILLION DOLLARS. 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. Perfect location between the Village and the main entrance to Siesta Key Beach!! Bar's, Restaurants, Shopping, Sports Siesta key is a beautiful place for weddings, the house is only a 100 feet away from the beach this makes it the perfect location. Rentals……..EVERYTHING is within walking distance…..NO CAR NEEDED!!! 1-minute walking distance from paradise, we are crossing the street to the main entrance siesta key beach the best beach in the United State of America. The neighborhood has lots of restaurants, shopping, and night club with singers and shows in the village. Thi

Located in Siesta Key, Florida, United States. LuLu Kemp Ridley, Walk to Beach, Heated Pool, BBQ Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and night life are steps away. The beach and the crystal clear waters of the Gulf of Mexico is also about a 5 minute walk. You don't need a car. Your vacation destination is here!With everything you could want and need at your fingertips; I assure you that you will never want to leave LuLu's Key House! We provide everything for your stay! This ground level 1 bedroom, 1 bath condo with a heated communal pool (5ft at its deepest) has been completely renovated top to bottom, side to side with nothing left untouched....this home away from home is truly paradise! Come check out this beautifully painted mural in the back pool area where you can relax in the sun poolside or lounge. This tropical oasis h

Located in Siesta Key, Florida, United States. Pineapple | Ping Pong, Heated Pool, Games, & Walk to Beach - Your Dream Vacation! Welcome to Pineapple - Your Tropical Hideaway Just Moments from Siesta Key Beach!Discover the enchanting Pineapple, a serene retreat nestled just one block away from the acclaimed Siesta Key Beach, hailed as the #1 beach in the USA. This exquisite vacation rental duplex the perfect blend of convenience and relaxation, with effortless access to the beach, Siesta Key Village, and an array of resort-style amenities.The Space:Step into this tropical hideaway and immerse yourself in coastal charm. Pineapple boasts a recent renovation, showcasing modern touches with sleek furnishings and vibrant decor throughout. The fully equipped kitchen invites culinary adventures, while the sleek bathroom offers a spa-like escape. Unwind in the cozy living area after a day of exploration or bask in the Florida sunshine at your resort style pool.Guest Access:At Pineapple, you'll enjoy access to a range of resort-style amenit

Located in Siesta Key, Florida, United States. Fern Haven Studio Cottage - walk to Siesta Beach and Village Pets Welcome! SHORT WALK TO THE FAMOUS SIESTA WHITE SAND BEACH & QUAINT ISLAND VILLAGE. Fern Haven is a Key West-style studio efficiency. It is comfy, cozy, bright, and airy with French doors onto a deck overlooking the gardens with festival lights and a brick patio with an outdoor dining area with barbeque. It has a large mirrored doored closet and ample storage drawers under the queen bed. The kitchen has everything you need to make your favorite recipes. Fern Haven cottage is in a quiet and friendly neighborhood with a short walk to the famous Siesta Key beach and village. Across the street, we have a dock where you can launch our kayaks and enjoy the waterways, or rent a boat and dock it there.Pets are welcome with a refundable pet fee.For additional availability on Siesta Key please see our other listings:Blue Lagoon VRBO#1043727 (2B/2B)Canal Place VRBO#1043736 (3B/2B)Garden Terrace VRBO#1043802 (Studio)Tropical Hideawa

Located in Siesta Key, Florida, United States. Cozy Siesta Key Dream Inn Rental < 1/2 Mi to Beach Your next vacation awaits in Siesta Key, Florida! This beachy 1-bath studio is the ideal Florida vacation rental for you and your significant other. Spend your days soaking up the sun on the beach nearby, hanging out by the pool area with a cold drink, or visiting Siesta Key Village where you’ll find shopping, dining, and bars. There’s also plenty to do nearby when you’ve had enough sun, including museums and botanical gardens! You’ll never be bored when you visit this Siesta Key beach rental.-- THE PROPERTY --Sarasota VR Certification: CND6804981 | Beach Cooler & Towels | Shared Heated Pool | 1 Block to Siesta Key Village Studio: Queen Bed, Twin Sleeper Sofa OUTDOOR LIVING (shared w/ 2 other units): Heated pool w/ patio seating, outdoor shower, beach chairs, umbrellas, toys & 2 cartsSTUDIO LIVING: Smart TV, beachy interior, 2-person dining table, patio w/ outdoor seating KITCHEN: Cooking basics, coffee maker, dishwasher, stove/oven, r

Located in Siesta Key, Florida, United States. Oceanside! Large 1BR. In VIllage. 20-steps to Path of Best Beach. Free Bikes and Paddle-boards! “Beachside 603” is a Gertrude Rentals property right on Beach Rd at Access 10. Large, Fully Renovated, 1BR 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. *For larger groups, ask about additional space at this location!603 SIESTA KEY 1BR “AT A GLANCE”- 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 Village's World-Famous Dining & Entertainment. - Alfresco

Located in Siesta Key, Florida, United States. Frangipani | True Florida Getaway! Heated Pool, Themed Room, and Tons of Amenities! Frangipani Retreat: Your Tranquil Haven Just Moments from Siesta Key Beach!Experience serenity at Frangipani Retreat, an idyllic haven 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 tranquility at Frangipani Retreat, a sanctuary 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 bask in the Florida sunshine at your resort style pool.Guest Access:At Frangipani Retreat, you'll enjoy access to a range o

Located in Siesta Key, Florida, United States. Gulf Holiday Unit 11- Updated close to the beach and village! This beautifully renovated, well-appointed one bedroom condo is perfect for a romantic getaway!!. Gulf Holiday is just a short walk to Siesta Key Beach voted #1 beach in the U.S and the Siesta Key Village shops, restaurants, and nightlife. This 2nd floor unit has a newly renovated kitchen with custom cabinets, new appliances, including dishwasher. Bedroom is Newly furnished with a King sized bed with pillow top mattress. New furnishings in living room with a Flat screen TV as well as in the bedroom. Perfect location and size for a beach vacation.

Located in Siesta Key, Florida, United States. Village Breeze III - Heated Pool, Private Patio, Village and Beach! This is The Village Breeze, a Gertrude Rentals property. No car required! Enviable location on quiet street, with heated Pool, ground floor, near Beach, just 250ft to the world famous Siesta Key Village. A true favorite of initiated guests, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. THE VILLAGE BREEZE III “AT A GLANCE” - 2BR/1Bath- Heated Pool & Private Patio.- Steps to Oysters, Craft Beer, Ice Cream, Daiquiris, Live Music, Huge Breakfast, Stone Crab! - Award Winning Beaches, 20 Bar/Restaurants! - Walk to Siesta Key Beaches and clear calm Azure Water & pure quartz White Sand. - Tide Pools & Sand Bars for lounging, sleeping, relaxing, or water sports.- Best Sunsets in North America with 300-degree views of the Gulf. - Kayak, bike, paddleboard, scooter, golf cart rentals. - Free island Trolley & every activity imaginable.- A one of a Kind Island Experience.The Locati

Located in Siesta Key, Florida, United States. Sea Coast | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach! Welcome to Sea Coast, the perfect destination for small families or couples looking for an intimate yet unforgettable vacation experience. Located within the heart of Siesta Key Village and less than 400 feet to the world-renowned Siesta Key Beach, this property offers the ultimate combination of convenience and coastal charm.Sea Coast is a 1 bedroom 1 bathroom recently renovated private unit designed to accommodate your vacation needs, whether you're traveling solo, as a couple, or with a small group. Whether you choose to rent the entire property or individual units in the duplex, you'll have plenty of space to relax and unwind. This unit can comfortably accommodate up to 4 guests, featuring 1 king bed and 1 modular sleeper sofa, equipped with high-quality linens. Sea Coast is thoughtfully designed and newly furnished, creating a fresh and inviting atmosphere that feels like a home away from home.For

Located in Siesta Key, Florida, United States. Walk to the beach - Island Villa Escape to Paradise in Siesta Key VillageIntroducing Hibiscus Villa – the perfect tropical retreat in the heart of Siesta Key! This spacious one-bedroom villa is just steps from the shops and restaurants of lively Siesta Village and only a three-minute stroll from the world-famous white sands of Siesta Key Beach.Siesta Village is a charming coastal community with plenty to see and do. Stroll down Ocean Boulevard and take your pick from over 20 restaurants ranging from beach bars to fine dining. Shop at dozens of boutiques for the perfect souvenir. Enjoy local entertainment and live music at various venues. And make sure to catch the Sunday sunset drum circle on the beach!The villa's ideally located complex features a heated pool and lush landscaping for lounging alongside your family and friends. We provide everything you need for adventure, including a beach wagon stocked with chairs, and towels.Inside, 900 square feet of coastal comfort await. The full

Located in Siesta Key, Florida, United States. Gulf Front Siesta Key Beach Condo Salt Life Villa is a ground-floor 2 bedroom/2 bathroom condo featuring full panoramic Gulf of Mexico views from the living room & the master bedroom. Your dedicated covered parking space is just 8 steps to your front door, with no stairs to climb! Step through the front door to the open floorplan featuring a living/dining area with bar, Smart TV, private high-speed WiFi, & full view sliding doors leading to the lanai. The kitchen is upgraded with all the amenities of home. Two well-appointed bedrooms with fully private ensuite bathrooms, TV/DVD players, & ceiling fans for comfort. A private washer/dryer is also a nice amenity- no sharing with other guests!The beachside, fully furnished screened lanai offers a "walk right out the door" down our private beach path to the pristine Gulf waters and powdery white sugar sand of the world renowned and #1 rated Siesta Key Beach. There is also a smaller side patio accessed only from the master bedroom with an o

Located in Siesta Key, Florida, United States. A Beautiful 2 Bed/1 Bath for Living the Dream Steps from Siesta Key Beach! Experience the Gulf of Mexico breeze and partial gulf views with this lovely 2-bedrom, 1-bathroom home directly across from our world-famous Siesta Key Beach! Beautifully decorated, this home features a king bed in the master, a queen in the second bedroom, and a queen sleeper sofa in the living room, accommodating up to 6 guests. This unit, located on the second floor, is right outside of the Siesta Key Village, making it a breeze to walk to many of the restaurants, shops, and live entertainment the island has to offer. Relax in the sugary white sand or swim in the crystal-clear waters. Enjoy the brilliant colors of sunset at this beautiful vacation home that will have you coming back year after year!*Stairs only. All guests must have the ability to climb stairs.*No garage parking.Sleeps 6 GuestsBedroom 1: KingBedroom 2: QueenLiving Area: Queen Sofa SleeperIncluded in your stay:Complimentary Bicycles,Wifi,Parki

Located in Siesta Key, Florida, United States. Siesta Village Short Walk to Beach w heated Pool Summary:Located a block off Siesta Key Village, this quaint single level ground entry condo awaits you. No need for car rental with all the Keys favorite bars, restaurants within walking distance but also includes 2 parking spots. Community heated pool for those afternoon dips after returning from the top rated beach in the USA (8 min walk) or Hop on free trolley to explore the Key. Minutes from downtown Sarasota, small dog friendly, wifi, smart tv, in unit W/D and basic home & beach gear provided.The Neighborhood:Calle Mingora - Heart of Siesta Village

Located in Siesta Key, Florida, United States. Sea la Vie | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining Welcome to Sea la Vie, a coastal villa that offers the perfect blend of luxury, convenience, and relaxation. This remarkable duplex property can be rented separately or as a whole, known as Siesta Sea Life, allowing you to choose the ideal accommodation to suit your needs. With a shared heated pool, an unbeatable location just a 3-minute walk from Siesta Key Village, and a mere 1-minute walk to the pristine Siesta Key Beach, Sea la Vie is your ultimate gateway to an unforgettable vacation.Featuring 3 bedrooms and 2 full baths, including 1 master bedroom, Sea la Vie provides ample space to comfortably accommodate up to 8 guests. The sleeping arrangements consist of 1 king bed and 3 queen beds, all equipped with high-quality linens to ensure a restful night's sleep.To ensure a seamless start to your vacation, we provide a starter pack of toiletry essentials, including shampoo, conditioner, hand/fa

Located in Siesta Key, Florida, United States. Private Patio, Bright-Airy, Newly Remodeled. Steps to Best Beach, Village Shopping & Dining! This is "Siesta-Zen", a Gertrude Rentals property. Leave the car behind! Beautifully decorated, set on a private street just 450 steps to best beach on the Siesta Key and five minutes walk to Siesta Key Village! Sure to provide a combination of fun, ease and relaxation you can't get in other properties.THE SIESTA-ZEN 2BR “AT A GLANCE”- Beautifully Remodeled, Modern, and Peaceful.- 450 ft to Siestas Best Beach access, 4-minute walk to Village's World-Famous Dining & Entertainment. - Private Patio Garden, & Alfresco Dining table. - Award Winning Beaches, 20 Bar Restaurants, Walk to everything!- Clear calm Azure Water & pure quartz White Sand. - Tide Pools & Sand Bars for lounging, sleeping, relaxing, or water sports.- Best Sunsets in North America with 300-degree views of the Gulf. - 20 Restaurant-Bars, Live Music, Daiquiris, Oysters, stone crab, ice cream, fresh donuts.- Kayak, bike, p

Located in Siesta Key, Florida, United States. Beautiful 5 Bedroom Home Directly on Siesta Key Beach!! DIRECTLY ON #1 BEACH, SIESTA BEACHExperience the breathtaking views of this beachfront home! Located directly on Sunset Beach on Siesta Key, this 5-bedroom 4-bathroom home is a must. Inside, this home is beautifully decorated and can comfortably sleep up to 14 guests. This home comes equipped with a full kitchen, a dining area, and a spacious living room for you to enjoy time with your family and friends. Watch the spectacular sunsets from one of your multiple balconies located on each floor, or walk out your front door to the sugary white sand of our world-famous beaches. This unit also includes a very convenient outdoor shower and the use of the pool at the Siesta Key Beachside Villas just a block away. Even better still, this unit is only a short stroll into Siesta Key Village, where you can experience many of the wonderful shops and restaurants the island has to offer! With views like this, this vacation home is sure to be you

Located in Siesta Key, Florida, United States. Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West Island Time West by Siesta Key Luxury Rental PropertiesHome in Sarasota, FL 34242Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key!Welcome to Island Time West, a beautiful vacation home just minutes away from the amazing Gulf of Mexico beaches and Siesta Key Village, where you can explore a variety of restaurants and shops! This getaway boasts three bedrooms and three and a half bathrooms. You'll love the game room with a Ping Pong and Foosball table and the lovely backyard with a sparkling pool and in-ground spa! At A Glance• Less than a 5-minute walk to the beach• Private Pool and In-Ground Spa• Game Room• Dog Friendly• Covered PatioThe kitchen has stainless steel appliances and enough seating for guests to spread out comfortably, including a rustic-style table and bar seating. Outside, on the covered patio by the pool, you'll find a picnic-style table, a b

Located in Siesta Key, Florida, United States. Lower Prices! Walk to Village, Heated Saltwater Pool Welcome to the Blue Mermaid on Siesta Key!! This gorgeous custom home is located less then 1/2 mile and less than a 10 minute stroll from Siesta Key Village. Only a 12 minute walk/bike to the beach with crystal sands and sparkling warm waters of the Gulf of Mexico. Walk to our local gourmet grocery store for freshly prepared sushi, or for a morning freshly prepared donut and coffee, organic gelato, the Hub Baja Grill for live music and freshly prepared lobster tacos and so much more.........Bring your bike or rent one here as it is only a short bike ride to Siesta Key public beach! The beautiful custom newer home has a heated saltwater pool with an outdoor shower and everything you need for a fantastic and memorable vacation! You will want to come back again and again!Quick Highlights:Master: King Bed, Smart TVGuest 1: Queen bedGuest 2: Queen bedUpstairs Alcove: Sofa Bed for 1 (sleeper mechanism not functional but can use the

Located in Siesta Key, Florida, United States. King Bed - Private House - Walk to Village & Beach - Heated Pool/Spa - No Stairs Spend the day at the beach, swim and relax in the hot tub and or heated pool, rent a boat and dock right behind the home, walk to the local restaurants, this home has it all. The Master bedroom has a king bed, dresser, and a double sink bathroom. Our garage is full of bikes for visitors, including a pull-behind cart and provided beach gear. Tons of beach chairs and toys for all ages stocked or left behind for others to enjoy.Stainless Weber grill and a well-stocked kitchen.I have a property maintenance contact who can assist with any issues less than 1/10 mile away, so relax and enjoy.

Located in Siesta Key, Florida, United States. Siesta Key Village and Beach Walkable, Condo, Private Porch 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 Siesta Key Dream’s vacation rental features a bright, welcoming 1 bedroom, 1 bath space. You’ll experience an open floor plan connecting a welcoming living room and kitchen with a stove, fridge, & microwave. In a separate room, you’ll see your comfortable queen bed and a private bathroom. Siesta Key Dreams is happy to provide free, high-speed internet & Wi-Fi, an HD Television equipped with live sports & extension channel options via free streaming servi

Located in Siesta Key, Florida, United States. Tropical Oasis | Luxury Home on Siesta Key w/ Private Heated Pool/ Spa, Steps to Beach & Village! Welcome to Tropical Oasis. This private family home is perfect for large families, with the ability to accommodate up to 16 guests, with 7 bedrooms and 6.5 bathrooms.The backyard is a twinkling mirage, secluded by rows of palms that will have you feeling like you're thousands of miles away in a tropical resort. The private, heated pool and spa create an oasis of sparkling water, while the pristine putting green and ping pong table ensure hours of entertainment without stepping a foot off the property. Use the stairs or take the private elevator to reach the second floor with a luxurious lounging area, affixed with an array of bedrooms. Twin bunk beds, a jack and jill bathroom, along with queen and king bedrooms with ensuites create an entire floor with a myriad of sleeping arrangements that will create a comfortable night's sleep for every guest. A luxe wet bar is nestled next to the floor

Located in Siesta Key, Florida, United States. The Wildflower | Reserve Your Private Resort with Pool, Games, 1 Block to Beach! 🏝️ Discover Your Private Oasis at Wildflower: A Resort-Style Retreat Just Moments from Siesta Key Beach!Indulge in luxury and exclusivity at Wildflower, an enchanting resort-style retreat nestled just moments away from the pristine shores of Siesta Key Beach. With its lush surroundings and array of upscale amenities, Wildflower offers the perfect setting for a memorable vacation experience.The Space:Welcome to Wildflower, your own private oasis where luxury meets tranquility. This sprawling resort boasts eight separate units, each meticulously designed and furnished to ensure maximum comfort and relaxation. From spacious living areas to fully equipped kitchens, every aspect of Wildflower has been crafted with your ultimate enjoyment in mind.Guest Access:As a guest at Wildflower, you'll enjoy exclusive access to a wealth of resort-style amenities. Take a refreshing dip in the sparkling pool, unwind in the s

Located in Siesta Key, Florida, United States. Luxury Condo - Ocean Views & Rare Rooftop Sundeck 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.Offering some of the best views of Siesta Key Dream’s portfolio and PRIVATE beach access with a gated key, this location features a crisp and airy 3 bed, 2 bath layout. This rental is perfect for family and friend gatherings and can accommodate up to 10 guests (8 adults and 2 children) with a total of 7 beds. This large, spacious floor plan connects a welcoming living room, a dining room that can accommodate well more than 8, and a full kitchen. Next to your living room