58,368 properties available

Located in Destin, Florida, United States. Lagoon Pool! Free Beach Shuttle or stroll to dining, shopping & beach! Pool heated & beach shuttle running Thanksgiving, Christmas & New Years!Come, get away from it all and gather your Second Wind.Ideal for 3-4 families with children, or groups of 12-14 adults.Situated in the Villages of Crystal Beach, Second Wind is only a short walk away from one of the most picturesque beaches in the world.  Renewing yourself in the sugar white sands and emerald green waters of the Gulf of Mexico is as easy as a 10-minute stroll. However, if you’re visiting between Memorial Day and Labor Day we invite you to use the free, air-conditioned, beach shuttle service. Simply call to be picked up and dropped off at your doorstep. If paradise by the pool is more your thing then step out the front door of Second Wind and immerse yourself in the luxurious resort style pool. The heated pool features zero-entry access, rock waterfalls, hot tub, tiki hut bar and plenty of lounging areas nestled in a lush, tropi

Located in Siesta Key, Florida, United States. Siesta Beach Retreat Poolside Paradise 2BR Condo Summary:Paradise awaits at our 2BR/2BA beachfront condo at Whispering Sands! With 1282 sqft of space, it offers 2 bedrooms, 2 bathrooms, a private balcony and sleeps 4 guests. Enjoy the convenience of 1 parking space. Located steps from Siesta Beach, this spacious retreat offers a fully equipped kitchen, comfortable bedrooms, and a refreshing community pool. Immerse yourself in Sarasota's vibrant culture, dining, and shopping scene. Your coastal getaway begins here!The Space:Welcome to our spacious 2-bedroom, 2-bathroom condo located at Whispering Sands, Sarasota, FL. With 1282 square feet of living space, this condo offers plenty of room for your comfort and relaxation.The condo features a private balcony, where you can soak up the sunshine or enjoy your morning coffee with a view. Inside, you'll find a well-appointed living area, perfect for unwinding after a day of exploration.The two bedrooms provide ample sleeping arrangements with

Located in Siesta Key, Florida, United States. SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B 100 feet to the beach! Max 4 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, nightlif

Located in Siesta Key, Florida, United States. 15 SS Cottage - Close to Beach and Village Located directly across the street from Siesta Key Beach access 7 and only two blocks to the village! This adorable beach cottage has been newly furnished - island style and has a cozy home feel. There is a private outdoor patio, equipped with table and chairs with umbrella, a brand new gas grill, and a fire pit area to enjoy the evening breezes. Updated kitchen has full size refrigerator, stove, dishwasher and Keurig coffee maker. The Living Room has a full size sleep sofa, LCD TV and wireless internet is provided. The Master bedroom has a King size bed with a LCD TV as well. There is also a stack-able washer/dryer available for your private use! The best feature is the location, directly across the street from the beach, and only 2 blocks to the Siesta Key Village and all it has to offer--Siesta Key Oyster Bar (SKOB), Daiquiri Deck, and of course, the Broken Egg. You can leave your worries and your car behind. One stay and you will never wan

Located in Siesta Key, Florida, United States. Siesta Key Dream Inn Rental - Close to Village! Plan the perfect beach vacation at this Florida vacation rental just steps away from the ocean. This 1-bathroom studio in Siesta Key, Florida, is surrounded by lush landscaping and palm trees to make you feel like you’re in paradise as soon as you arrive. Enjoy a fully equipped interior, shared pool, and provided beach gear so you can pack up and head to the beach whenever you want. Sunshine-loving families and friends can spend the day on the shore followed by an evening in Siesta Key Village!-- THE PROPERTY --Beach Cooler & Towels | Private Balcony | 0.3 Mi to Public BeachStudio: Queen Bed, Queen Sleeper Sofa | Additional Sleeping: Pack ‘n Play 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, 4-person dining tableKITCHEN: Cooking basics, coffee maker, dishwasher, stove/oven, refrigerator, dishware & flatware, ice make

Located in Siesta Key, Florida, United States. Bromeliad | Heated Pool, Games, & More! Centrally Located to Everything in Siesta! 🏝️ Discover Bromeliad - Your Tranquil Retreat Just Moments from Siesta Key Beach!Embark on a journey of serenity at Bromeliad, a tranquil retreat nestled just one block away from the acclaimed Siesta Key Beach, renowned as the #1 beach in the USA. This exquisite vacation rental duplex offers 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:Indulge in the tranquility of Bromeliad, a haven of comfort and coastal charm. Recently renovated, this retreat exudes modern elegance with sleek furnishings and vibrant decor throughout. The fully equipped kitchen beckons culinary adventures, while the sleek bathroom offers a rejuvenating escape. Unwind in the inviting living area or soak up the Florida sunshine at your resort style pool.Guest Access:At Bromeliad, you'll enjoy access to a range of resort-style am

Located in Siesta Key, Florida, United States. Location 1 Bdrm Cottage 1 Block from Beach and 2 Blocks from Siesta Village Location, location, location. Our charming 1 bedroom, 1 bath Florida beach cottage which is over 800 sq. feet and sleeps 2 which we call the "Dolphin Cottage" is across the street from the soft white sand of the world famous Siesta Key Beach which is consistently rated the best beach in the United States (you will be a 5 minutes 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 Key Village, www.escape-to-sarasota.com/siesta-key-village, and 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 Mabel Ringling Museum of Ar

Located in Siesta Key, Florida, United States. Stay IN the Village-2Bed/2Bath - Steps to the Center of the Village!! IN-GROUND POOL This is THE location! Just steps to the Village Cafe and the Hub Bar and Grille, and a short walk to the beach 3.5 Blocks to the Beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed and an auto -inflatable queen size EZ Bed, makes this home comfortable for a family of 8. (**Note: New sofa sleeper and love seat as of July 2022). Granite countertops, stainless steel appliances, fully supplied kitchen and a Keurig machine add to the feel of this house. Master suite with full bath (Updated July 2022 with new shower and floor), large family dining room looking over the canal. Enjoy grilling out, playing a game of corn hole or fish on the canal. Don't forget your furbabies either. This home is extremely pet friendly. NOTE: There is a $250 fee for up to 2 dogs. Must state you are bringing a pet at time of inquiry/booking. An ad

Located in Siesta Key, Florida, United States. Steps From Siesta Key Village And The Powder Sand Of Siesta Key Beach! One of a kind, this special villa is located in the heart of Siesta Key and just steps from Siesta Key Village and a short walk to the powder-soft white sand of Siesta Key. Spacious open floor plan with over 1600 sf plus a private outdoor seating area. Large living area with flat screen tv, separate dining area and Florida room with Mexican tile, cathedral ceilings and windows opening to a private courtyard. Two large bedrooms and two full baths. Kitchen with wood cabinetry and eat in area to enjoy your morning coffee. Attached one car garage with laundry area and extra storage. The feel of your own private home with the convenience of a condo. Complex has a heated pool with plenty of seating. Short stroll to world-famous Siesta Key beach and steps from the Village to enjoy dinner at one of the many restaurants, grab a drink at one of the casual bars, or browse the shops. Great as a getaway to the Key for family

Located in Siesta Key, Florida, United States. Tivoli by the Sea-Unit 404 - Beautiful View of the Gulf 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 4 with a king in the master, and two twin size beds in the guest bedroom. 1 week minimum rental.

Located in Siesta Key, Florida, United States. LuLu's Loggerhead - Walk to Siesta Key Beach, Pool Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a couple of blocks away from famous Siesta Key beach access #5 and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away.With everything you could want and need at your fingertips; We assure you that you will never want to leave Lulu's Key House! We provide everything for your stay! This upstairs 2 bedroom, 2 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 under a café umbrella with a good book while the chef in your family cooks up some bison burgers on the barbecue grill...…medium rare please! This second le

Located in Siesta Key, Florida, United States. 5 walk minutes to one of the best beaches in the US! Welcome to Siesta Key's charming 2-bedroom, 1-bathroom house, nestled amid the serene beauty of this coastal paradise. This delightful abode offers a tranquil escape with its cozy layout and coastal-inspired décor. Step inside to discover an inviting living room filled with natural light, perfect for relaxation or entertaining friends.The kitchen boasts modern amenities and a breakfast bar, making cooking a breeze. Wander outside to the private backyard, where you can unwind on the patio, surrounded by lush greenery and the soothing sound of nearby waves.The two bedrooms are tastefully decorated, providing a comfortable retreat after a day of exploring Siesta Key's sandy beaches and vibrant community. The bathroom features stylish fixtures and a calming ambiance.Located just a short stroll from the world-renowned Siesta Beach, this house offers easy access to sun-kissed shores, breathtaking sunsets, and endless outdoor activities. Wh

Located in Siesta Key, Florida, United States. Living the Dream at this Beautiful 2 Bed/1 Bath Steps from Siesta Key Beach! Experience the Gulf of Mexico breeze 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, 2 twins in the second bedroom, and a queen sleeper sofa in the living room, accommodating up to 6 guests. This unit, located on the ground 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!*No garage parking.Sleeps 6 GuestsBedroom 1: KingBedroom 2: 2 Twin BedsLiving Area: Queen Sofa SleeperIncluded in your stay:Complimentary Bicycles,Wifi,Parking,Beach Chairs,Beach Towels,Beach Wagon,Beach Cooler,Offsite Pool Access,Free

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

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

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

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

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

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).

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

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

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

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

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