15 Fabulous Siesta Key Vacation Rentals for Your Florida Beach Getaway

Home to the best beach in the United States, Siesta Key is ideal for a beach vacation for the whole family. Not only does it feature powdery white sand beaches made of quartz, this gulf-side barrier island also offers everything from kayaking and boating to daytime dining and drinking. Spend the day shelling, then savor a succulent crab as you watch the stellar sunset. This island paradise is not a well-kept secret, so finding a good place to stay can be difficult. That’s why we painstakingly combed through Siesta Key Vrbo listings to find the perfect vacation rental for your Florida beach getaway.

Whether you want to stay in the heart of Siesta Key Villagewith its variety of casual restaurants, tropical bars and live entertainment, or if you prefer to stay further off the beaten track, we’ve found some fabulous Siesta Key vacation rentals for your stay in the Sunshine State.

  1. Bayside Condo

  2. This first floor condo is part of the Gulf & Bay Club Bayside gated community on the Florida side of Siesta Key. The accommodation has a closed terrace which overlooks a pond. Community facilities include two heated swimming pools, two tennis courts, a fishing pier and a clubhouse with a dry sauna and gym. Enjoy access to the large private beach, which is just a five minute walk across the street. Beach chairs, toys, towels, an umbrella and a cart are provided. Parking is also provided in the attached garage.

    Bedrooms: 2

    Bathrooms : 2

    Sleeping: 6

    Minimum night: Varied

    Rent now

  3. Crescent Arms Condo

  4. Crescent Arms Condo

    This two bedroom condo is nestled in the gated community of Crescent Arms, which sits on the Gulf of Mexico just north of the Stickney Point Bridge. The sugar-white sands of Crescent Beach can be seen from its enclosed veranda.

    Bedrooms: 2

    Bathrooms : 2

    Sleeping: 6

    Minimum night: 7

    Rent now

  5. Siesta Key Village Tiki Apartment

  6. Siesta Key Village Tiki Apartment

    This centrally located condo is just one block from Siesta Key Village and the beach is also within walking distance. Its fun and colorful pool includes tiki bars. This pet-friendly place is perfect for people who want to bring their pup.

    Bedrooms: 2

    Bathrooms : 2

    Sleeping: 4

    Minimum night: Varied

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  7. Siesta Key Village Apartment

  8. Siesta Key Village Apartment

    Nestled in the heart of Siesta Key Village, one block from Ocean Boulevard, this two bedroom apartment is part of the Village West complex. Community amenities include a heated swimming pool and a reserved parking space. The beach is just a minute walk away. You don’t even need to bring beach chairs, they are already waiting for you at the beach! A beach cart and cooler are provided. Take the free cart or one of the “tip only” golf cart shuttles to experience upscale restaurants, shopping and nightlife in the village.

    Bedrooms: 2

    Bathrooms : 2

    Sleeping: 8

    Minimum night: Varied

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  9. House On Grand Canal With Swimming Pool

  10. House On Grand Canal With Swimming Pool

    Located on the Grand Canal, this four-bedroom vacation rental is on a quiet street in a very pleasant neighborhood. Spend your time lounging by the secluded private pool or take a short walk to the beach. Several bikes, a few beach chairs, umbrellas, a cooler, plenty of beach toys, and plenty of beach towels are provided. Siesta Key Village is minutes away.

    Bedrooms: 4

    Bathrooms : 3.5

    Sleeping: 8

    Minimum night: 14

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  11. Canal house with swimming pool

  12. Canal house with swimming pool

    Located along the canal in a quiet, upscale neighborhood, this four-bedroom vacation rental features a private splash pool in an enclosed veranda. Plenty of parking spaces are provided in the garage and driveway. There is also a private area to launch a kayak. Siesta Key beach is within walking distance and the village of Siesta Key is approximately a 15 minute walk away.

    Bedrooms: 4

    Bathrooms : 3.5

    Sleeping: 8

    Minimum night: Varied

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  13. The beautiful siesta

  14. The beautiful siesta

    Nestled among century-old oak trees, this three-bedroom vacation rental sits across from a private school in a safe and quiet neighborhood. This peaceful retreat features a heated saltwater pool in a screened-in patio. The village of Siesta Key is within walking distance. Note: Home can only be rented once per 30 days due to zoning restrictions.

    Bedrooms: 3

    Bathrooms : 2

    Sleeping: 8

    Minimum night: 7

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  15. Beach House With Pool

  16. Beach House With Pool

    We don’t know which is better, the fact that this house has a private pool and jacuzzi, whether it is located on the Grand Canal or two blocks from the famous beaches of white sands of Siesta Key. Oh, and it’s walking distance to Siesta Key Village!

    Rent a boat or a jet ski and shoot to the back of this dream vacation home. It also offers easy access to beautiful areas for walking, running or biking. Take in views of the pool and the Grand Canal from two of its three balconies. Plenty of parking spaces are also available.

    Bedrooms: 3

    Bathrooms : 3

    Sleeping: 8

    Minimum night: Varied

    Rent now

  17. Casa De Siesta

  18. Casa De Siesta

    Casa De Siesta is perfect for a pair of families traveling together as it is a combination of two units that can accommodate a total of 12 people. A dog up to 25 pounds is also allowed for a fee. Out back there’s everything your group needs to have fun in the South Florida sun, including a pool, hot tub, outdoor dining table, grill and lounge chairs . The rental also includes everything you’ll need for a day at the beach: a cooler, beach towels, a cart and beach chairs, which is good because the beach is steps away. The village of Siesta Key is also within walking distance.

    Bedrooms: 4

    Bathrooms : 3

    Sleeping: 12

    Minimum night: Varied

    Rent now

  19. Sun Castle

  20. Sun Castle

    Just a block and a half from the powdery white sands and turquoise Gulf of Mexico waters of Siesta Key Beach, this spacious four-bedroom home sleeps 11. From the master bedroom, a balcony offers a partial ocean view – the perfect place to sip a margarita and watch the sun set over the water. Relax by the heated saltwater pool with waterfall. An outdoor shower makes it easy to rinse off the beach. Plus, Siesta Key Village is just a few blocks away.

    Bedrooms: 4

    Bathrooms : 3

    Sleeping: 11

    Minimum night: 7

    Rent now

  21. Siesta Key Townhouse

  22. Siesta Key Townhouse

    Not only does this townhouse have a private pool, but it is also less than a five minute walk to Siesta Key Beach and Siesta Key Village. Beach towels and chairs are provided. Between the garages and the driveway there is parking for up to four cars. Take the tip-only shuttle service around the key. Discounts on bike rentals, kayaks, paddleboards, and boat tours are also offered.

    Bedrooms: 4

    Bathrooms : 2.5

    Sleeping: 12

    Minimum night: Varied

    Rent now

  23. House With Private Pool

  24. House With Private Pool

    Located in a quiet neighborhood just away from the village and the beach, this Siesta Key vacation rental sits on the corner of two canals. It offers direct access to the gulf, which is nice because it comes with a tandem kayak for guest use. Watch the boats come in and out of the pool and keep an eye out for ospreys and great white egrets that roam the property’s lush landscape. Walk down the street to see the sun set over the gulf, then head to a restaurant for dinner.

    Bedrooms: 4

    Bathrooms : 4

    Sleeping: 8

    Minimum night: 7

    Rent now

  25. House On Canal With Pool

  26. House On Canal With Pool

    Steps from Siesta Key Beach, this four-bedroom vacation home sits on historic Cape Leyte Drive. Watch the sun go down from the pool and hot tub. For those traveling with small children, this rental provides a crib, stroller, toys, books, board games, toddler bike with training wheels, and helmets. There is also a beach cart, fishing rods and a bicycle trailer.

    Bedrooms: 4

    Bathrooms : 3.5

    Sleeping: 8

    Minimum night: Varied

    Rent now

  27. Canal House With Pool

  28. Canal House With Pool

    Located on the beautiful network of canals, this Siesta Key vacation rental is perfect for those planning to bring or rent a boat, as you can pull it right up to the house. This five bedroom home also has a heated swimming pool. Siesta Village and the beach are within walking distance, but if you prefer to drive to the beach, the host has a parking space on the beach for guests. Two tenants share the property and parking but do not have access to the yard, pool, house or canal.

    Bedrooms: 5

    Bathrooms : 5

    Sleeping: ten

    Minimum night: 7

    Rent now

  29. Siesta Key Village Home With Pool

  30. Siesta Key Village Home With Pool

    We saved the best for last! This seven-bedroom vacation rental will set you back a pretty penny, but you can share it with up to 17 other people. Offer Over 3,000 square feet of outdoor space, this vacation home features a heated pool with a waterslide and beach entrance, sun shelf, and hot tub. Gulf views can be seen from multiple levels, including the rooftop deck. There is even an elevator!

    Located in the heart of Siesta Key Village, this home is just a few houses from the beach. Beach towels and beach chairs are included, as is parking for up to four cars. Everything – including the beach, restaurants and shops – is just a one minute walk from this great location. It can even accept pets for an additional fee.

    Bedrooms: 7

    Bathrooms : 7.5

    Sleeping: 18

    Minimum night: Varied

    Rent now

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