The 10 best vacation rentals in Siesta Key, US | Booking.com
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Vacation Rentals in Siesta Key

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The best vacation rentals in Siesta Key

Check out our selection of great vacation rentals in Siesta Key

Most booked vacation rentals in Siesta Key and surrounding area in the past month

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Enjoy breakfast in Siesta Key and nearby

  • The Sun Dial - 827 offers accommodations in Siesta Key, 1.1 miles from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

  • Sand Dollar Cottage - 910 offers accommodations in Siesta Key, a 15-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

  • A 6-minute walk from Siesta Key Beach in Sarasota, Oasis on Siesta Key features accommodations with access to a fitness room.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Villa Champagne - 5322 is located in Siesta Key, just a 9-minute walk from Siesta Key Beach and 11 miles from The John and Mable Ringling Museum of Art.

  • Beach Palm Villa - 5533 is located in Siesta Key, just a 11-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

  • Scored out of 10, guest rating 8.0
    Very Good - What previous guests thought, 1 review

    La Contento Casa - 5560 is located in Siesta Key, just a 15-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

  • Isla Amor - 86

    Siesta Key
    Breakfast options
    Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 1 review

    Isla Amor - 86 is located in Siesta Key, just a 7-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

  • Siesta Key Beach - Cape Aqua 5545 is located in Siesta Key, just a 10-minute walk from Siesta Key Beach and 11 miles from The John and Mable Ringling Museum of Art.

Highly rated vacation rentals in Siesta Key and nearby

  • Scored out of 10, guest rating 8.2
    Very Good - What previous guests thought, 282 reviews

    Spanning 2 city blocks and located just 1736 feet from Siesta Beach, Tropical Breeze Resort features two heated on-site pools and a spa. Guests will be 9.3 mi from Mote Marine Laboratory and Aquarium.

    From $327.06 per night
  • Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 10 reviews

    Sarasota Updated pool home, Near Siesta Key is located in Sarasota, just 10 miles from John and Mable Ringling Museum of Art and 10 miles from The John and Mable Ringling Museum of Art.

    From $657.34 per night
  • Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 53 reviews

    Florinda 3bdr/2bth 2car garage with New Pool is located in Sarasota, just 7.8 miles from The John and Mable Ringling Museum of Art and 4.2 miles from Sarasota Opera.

  • Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 68 reviews

    3 miles to Siesta Key #1 Beach in America offers accommodations in Sarasota, 6.7 miles from Sarasota Opera and 6.8 miles from Marina Jack Restaurant And Marina.

    From $277.72 per night
  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 41 reviews

    10 miles from The John and Mable Ringling Museum of Art in Sarasota, Close to beaches with hot tub and large garden provides accommodations with access to a hot tub.

    From $245.05 per night
  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 50 reviews

    4 miles to Siesta Key Beach #1 in America is located in Sarasota, just 11 miles from The John and Mable Ringling Museum of Art and 7.1 miles from Sarasota Opera.

    From $250.76 per night
  • Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 8 reviews

    House by Siesta Key offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.1 miles from Sarasota Opera.

    From $321.17 per night
  • Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 51 reviews

    Providing an outdoor swimming pool, Shiny oasis with lake view features accommodations in Sarasota.

    From $329.87 per night

These vacation rentals in Siesta Key and nearby have options with free cancellation

  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 4 reviews

    Offering a bar, MERMAID HOUSE WITH POOL JACUZZI STEPS to SIESTA KEY BEACH offers accommodations in Sarasota. This beachfront property offers access to a terrace, free private parking, and free Wifi.

    From $752.62 per night
  • 2BR / 2BA Apartment Sienna Park.

    Sarasota
    Free cancellation options available

    2BR / 2BA Apartment Sienna Park. Is located in Sarasota, just 1.8 miles from Crescent Beach and 10 miles from John and Mable Ringling Museum of Art.

    From $385.16 per night
  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 29 reviews

    Bernice 3bd2bth With Heated Pool Near Siesta Key! offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.7 miles from Sarasota Opera.

    From $487.24 per night
  • LUX VILLAs on beautiful Palmer Ranch

    Vamo
    Free cancellation options available
    Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 45 reviews

    13 miles from The John and Mable Ringling Museum of Art in Vamo, LUX VILLAs on beautiful Palmer Ranch features accommodations with access to a hot tub, fitness center, and open-air bath.

    From $427.84 per night
  • The Julia Place Carriage House

    Sarasota
    Free cancellation options available
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 23 reviews

    Providing a garden, The Julia Place Carriage House features accommodations in Sarasota.

    From $261.98 per night
  • Gulf Birdie - 5551

    Siesta Key
    Free cancellation options available

    Gulf Birdie - 5551 is located in Siesta Key, just a 15-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

  • Central - Edgemere 738

    Siesta Key
    Free cancellation options available

    Central - Edgemere 738 is located in Siesta Key, just 10 miles from The John and Mable Ringling Museum of Art and 6 miles from Sarasota Opera. Guests may go for a swim in the private pool.

  • Beach Way Getaway

    Siesta Key
    Free cancellation options available
    Scored out of 10, guest rating 8.0
    Very Good - What previous guests thought, 1 review

    Beach Way Getaway is located in Siesta Key, just 11 miles from John and Mable Ringling Museum of Art and 11 miles from The John and Mable Ringling Museum of Art.

FAQ about vacation rentals in Siesta Key

Vacation Rentals That Guests Love in Siesta Key

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  • Scored out of 10, guest rating 8.4
    Very Good - What previous guests thought, 21 reviews
    Great location. Very close to trolley stops, within walking distance of the village and very easy access to beach.
    Guest review by
    Amanda
    Young couple
  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 55 reviews
    Property was in the perfect location! Close walk to the beach and the village! Perfect little beach house with an adorable pool!
    Guest review by
    Kristin
    Family with young children
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 211 reviews
    The place was perfect!!! Nice and clean. Close to Siesta Key Village and next to the beach. We stayed in cottage 1, and the outside shower was amazing. Have private sitting area and fish pond is right outside out front door. Definitely will be staying again.
    Guest review by
    Sandy
    Travelers with friends
  • Scored out of 10, guest rating 8.3
    Very Good - What previous guests thought, 20 reviews
    My husband and I stayed here last November so knew what to expect. The beach wagon comes in so handy when walking to the village for groceries. Both times staying here the place was so clean!
    Guest review by
    Tisha
    Family with young children
  • Scored out of 10, guest rating 7.3
    Good - What previous guests thought, 28 reviews
    Easy access to private beach, close to everything (in between siesta key village and downtown), easy to access, clean, more than adequate for vacation home, pools were never overcrowded and there were two.
    Guest review by
    Olivia
    Family with young children