The 10 best holiday rentals in Siesta Key, USA | Booking.com
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Holiday Rentals in Siesta Key

Find the holiday rentals that appeal to you the most

The best holiday rentals in Siesta Key

Check out our pick of great holiday rentals in Siesta Key

Most booked holiday rentals in Siesta Key and surroundings in the past month

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Enjoy breakfast in Siesta Key and nearby

  • Featuring air-conditioned accommodation with a private pool, The Sun Dial - 827 is located in Siesta Key. This property offers access to a balcony, free private parking and free WiFi.

  • Boasting air-conditioned accommodation with a private pool, Sand Dollar Cottage - 910 is set in Siesta Key. This property offers access to a balcony, free private parking and free WiFi.

  • Set in Sarasota, within 600 metres of Siesta Key Beach and 17 km of The John And Mable Ringling Museum Of Art, Oasis on Siesta Key offers accommodation with free WiFi, air conditioning, water sports...

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

    Featuring air-conditioned accommodation with a private pool, Villa Champagne - 5322 is located in Siesta Key. This property offers access to a balcony, free private parking and free WiFi.

  • Located in Siesta Key, Beach Palm Villa - 5533 provides accommodation with private pool, free WiFi and free private parking for guests who drive.

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

    Set in Siesta Key, La Contento Casa - 5560 offers accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Isla Amor - 86

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

    Boasting air-conditioned accommodation with a private pool, Isla Amor - 86 is situated in Siesta Key. This property offers access to a balcony, free private parking and free WiFi.

  • Featuring air-conditioned accommodation with a private pool, Siesta Key Beach - Cape Aqua 5545 is located in Siesta Key.

Highly rated holiday 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 529 metres from Siesta Beach, Tropical Breeze Resort features two heated on-site pools and a spa. Guests will be 15 km from Mote Marine Laboratory and Aquarium.

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

    Featuring air-conditioned accommodation with a private pool, garden view and a balcony, Sarasota Updated pool home, Near Siesta Key is located in Sarasota.

    From US$708.98 per night
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 53 reviews

    Located in Sarasota, Florinda 3bdr/2bth 2car garage with New Pool provides accommodation with private pool, free WiFi and free private parking for guests who drive.

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

    3 miles to Siesta Key #1 Beach in America is located in Sarasota, 11 km from Marina Jack Restaurant And Marina, 12 km from Sarasota County Visitor Information Center And History Museum, and 15 km from...

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

    Featuring air-conditioned accommodation with a patio, Close to beaches with hot tub and large garden is located in Sarasota.

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

    4 miles to Siesta Key Beach #1 in America is set in Sarasota, 12 km from Sarasota Opera, 12 km from Marina Jack Restaurant And Marina, as well as 13 km from Sarasota County Visitor Information Center...

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

    House by Siesta Key, a property with a garden, is set in Sarasota, 11 km from Marina Jack Restaurant And Marina, 13 km from Sarasota County Visitor Information Center And History Museum, as well as 15...

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

    Situated in Sarasota, Shiny oasis with lake view features accommodation with a heated pool and garden views.

    From US$329.87 per night

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

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

    Boasting air-conditioned accommodation with a private pool, MERMAID HOUSE WITH POOL JACUZZI STEPS to SIESTA KEY BEACH is set in Sarasota.

    From US$785.07 per night
  • 2BR / 2BA Apartment Sienna Park.

    Sarasota
    Free cancellation options available

    Situated in Sarasota, 2BR / 2BA Apartment Sienna Park. Offers accommodation with a heated pool.

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

    Set in Sarasota, Bernice 3bd2bth With Heated Pool Near Siesta Key! offers accommodation with private pool, free WiFi and free private parking for guests who drive.

    From US$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

    Situated in Vamo, LUX VILLAs on beautiful Palmer Ranch offers a balcony with lake and pool views, as well as a year-round outdoor pool, hot tub and fitness centre.

    From US$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

    The Julia Place Carriage House features accommodation located less than 1 km from the centre of Sarasota and offers a garden and a terrace.

    From US$261.98 per night
  • Gulf Birdie - 5551

    Siesta Key
    Free cancellation options available

    Featuring air-conditioned accommodation with a private pool, Gulf Birdie - 5551 is located in Siesta Key. This property offers access to a balcony, free private parking and free WiFi.

  • Central - Edgemere 738

    Siesta Key
    Free cancellation options available

    Featuring air-conditioned accommodation with a private pool, Central - Edgemere 738 is set in Siesta Key. The 4-star holiday home is 10 km from Sarasota Opera.

  • 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

    Set in Siesta Key and only 200 metres from Siesta Key Beach, Beach Way Getaway offers accommodation with sea views, free WiFi and free private parking.

FAQ about holiday rentals in Siesta Key

Holiday 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
    Fabulous - 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
    Superb - What previous guests thought, 210 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
    People 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