The 10 best holiday homes in Siesta Key, USA | Booking.com
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Holiday Homes in Siesta Key

Find the holiday homes that appeal to you the most

Holiday Homes for every style

Find the right holiday home for you in Siesta Key

The best holiday homes in Siesta Key

Check out our pick of great holiday homes in Siesta Key

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Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes 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.

  • Situated in Sarasota, 1.4 km from Siesta Key Beach and 16 km from John And Mable Ringling Museum Of Art, Siesta Key Paradise, Vacation Pool Home, Near Beach, Restaurants and More offers air...

  • 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.

Great access to the city centre. Check these holiday homes in Siesta Key and nearby

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

  • 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.

  • 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.

  • Located in Siesta Key, 2.2 km from Siesta Key Beach and 16 km from The John And Mable Ringling Museum Of Art, New Listing! Spacious, 100 percent Private, near the Siesta Key Beach and Village!

  • Crescent Royale 515, a property with massage services, is located in Siesta Key, 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art, as well as 20...

  • Crescent Royale 105, a property with massage services, is set in Siesta Key, 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art, as well as 20 km...

  • Crescent Royale 509, a property with massage services, is located in Siesta Key, 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art, as well as 20...

  • Crescent Royale 415, a property with massage services, is located in Siesta Key, 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art, as well as 20...

Save money on holiday homes in Siesta Key and nearby – budget options available

  • Tiny House Siesta

    Sarasota
    Budget options available
    Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 634 reviews

    Tiny House Siesta offers self-catering tiny houses in Sarasota, Florida. Features include a kitchenette, TV, and free WiFi. Siesta Key is less than 1 km away and Siesta Key Beach is 1.6 km away.

    From US$167.24 per night
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Set 21 km from John And Mable Ringling Museum Of Art, Cute 3/2 Siesta home steps from Siesta waters offers accommodation with free WiFi and free private parking.

    From US$357.81 per night

  • Crescent Royale 407

    Siesta Key
    Budget options available

    Situated in Siesta Key, 300 metres from Siesta Key Beach and 18 km from John And Mable Ringling Museum Of Art, Crescent Royale 407 offers massage services and air conditioning.

  • Crescent Royale 409

    Siesta Key
    Budget options available

    Crescent Royale 409, a property with massage services, is situated in Siesta Key, 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art, as well as 20...

  • Crescent Royale 511

    Siesta Key
    Budget options available

    Crescent Royale 511, a property with massage services, is located in Siesta Key, 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art, as well as 20...

  • Crescent Royale 201

    Siesta Key
    Budget options available

    Crescent Royale 201, a property with massage services, is located in Siesta Key, 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art, as well as 20...

  • Crescent Royale 501

    Siesta Key
    Budget options available

    Crescent Royale 501, a property with massage services, is located in Siesta Key, 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art, as well as 20...

  • Crescent Royale 203

    Siesta Key
    Budget options available

    Located 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art and 20 km from Sarasota International Convention Center, Crescent Royale 203 features...

FAQ about holiday homes in Siesta Key

Holiday homes that guests love in Siesta Key

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  • Siesta Key Bay View Beach Access

    Holiday Home in Siesta Key
    Scored out of 10, guest rating 7.9
    Good - What previous guests thought, 65 reviews
    The house is in a beautiful, peaceful and tranquil setting. A fresh, clean scent was very noticeable upon opening the door on arrival. The house was very clean. Pool off slider of master bedroom was perfect for swimming later in the day when it was too hot to be at the beach. Great water pressure in master shower. Great location for taking the trolley to Siesta Key Village for dinner.
    Guest review by
    Lynn
    Family with young children

  • Sea Foam - 173

    Holiday Home in Siesta Key
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 3 reviews
    The location was perfect! The unit was very clean and the kitchen was stocked with everything we needed. Very good communication leading up to our stay.
    Guest review by
    Michelle
    Solo traveller

  • Bayside Escape - 1345

    Holiday Home in Siesta Key
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 4 reviews
    Spacious waterfront property within walking distance of the beach. Felt miles away from the traffic and crowds. So many extras from cupcakes upon arrival, to all the things needed for a day at the beach. Modern, updated and very clean. Will recommend and return!!
    Guest review by
    Jennifer
    Solo traveller

  • Siesta Heron Suites & Villas

    Holiday Home in Siesta Key
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 205 reviews
    Very clean.. close to the main beaches and it is comfortable...
    Guest review by
    José Roberto
    Family with young children