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

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The best holiday rentals in Siesta Key

Check out our pick of great holiday rentals in Siesta Key

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Siesta Heron Suites & Villas

Siesta Key

Offering an outdoor swimming pool and pool view, Siesta Heron Suites & Villas is situated in Siesta Key, 20 km from The John And Mable Ringling Museum Of Art and 14 km from Sarasota Opera.

J
José Roberto
From
Brazil
Very clean.. close to the main beaches and it is comfortable...
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 213 reviews
Price from
US$320.03
1 night, 2 adults
Check availability

Heat of Siesta Village Walk to Beach w heated Pool

Siesta Key

Featuring air-conditioned accommodation with a patio, Heat of Siesta Village Walk to Beach w heated Pool is located in Siesta Key.

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 13 reviews
Price from
US$297.21
1 night, 2 adults
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Siesta Key Island Rentals

Siesta Key

Boasting pool views, Siesta Key Island Rentals provides accommodation with an outdoor swimming pool, an indoor pool and a garden, around 400 metres from Siesta Key Beach.

L
Luisa
From
United Arab Emirates
The cottage had really everything you need for a vacation by the beach.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 53 reviews
Price from
US$338.91
1 night, 2 adults
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Siesta Key Beach 665 #1

Siesta Key

Siesta Key Beach 665 #1 is located in Siesta Key, 11 km from Sarasota Opera, 11 km from Marina Jack Restaurant And Marina, as well as 13 km from Sarasota County Visitor Information Center And History...

A
Anna Nilsson
From
Sweden
We did our own breakfast in the kitchen. Next to the beach and close to supermarket and entertainment.
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 18 reviews
Price from
US$474.55
1 night, 2 adults
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Siesta Key Beach - Capri 665 #4

Siesta Key

Siesta Key Beach - Capri 665 #4 is located in Siesta Key, 18 km from The John And Mable Ringling Museum Of Art, 20 km from Sarasota International Convention Center, and 12 km from Marina Jack...

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 21 reviews
Price from
US$324.93
1 night, 2 adults
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Siesta Key Beach - Bari 665 #2

Siesta Key

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, Siesta Key Beach - Bari 665 #2...

I
Ilyas
From
Germany
Location is perfect, has what it needs, nice shower, plenty of towels, easy check in and out
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 23 reviews
Price from
US$310.83
1 night, 2 adults
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Siesta Key Condo - on the water !

Siesta Key

Featuring air-conditioned accommodation with a pool with a view, Siesta Key Condo - on the water! is situated in Siesta Key.

K
Kristina
From
Lithuania
Although we didn’t meet the hosts in person, from our communication we can say they are wonderful, kind, and genuinely friendly people. Their condo is cozy and full of old Florida charm, with everything you could possibly need for your vacation stay. And I’m not just talking about the kitchen with not one but two coffee makers – they also provide all the beach gear you might need: a cart, beach towels, beach chairs, two umbrellas, and even simple toys for your kids. You really don’t have to worry about bringing anything! It’s about a 10-minute leisurely walk to the beach, which has a private entrance, so it’s never overcrowded and there’s plenty of space if you want more privacy. The sand is white, there was no red tide during our stay, and we had an amazing time. On top of that, the complex has a great pool, which is regularly cleaned by a friendly lady, and the water is pleasantly warm. There are loungers by the pool and on the grassy area by the water, where you can sunbathe, read, or simply watch pelicans flying overhead. You can even bring pizza and enjoy it with a view of the water. If you’d like to visit Siesta Key’s main beach but don’t want to deal with parking, there’s a nearby trolley stop that offers free rides around the island. Just download the app to see the exact schedule. All in all, we were truly impressed by the comfort, coziness, and great value for the price. We can wholeheartedly recommend this place.
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 43 reviews
Price from
US$330
1 night, 2 adults
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Location Siesta 1 mile away Home with HOT SPA

Sarasota (Near Siesta Key)

Boasting a garden, private pool and pool views, Location Siesta 1 mile away Home with HOT SPA is situated in Sarasota.

J
Jennifer
From
United States
It is a beautiful property in a great location, everything is close by. The owner has made it a pleasure to visit, comfortable clean and has a real homely feel. The unit has everything you could think of and need. You only need to turn up with your clothes and toothbrush and cater for yourself. We were very sad to have to go home. We would highly recommend this place and will be definitely returning.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 11 reviews
Price from
US$559.68
1 night, 2 adults
Check availability

Vintage Vibes - Grill, Chill & Beach Thrills

Sarasota (Near Siesta Key)

Situated in Sarasota in the Florida region, Vintage Vibes - Grill, Chill & Beach Thrills features a patio. This property offers access to a terrace, free private parking and free WiFi.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 7 reviews
Price from
US$234.84
1 night, 2 adults
Check availability

Florinda 3bdr/2bth 2car garage with New Pool

Sarasota (Near Siesta Key)

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.

I
Ian
From
United Kingdom
Location to key beaches and downtown Sarasota was excellent. Clean and very comfortable with everything you would need.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 50 reviews
Price from
US$536.39
1 night, 2 adults
Check availability
All holiday rentals in Siesta Key

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

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Highly rated holiday rentals in Siesta Key and nearby

  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 720 reviews

    Located just 1 minutes’ walk from the beach, this Siesta Key resort features a swimming pool. Guests can also enjoy access to free WiFi in common areas.

  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 407 reviews

    Siesta Key Beachside Villas is located in the heart of Siesta Key. It features an outdoor pool and free WiFi. Beach access is a 2 minutes' walk from the property.

  • Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 291 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.

  • Scored out of 10, guest rating 8.8
    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.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 50 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 9.6
    Exceptional - What previous guests thought, 11 reviews

    Boasting a garden, private pool and pool views, Location Siesta 1 mile away Home with HOT SPA is situated in Sarasota.

  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 24 reviews

    Crescent Beach 1011 #1, a property with an outdoor swimming pool, is located in Sarasota, 18 km from The John And Mable Ringling Museum Of Art, 20 km from Sarasota International Convention Center, as...

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 39 reviews

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

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...

  • Featuring air-conditioned accommodation with a balcony, Serene Siesta Key is located in Siesta Key. Guests can benefit from a patio and an outdoor pool.

  • 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.

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

    Featuring air-conditioned accommodation with a private pool, Avenida Sanctuary is located in Siesta Key.

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

  • Shiny oasis with lake view

    Sarasota
    Free cancellation options available
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 51 reviews

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

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 28 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.

  • LUX VILLAs on beautiful Palmer Ranch

    Vamo
    Free cancellation options available
    Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 46 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.

  • Canopy Cottage on Siesta Key

    Siesta Key
    Free cancellation options available

    Set in Siesta Key, Canopy Cottage on Siesta Key offers accommodation with a private pool.

  • Isla Amor - 86

    Siesta Key
    Free cancellation options available
    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.

  • Siesta Key Beach - Cape Aqua 5545

    Siesta Key
    Free cancellation options available

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

  • 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.

FAQ about holiday rentals in Siesta Key

Holiday rentals that guests love in Siesta Key

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  • Siesta Key Beach - Capri 665 #4

    Holiday Rental in Siesta Key
    Avg. price/night: US$394.04
    Scored out of 10, guest rating 8.0
    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

  • Siesta Key Island Rentals

    Holiday Rental in Siesta Key
    Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 53 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

  • BeachPoint Cottages

    Holiday Rental in Siesta Key
    Scored out of 10, guest rating 9.0
    Superb - 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
    People with friends

  • Walk to the beach - Island Villa

    Holiday Rental in Siesta Key
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 19 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

  • Palm Bay Club By Beachside Management

    Holiday Rental in Siesta Key
    Scored out of 10, guest rating 7.3
    Good - What previous guests thought, 30 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

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