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

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Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Key

Siesta Cooler: Only Minutes Walk to Siesta Beach! is situated in Siesta Key, 16 km from The John And Mable Ringling Museum Of Art, 18 km from Sarasota International Convention Center, as well as 10 km...

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 16 reviews
Location 9.4
Price from
US$157.64
1 night, 2 adults

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 8.4
Very good - What previous guests thought, 210 reviews
Location 8.6
Price from
US$119.57
1 night, 2 adults

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
Location 8.3
Price from
US$105.80
1 night, 2 adults

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, 55 reviews
Location 9.1
Price from
US$133.14
1 night, 2 adults

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 8.9
Fabulous - What previous guests thought, 19 reviews
Location 9.2
Price from
US$178.16
1 night, 2 adults

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, 22 reviews
Location 10.0
Price from
US$107.87
1 night, 2 adults

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, 41 reviews
Location 9.2
Price from
US$202.40
1 night, 2 adults

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 9.8
Exceptional - What previous guests thought, 8 reviews
Location 10.0
Price from
US$36.80
1 night, 2 adults

* NEW * Serene Retreat / Private Patio & Pool *

Sarasota (Near Siesta Key)

Set in Sarasota, * NEW * Serene Retreat / Private Patio & Pool * offers 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, 5 reviews
Location 9.0
Price from
US$183.33
1 night, 2 adults

House by Siesta Key

Sarasota (Near Siesta Key)

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...

R
Rebecca
From
United States
Liked that it was clean. The host was super!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 8 reviews
Location 9.0
Price from
US$97.25
1 night, 2 adults
All 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.

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.

  • Tropical Breeze Resort

    Sarasota
    Free cancellation options available
    Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 283 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$356.92 per night
  • Florinda 3bdr/2bth 2car garage with New Pool

    Sarasota
    Free cancellation options available
    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.

  • 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 8.5
    Very good - What previous guests thought, 41 reviews

    Offering a garden and garden view, Entire Guesthouse 5 mins to Siesta Key & downtown is situated in Sarasota, 5.4 km from Marina Jack Restaurant And Marina and 6.9 km from Sarasota County Visitor...

    From US$196.94 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$376.88 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

Highly rated holiday rentals in Siesta Key and nearby

  • 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, 69 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 9.4
    Superb - What previous guests thought, 6 reviews

    Featuring air-conditioned accommodation with a private pool, pool view and a patio, Pool Home on Gulf Gate 5min away from Siesta Key is located in Sarasota.

    From US$3,640 per night
  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 20 reviews

    Located in Sarasota, 17 km from The John And Mable Ringling Museum Of Art and 12 km from Sarasota Opera, 2BR/1BA Sienna Park Apartment provides air-conditioned accommodation with a balcony and free...

    From US$386.40 per night
  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 21 reviews

    Located in Sarasota, 17 km from John And Mable Ringling Museum Of Art and 18 km from The John And Mable Ringling Museum Of Art, 1+1 Large condo Sarasota offers an outdoor swimming pool and air...

    From US$358.40 per night

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, 22 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, 209 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
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