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 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, 56 reviews
Price from
US$346.38
1 night, 2 adults

Beautiful property on Siesta Key

Siesta Key

Featuring air-conditioned accommodation with a private pool, garden view and a patio, Beautiful property on Siesta Key is located in Siesta Key.

P
Pauline
From
United Kingdom
I spent a month in this fabulous property. It was so comfortable it felt like I had lived there forever. Kitchen had everything I needed. Pool was great but it was just minutes from the beach and dock. Do yourselves a favour and book this property you will not be disappointed
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 53 reviews
Price from
US$200
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, 6 reviews
Price from
US$183.33
1 night, 2 adults

Shiny oasis with lake view

Sarasota (Near Siesta Key)

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

J
JennieYY
From
Switzerland
The location is great! Bed is comfortable and easy check in and check out. We enjoy the view from the balcony and we can see rabbits outside. Anita is very responsive.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 51 reviews
Price from
US$170.15
1 night, 2 adults

Close to beaches with hot tub and large garden

Sarasota (Near Siesta Key)

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

J
Joanna
From
Ireland
Nice holiday house. 10 minutes drive to Siesta Key beach.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 41 reviews
Price from
US$185.25
1 night, 2 adults

Pool Home on Gulf Gate 5min away from Siesta Key

Sarasota (Near Siesta Key)

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.

H
Helen
From
United Kingdom
We all thoroughly enjoyed our stay here. I have been many times to Sarasota and this was the best house that we have stayed in. It is close to the beach and all the shops.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 6 reviews
Price from
US$3,000
1 night, 2 adults

2BR/1BA Sienna Park Apartment

Sarasota (Near Siesta Key)

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...

D
Dalia
From
Canada
Everything was great! Everything we needed for our stay. Very comfortable beds, quiet area, washer/dryer, excellent internet, pool. Eva and her husband were very attentive Very pleased. We will be back.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 20 reviews
Price from
US$130
1 night, 2 adults

2BR/1BA Vacation Rental - Sienna Park

Sarasota (Near Siesta Key)

Set in Sarasota, 2BR/1BA Vacation Rental - Sienna Park features a pool with a view.

P
Peter
From
Hungary
Score: 10 points. What else? Everything was perfect. And this app gives much more than others. Thank you!
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 25 reviews
Price from
US$120
1 night, 2 adults

2BR/2BA condo Sienna Park

Sarasota (Near Siesta Key)

Located in Sarasota, the recently renovated 2BR/2BA condo Sienna Park provides accommodation 18 km from John And Mable Ringling Museum Of Art and 18 km from The John And Mable Ringling Museum Of Art.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 8 reviews
Price from
US$100
1 night, 2 adults

Siesta Key Beachside Villas

Sarasota (Near Siesta Key)

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.

S
Sybil
From
United States
Loved the room. So pretty and updated. Beautiful shower. Location was perfect. Very short stroll to beach. And steps away from all the good restaurants.
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 394 reviews
Price from
US$228.33
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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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$668.57 per night
  • Siesta Key Beach Resort and Suites

    Sarasota
    Free cancellation options available
    Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 687 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.

    From US$308.21 per night
  • Siesta Key Beachside Villas

    Sarasota
    Free cancellation options available
    Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 394 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.

    From US$313.97 per night
  • 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$341.99 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, 55 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.

  • Crescent Beach 1011 #1

    Sarasota
    Free cancellation options available
    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...

    From US$373.05 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...

  • 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

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$618.30 per night
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 67 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, 19 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

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.

FAQ about holiday rentals in Siesta Key

Holiday rentals that guests love in Siesta Key

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  • Avg. price/night: US$364.42
    Scored out of 10, guest rating 8.5
    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, 56 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, 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
  • 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