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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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Popular with guests booking holiday rentals in Siesta Key

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 109 reviews

Popular with guests booking holiday rentals in Siesta Key

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 17 reviews

Popular with guests booking holiday rentals in Siesta Key

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 13 reviews

Popular with guests booking holiday rentals in Siesta Key

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 9 reviews

Popular with guests booking holiday rentals in Siesta Key

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 57 reviews

Popular with guests booking holiday rentals in Siesta Key

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 26 reviews

Popular with guests booking holiday rentals in Siesta Key

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 66 reviews

Popular with guests booking holiday rentals in Siesta Key

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 188 reviews

Popular with guests booking holiday rentals in Siesta Key

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 54 reviews

Popular with guests booking holiday rentals in Siesta Key

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 206 reviews

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.

Oasis on Siesta Key is a beachfront property set in Sarasota, 600 metres from Siesta Key Beach and 17 km from The John And Mable Ringling Museum Of Art.

Scored out of 10, guest rating 10
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.

Featuring air-conditioned accommodation with a private pool, Beach Palm Villa - 5533 is located in Siesta Key. This property offers access to a balcony, free private parking and free WiFi.

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

Boasting air-conditioned accommodation with a private pool, La Contento Casa - 5560 is set in Siesta Key. This property offers access to a balcony, free private parking and free WiFi.

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

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

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.

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

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 4 reviews

Boasting a year-round outdoor pool and a hot tub, Pink Flamingo Unit, Steps to Beach, Siesta Key Village & Pet-Friendly is located in Siesta Key, 1.3 km from Crescent Beach and 17 km from John And...

From US$621.38 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 1 review

Featuring air-conditioned accommodation with a private pool, Jellyfish-Flamingo House, Amazing Location On Beach & Walk To Village is located in Siesta Key.

From US$1,220.88 per night
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.

Siesta Key Beach Resort and Suites

Sarasota
Free cancellation options available
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 671 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, 395 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$292.03 per night

Tropical Breeze Resort

Sarasota
Free cancellation options available
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 281 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$371.86 per night
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 31 reviews

Boasting air-conditioned accommodation with a pool with a view, Luxury Zen Den with heated pool just off Siesta Key is set in Sarasota.

From US$281.37 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, 58 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.

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$657.34 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 21 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$357.38 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 64 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 9.1
Superb - What previous guests thought, 15 reviews

Located in Sarasota, 200 metres from Crescent Beach and 18 km from John And Mable Ringling Museum Of Art, One Ocean - A 1101 offers air conditioning.

From US$425.23 per night
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 42 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$238.16 per night
Scored out of 10, guest rating 9.3
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.

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 9.2
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$326.33 per night

Holiday Rentals with swimming pools in Siesta Key and nearby

Scored out of 10, guest rating 5.0
Passable - What previous guests thought, 1 review

Featuring a garden, private pool and garden views, #1US Siesta Key Beach Pool House is located in Siesta Key.

From US$565 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Set in Sarasota, Siesta Key Waterfront Estate W Pool Privacy! offers accommodation with private pool, free WiFi and free private parking for guests who drive.

From US$1,225.93 per night

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

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 49 reviews

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

From US$329.87 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$375.20 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 13 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$369.60 per night
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 8 reviews

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.

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 8.7
Fabulous - 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, 57 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, 206 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 7.2
Good - What previous guests thought, 27 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