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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

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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Popular with guests booking holiday homes in Siesta Key

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 1 review

Popular with guests booking holiday homes in Siesta Key

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 12 reviews

Popular with guests booking holiday homes in Siesta Key

Popular with guests booking holiday homes in Siesta Key

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 58 reviews

Popular with guests booking holiday homes in Siesta Key

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

Popular with guests booking holiday homes in Siesta Key

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

Popular with guests booking holiday homes in Siesta Key

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

Popular with guests booking holiday homes in Siesta Key

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

Popular with guests booking holiday homes in Siesta Key

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 55 reviews

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

Featuring air-conditioned accommodation with a private pool, Jellyfish Unit, Walk to Beach & Siesta Key Village, Pet-Friendly is set in Siesta Key.

From US$579.54 per night
Scored out of 10, guest rating 8.7
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$623.80 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$1,224.51 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Boasting air-conditioned accommodation with a private pool, Mermaid-Shark 6BR House With Pool, Jacuzzi - Steps to Siesta Key Beach is set in Siesta Key.

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.

Featuring a private pool and sea views, Siesta Dreamin' is located in Siesta Key.

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.

Holiday Homes with swimming pools in Siesta Key and nearby

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.

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 670 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
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
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
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
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Boasting air-conditioned accommodation with a private pool, Enchanted & peaceful Oasis 10 min away from one of the most beautiful beaches in the World Siesta key is situated in Sarasota.

From US$412.20 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 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

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

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 3 reviews

Set in Sarasota, 2.5 km from Crescent Beach and 16 km from John And Mable Ringling Museum Of Art, Eco Private Suite Rm w Bath Golf Nearby J2A shared home offers air-conditioned accommodation with a...

From US$116.03 per night
Scored out of 10, guest rating 5.0
Passable - What previous guests thought, 3 reviews

Situated in Sarasota, 2.5 km from Crescent Beach and 16 km from John And Mable Ringling Museum Of Art, Cozy Private Rm Near Beach Travelers Welcome J1A shared home features air-conditioned...

From US$117.92 per night
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 4 reviews

Located in Sarasota, 16 km from John And Mable Ringling Museum Of Art and 16 km from The John And Mable Ringling Museum Of Art, Cozy Retreat pvt rm Close To Siesta Keys J3A shared home offers a garden...

Tiny House Siesta

Sarasota
Budget options available
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 633 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$186.47 per night

Set in Siesta Key, 2 km from Crescent Beach and 16 km from John And Mable Ringling Museum Of Art, Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach offers air conditioning.

From US$182.84 per night

Situated in Sarasota, 7.4 km from The John And Mable Ringling Museum Of Art and 8.6 km from Sarasota International Convention Center, Comfortable Stay Near Golf Attractions Rm3 shared home offers a...

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

Located in Sarasota, 7.4 km from The John And Mable Ringling Museum Of Art and 8.6 km from Sarasota International Convention Center, Private Stay Near Ed Smith Stadium-Great Location Rm4 Shared home...

From US$117.92 per night

Situated in Sarasota, 7.4 km from The John And Mable Ringling Museum Of Art and 8.6 km from Sarasota International Convention Center, Bright Private Room Ideal for Long or Short Stay Rm1 Shared home...

Enjoy breakfast in Siesta Key and nearby

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.

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.

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...

Located in Siesta Key, Bikini Tini Time provides 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.

Boasting air-conditioned accommodation with a private pool, Poseidons Palace is situated in Siesta Key.

FAQ about holiday homes in Siesta Key

Holiday homes that guests love in Siesta Key

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Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 66 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
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
Avg. price/night: US$405.34
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 188 reviews
Very clean.. close to the main beaches and it is comfortable...
Guest review by
José Roberto
Family with young children