Skip to main content

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

Filter by:

Review score

Siesta Key Island Rentals

Siesta Key

Situated within 400 metres of Siesta Key Beach and 16 km of The John And Mable Ringling Museum Of Art, Siesta Key Island Rentals provides rooms with air conditioning and a private bathroom in Siesta...

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$442.98
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 8.1
Very good - What previous guests thought, 53 reviews
Price from
US$200
1 night, 2 adults

Poolside Paradise Near Siesta Key Beach

Sarasota (Near Siesta Key)

Poolside Paradise Near Siesta Key Beach is located in Sarasota, 13 km from Marina Jack Restaurant And Marina, 13 km from Sarasota Opera, as well as 15 km from Sarasota County Visitor Information...

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 5 reviews
Price from
US$392.32
1 night, 2 adults

2bed/2bath Condo next to Siesta Key ~A Hidden Gem

Sarasota (Near Siesta Key)

Situated in Sarasota, 2bed/2bath Condo next to Siesta Key ~A Hidden Gem offers accommodation with a private pool. This property offers access to a balcony, free private parking and free WiFi.

C
Carrera
From
Netherlands
Beautiful villa! Great atmosphere, clean, great facilities and a great location
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 28 reviews
Price from
US$148.50
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

Tiny House Siesta

Sarasota (Near Siesta Key)

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.

R
REGINA
From
United States
I loved the location, the size of "The Starfish" was amazing! The house was very clean. Plenty of hot water :)
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 635 reviews
Price from
US$101
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, 397 reviews
Price from
US$228.33
1 night, 2 adults

Siesta Key Beach Resort and Suites

Sarasota (Near Siesta Key)

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.

M
MARY
From
United States
The location was amazing - across the street from the beach access and walking distance to the downtown shops and restaurants. The pool area was also wonderful!!
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 682 reviews
Price from
US$286.25
1 night, 2 adults

Sarasota Updated pool home, Near Siesta Key

Sarasota (Near Siesta Key)

Featuring air-conditioned accommodation with a private pool, garden view and a balcony, Sarasota Updated pool home, Near Siesta Key is located in Sarasota.

R
Rulo
From
United States
Location was good, home was nicely updated inside and overall comfortable.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 10 reviews
Price from
US$546.70
1 night, 2 adults

The Sapphire Suite

Sarasota (Near Siesta Key)

Situated in Sarasota, 600 metres from Indian Beach and 1.9 km from The John And Mable Ringling Museum Of Art, The Sapphire Suite offers a garden and air conditioning.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 12 reviews
Price from
US$93
1 night, 2 adults
All 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

See all

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 8.3
Very good - What previous guests thought, 24 reviews

Popular with guests booking holiday homes in Siesta Key

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

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 7.9
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, 197 reviews

Popular with guests booking holiday homes in Siesta Key

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 56 reviews

Popular with guests booking holiday homes in Siesta Key

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 23 reviews

Popular with guests booking holiday homes in Siesta Key

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

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, 681 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$336.46 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 397 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$352.96 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 22 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$394.98 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 9.0
Superb - What previous guests thought, 3 reviews

Located in Sarasota, Heated Pool Home - Close to Beaches, Restaurants & More! provides accommodation with private pool, free WiFi and free private parking for guests who drive.

From US$488.53 per night
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 44 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$356.50 per night

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

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

Tiny House Siesta

Sarasota
Budget options available
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 636 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$169.50 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...

From US$150.05 per night

The Sun Dial - 827

Siesta Key
Budget options available

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.

Sand Dollar Cottage - 910

Siesta Key
Budget options available

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

Sarasota
Budget options available

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...

Villa Champagne - 5322

Siesta Key
Budget options available
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.

Beach Palm Villa - 5533

Siesta Key
Budget options available

Located in Siesta Key, Beach Palm Villa - 5533 provides accommodation with private pool, free WiFi and free private parking for guests who drive.

La Contento Casa - 5560

Siesta Key
Budget options available
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.

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

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
Central location
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.

Cape Aqua

Siesta Key
Central location

Cape Aqua is set in Siesta Key, 17 km from John And Mable Ringling Museum Of Art, 17 km from The John And Mable Ringling Museum Of Art, as well as 20 km from Sarasota International Convention Center.

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

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.

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.

Edgemere

Siesta Key
Central location

Situated 16 km from The John And Mable Ringling Museum Of Art and 18 km from Sarasota International Convention Center in Siesta Key, Edgemere offers accommodation with a kitchen.

Enjoy breakfast in Siesta Key and nearby

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...

Surf's Up

Siesta Key
Breakfast options

Featuring air-conditioned accommodation with a private pool, Surf's Up is located in Siesta Key. This property offers access to a balcony, free private parking and free WiFi.

Located in Siesta Key, 2.2 km from Siesta Key Beach and 16 km from The John And Mable Ringling Museum Of Art, New Listing! Spacious, 100 percent Private, near the Siesta Key Beach and Village!

Blue Wave

Siesta Key
Breakfast options

Boasting air-conditioned accommodation with a private pool, Blue Wave is situated in Siesta Key. This property offers access to a balcony, free private parking and free WiFi.

Set in Siesta Key, Cape Aqua Retreat offers accommodation with private pool, free WiFi and free private parking for guests who drive.

Casa Blanca

Siesta Key
Breakfast options

Boasting accommodation with a private pool, pool view and a balcony, Casa Blanca is set in Siesta Key. A sauna is available for guests.

Crescent Royale Condominiums 515, a property with massage services, is located in Siesta Key, 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art, as...

Crescent Royale Condominiums 105, a property with massage services, is set in Siesta Key, 18 km from John And Mable Ringling Museum Of Art, 18 km from The John And Mable Ringling Museum Of Art, as...

FAQ about holiday homes in Siesta Key

Holiday homes that guests love in Siesta Key

See all
Scored out of 10, guest rating 7.9
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$441.60
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 197 reviews
Very clean.. close to the main beaches and it is comfortable...
Guest review by
José Roberto
Family with young children