Holiday Homes in Siesta Key

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Our top choices for Siesta Key holiday homes

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (54)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
Siesta Key Island Rentals

[Tropical] guesthouse retreat on Siesta Key

[Tropical] guesthouse retreat on Siesta Key
Siesta Key
10.0 out of 10, Exceptional, (1)
"Great. Was very responsive "
United States
Mark B.
The price is €237
includes taxes & fees
22 Dec - 23 Dec
[Tropical] guesthouse retreat on Siesta Key

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is €351
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Heron Suites & Villas

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (25)
"The property was very clean and conveniently located ."
United States
David
The price is €280
includes taxes & fees
25 Dec - 26 Dec
[lounge like locals] walk to siesta beach +bikes

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
2.0 star property
Sarasota
10.0 out of 10, Exceptional, (2)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
The price is €226
includes taxes & fees
22 Dec - 23 Dec
The Mermaid at Tiny House Siesta

Tiny House Blue Lifeguard - pet friendly

Tiny House Blue Lifeguard - pet friendly
Sarasota
7.4 out of 10, Good, (3)
"The process was 100% contactless and easy. The tiny home was cute and clean for the most part but it is in disrepair and needs deep cleaning. There was mold in the shower (like a lot) on the knobs and walls. Also, the floorboards were weak under the bathroom and it felt like it was caving in. (I am not a large or heavy person). One of the pillow covers had a blood stain, and there was a thick layer of dust on the art throughout the unit. The little community was very cute. I’d stay again for...
United States
April S.
The price is €245
includes taxes & fees
22 Dec - 23 Dec
Tiny House Blue Lifeguard - pet friendly

NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS

NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS
South Village
9.4 out of 10, Exceptional, (44)
"Beautiful place close to the beach’s and love it would stay here again "
United States
Steve D.
The price is €229
includes taxes & fees
22 Dec - 23 Dec
NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS

[Relax by the Pool]Siesta Key

[Relax by the Pool]Siesta Key
Siesta Key
9.0 out of 10, Wonderful, (13)
"Awesome little hidden spot close to the beach (literally like 5 min drive).Very clean, private, and great communication with host!! Short family staycation and would definitely do again."
United States
James P.
The price is €406
includes taxes & fees
22 Dec - 23 Dec
[Relax by the Pool]Siesta Key

Walk to Siesta key beach | Private Dock | Patio | Pool

Walk to Siesta key beach | Private Dock | Patio | Pool
Siesta Key Village
9.4 out of 10, Exceptional, (14)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is €361
includes taxes & fees
12 Jan - 13 Jan 2026
Walk to Siesta key beach | Private Dock | Patio | Pool

Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
Siesta Key Village
9.6 out of 10, Exceptional, (17)
"Great location to walk to siesta key village. "
United States
N A.
The price is €512
includes taxes & fees
22 Dec - 23 Dec
Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West
South Village
8.8 out of 10, Excellent, (3)
"Very nice. Walking distance to beach and restaurants"
United States
Mark P.
The price is €529
includes taxes & fees
22 Dec - 23 Dec
FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

Gulf Villa in Siesta Key | Beachfront Vibes & Dock

Gulf Villa in Siesta Key | Beachfront Vibes & Dock
Siesta Key Village
8.8 out of 10, Excellent, (11)
"My absolute favorite place to stay! Clean, friendly and perfect location to the beach and village."
United States
Tisha P.
The price is €511
includes taxes & fees
13 Jan - 14 Jan 2026
Gulf Villa in Siesta Key | Beachfront Vibes & Dock

Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.6 out of 10, Exceptional, (190)
"We had a wonderful time.the host was wonderful .we had a leak in the bathroom and he came right over and fixed in in a matter of minutes .we were very impressed.we would stay there again."
United States
Martha C.
The price is €443
includes taxes & fees
12 Jan - 13 Jan 2026
Siesta beach....one and only

Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool

Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool
Siesta Key Village
8.8 out of 10, Excellent, (12)
"Had a great evening in a location that is conveniently walkable to the best of Siesta Key. Excellent communication from Owner and all amenities were fun and fully functional."
United States
John M.
The price is €429
includes taxes & fees
22 Dec - 23 Dec
Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool

Condo with Private Beach Access, Great Shared Amenities - Private Beach House

Condo with Private Beach Access, Great Shared Amenities - Private Beach House
Siesta Key
9.0 out of 10, Wonderful, (44)
"This rental was in a great area with access to the free trolley. The beach was amazing! I would definitely stay here again."
United States
Renee B.
The price is €693
includes taxes & fees
25 Dec - 26 Dec
Condo with Private Beach Access, Great Shared Amenities - Private Beach House

[Ocean Oasis] guest house on siesta key

[Ocean Oasis] guest house on siesta key
Siesta Key
The price is €207
includes taxes & fees
23 Dec - 24 Dec
[Ocean Oasis] guest house on siesta key

"Safe & Clean" Honeymoon Suite, - only 60 steps to the Siesta Key Public Beach -

"Safe & Clean" Honeymoon Suite, - only 60 steps to the Siesta Key Public Beach -
Siesta Key
9.6 out of 10, Exceptional, (41)
"Beautiful views from both balconies, lots of light and everything you could possibly need and more! Close to beach access and a short walk to the village! We had a lovely time. Thank you so much!"
United States
Sylvie W.
The price is €453
includes taxes & fees
24 Dec - 25 Dec
"Safe & Clean" Honeymoon Suite, - only 60 steps to the Siesta Key Public Beach -

Everglades Villa Near Siesta key beach w/d Private Dock

Everglades Villa Near Siesta key beach w/d Private Dock
Siesta Key Village
9.0 out of 10, Wonderful, (12)
"Great location, clean, good communication. "
United States
Alexandra P.
The price is €451
includes taxes & fees
13 Jan - 14 Jan 2026
Everglades Villa Near Siesta key beach w/d Private Dock

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Siesta Key
9.6 out of 10, Exceptional, (55)
"Great place to stay and enjoy the Beach!"
United States
Matt G.
The price is €667
includes taxes & fees
26 Dec - 27 Dec
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Modern & Bright Escape: Mins Beach, Pool, Hot Tub!

Modern & Bright Escape: Mins Beach, Pool, Hot Tub!
2.0 star property
South Village
The price is €331
includes taxes & fees
12 Jan - 13 Jan 2026
Modern & Bright Escape: Mins Beach, Pool, Hot Tub!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Siesta Key Hotel Reviews

Find out more about Siesta Key

Siesta Key Holiday Homes information

Number of reviews
553
Accommodation
899 Holiday Homes
Lowest Price
€207
Highest Price
€693

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