Search Vacation Homes in Siesta Key

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Our top choices for Siesta Key holiday homes

Holiday Home in Sarasota

The Mermaid at Tiny House Siesta
2.0 star property
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 HK$863
HK$1,569 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Mermaid at Tiny House Siesta

Holiday Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
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 HK$1,417
HK$3,165 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Heron Suites & Villas
10.0 out of 10, Exceptional, (1)
"Great. Was very responsive "
United States
Mark B.
The price is HK$872
HK$2,238 total
includes taxes & fees
6 Jan - 7 Jan 2026
[Tropical] guesthouse retreat on Siesta Key
8.8 out of 10, Excellent, (6)
The price is HK$971
HK$1,523 total
includes taxes & fees
24 Jan - 25 Jan 2026
3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.
9.8 out of 10, Exceptional, (26)
"The property was very clean and conveniently located ."
United States
David
The price is HK$1,113
HK$2,850 total
includes taxes & fees
12 Jan - 13 Jan 2026
[lounge like locals] walk to siesta beach +bikes

Holiday Home in Siesta Key Village

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Lulu's Key House Leatherback 2/2 Downstairs

Holiday Home in Siesta Key Village

Siesta Key Villa w/d Beach Access | Pool & More
9.8 out of 10, Exceptional, (18)
"Great location! Clean and nicely decorated. The property manager was very accommodating and easy to communicate with. "
United States
Danielle G.
The price is HK$1,387
HK$3,283 total
includes taxes & fees
28 Dec - 29 Dec
Siesta Key Villa w/d Beach Access | Pool & More
8.6 out of 10, Excellent, (33)
"Perfectly described and wonderful location. "
United States
Bill K.
The price is HK$971
HK$1,824 total
includes taxes & fees
4 Jan - 5 Jan 2026
2 Bedroom 2 Bath home near Siesta Key Beach
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 HK$1,003
HK$1,982 total
includes taxes & fees
4 Jan - 5 Jan 2026
NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS

Holiday Home in Siesta Key

[Ocean Oasis] guest house on siesta key
The price is HK$640
HK$1,994 total
includes taxes & fees
5 Jan - 6 Jan 2026
[Ocean Oasis] guest house on siesta key

Holiday Home in Siesta Key

[Relax by the Pool]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 HK$1,281
HK$3,715 total
includes taxes & fees
4 Jan - 5 Jan 2026
[Relax by the Pool]Siesta Key

Holiday Home in Sarasota

Siesta beach....one and only
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 HK$1,322
HK$3,876 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta beach....one and only
9.0 out of 10, Wonderful, (12)
"Great location, clean, good communication. "
United States
Alexandra P.
The price is HK$1,582
HK$3,979 total
includes taxes & fees
13 Jan - 14 Jan 2026
Everglades Villa Near Siesta key beach w/d Private Dock

Holiday Home in Siesta Key Village

Gulf Villa in Siesta Key | Beachfront Vibes & Dock
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 HK$2,038
HK$4,483 total
includes taxes & fees
12 Jan - 13 Jan 2026
Gulf Villa in Siesta Key | Beachfront Vibes & Dock
2.0 star property
The price is HK$1,126
HK$2,877 total
includes taxes & fees
8 Jan - 9 Jan 2026
Modern & Bright Escape: Mins Beach, Pool, Hot Tub!
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 HK$3,000
HK$4,949 total
includes taxes & fees
3 Jan - 4 Jan 2026
"Safe & Clean" Honeymoon Suite, - only 60 steps to the Siesta Key Public Beach -
10.0 out of 10, Exceptional, (1)
"Kyle was great to deal with, and the property was amazing . We had an amazing time "
United States
Tiffany K.
The price is HK$34,450
HK$41,571 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Key Village, Heated Pool, Beach Access 4 min Walk, 8bdr
10.0 out of 10, Exceptional, (1)
The price is HK$2,518
HK$5,113 total
includes taxes & fees
9 Jan - 10 Jan 2026
Location! Siesta Beach 1 mile away. Home with Hot Spa.
10.0 out of 10, Exceptional, (2)
"My husband, parents and I only stayed for three nights, but it was an absolute perfect spot for us! Very close to the beach and trolley stops to get you pretty much anywhere on Siesta Key. The place was very clean and adorably decorated. The pool and hot tub were exactly as described and made our trip even better. We Would definitely stay here again!"
United States
Melissa B.
The price is HK$2,448
HK$5,043 total
includes taxes & fees
6 Jan - 7 Jan 2026
2 Bedroom Unit with Pool - 2 min walk to Siesta Beach

Holiday Home in Siesta Key Village

3 Min Walk to Siesta Key Beach | Patio & More
8.2 out of 10, Very good, (12)
"We had a wonderful stay! The location was perfect, and the property was exceptionally clean. The hosts were excellent with communication and always responded promptly. Highly recommend!"
United States
Amy P.
The price is HK$1,528
HK$3,903 total
includes taxes & fees
6 Jan - 7 Jan 2026
3 Min Walk to Siesta Key Beach | Patio & More
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 Vacation Homes information

Number of reviews
438
Accommodation
899 Vacation Homes
Lowest Price
HK$1,523
Highest Price
HK$41,571

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