Holiday Homes in Siesta Key
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Our top choices for Siesta Key holiday homes
Holiday Home in Siesta Key
[lounge like locals] walk to siesta beach +bikes9.8 out of 10, Exceptional, (26)
"The property was very clean and conveniently located ."
David
The price is NZ$471
includes taxes & fees
25 Dec - 26 Dec
Holiday Home in Sarasota
The Mermaid at Tiny House Siesta10.0 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."
Jackeline R.
The price is NZ$357
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Siesta Key
Siesta Heron Suites & Villas8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
Jesse
The price is NZ$720
includes taxes & fees
26 Dec - 27 Dec
Holiday Home in Siesta Key
[Tropical] guesthouse retreat on Siesta Key10.0 out of 10, Exceptional, (1)
"Great. Was very responsive "
Mark B.
The price is NZ$493
includes taxes & fees
6 Jan - 7 Jan 2026
Holiday Home in Siesta Key Village
Lulu's Key House Leatherback 2/2 DownstairsThe price is NZ$1,024
includes taxes & fees
27 Dec - 28 Dec
Holiday Home in Siesta Key Village
Siesta Key Villa w/d Beach Access | Pool & More9.8 out of 10, Exceptional, (18)
"Great location! Clean and nicely decorated. The property manager was very accommodating and easy to communicate with. "
Danielle G.
The price is NZ$699
includes taxes & fees
12 Jan - 13 Jan 2026
Holiday Home in Sarasota
2 Bedroom 2 Bath home near Siesta Key Beach8.6 out of 10, Excellent, (33)
"This place was very comfortable, and a great location, close to everything we needed. Check in/out was a breeze.Will keep this on our saved list for next time."
Michael C.
The price is NZ$402
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Siesta Key
[Ocean Oasis] guest house on siesta keyThe price is NZ$439
includes taxes & fees
5 Jan - 6 Jan 2026
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.
Top Siesta Key Hotel Reviews
The Ringling Beach House
10/10 Excellent
Find out more about Siesta Key
Siesta Key Holiday Homes information
Number of reviews | 482 |
|---|---|
Accommodation | 899 Holiday Homes |
Lowest Price | NZ$357 |
Highest Price | NZ$1,987 |
Explore a world of travel with Expedia
- Resort in Osprey
- Country House in Anna Maria Island
- Inns in Anna Maria Island
- Motels in Sarasota
- Cottages in Sarasota
- Apartments in Sarasota
- B&B in Sarasota
- Motels in Siesta Key
- Cottages in Siesta Key
- Apartments in Siesta Key
- Condo Rentals in Siesta Key
- Guest Houses in Siesta Key
- Villas in Siesta Key
- Resort in Siesta Key
- Villas in Casey Key
- Inns in Casey Key
- Lodges in Casey Key
- Holiday Homes in Longboat Key
- Condo Rentals in Venice
- Motels in Venice
- Holiday Homes in Bradenton Beach
- Holiday Homes in Lido Key
- Caravan Parks in Lido Key
- Apartments in Bradenton
- Condo Rentals in Holmes Beach
- Guest Houses in Legacy Trail
- Villas in Legacy Trail
- Villas in Island of Venice
- Guest Houses in Island of Venice
- B&B in Island of Venice
- Casino Hotels in Siesta Key
- Pet Friendly Hotels in Siesta Key
- Boutique Hotels in Siesta Key
- Luxury Hotels in Siesta Key
- Romantic Hotels in Siesta Key
- Cheap Hotels in Siesta Key
- Beach Hotels in Siesta Key
- All Inclusive Hotels in Siesta Key
- Lgbt Welcoming Hotels in Central Sarasota
- Cheap Hotels in Sarasota
- Beach Hotels in Sarasota
- Boutique Hotels in Sarasota
- Family Hotels in Siesta Key Village
- Beach Hotels in Lido Key
- Luxury Hotels in Lido Key
- Lgbt Welcoming Hotels in South Sarasota
- Hotels near Ed Smith Stadium
- Southgate Hotels
- South Gate Ridge Hotels
- South Sarasota Hotels
- Hotels near Stoneybrook Golf & Country Club
- Hotels near St. Armands Circle
- Vamo Hotels
- Hotels near Ringling College of Art and Design
- Hotels near Turtle Beach
- Hotels near Sarasota Opera House
- Central Sarasota Hotels
- Hotels near Siesta Key Beach
- Siesta Key Hotels
- Hotels near Historic Spanish Point
- Siesta Key Village Hotels
- Palmer Ranch Hotels
- Downtown Sarasota Hotels
- Pinecraft Hotels
- Aloha Kai Hotels
- Hotels near Sarasota Memorial Hospital
- Sarasota Hotels
- Bayview Hotels