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Our top choices for Siesta Key holiday rentals

1. Tropical Beach Resorts
Tropical Beach ResortsSouth Village
9.4 out of 10, Exceptional, (6,035 reviews)
The price is €181
includes taxes & fees
29 Nov - 30 Nov

2. SeaSpray Resort
SeaSpray ResortSiesta Key
9.6 out of 10, Exceptional, (206 reviews)
The price is €225
includes taxes & fees
8 Nov - 9 Nov

3. Tiny House Siesta
Tiny House SiestaSarasota
8.4 out of 10, Very good, (391 reviews)
The price is €182
includes taxes & fees
2 Dec - 3 Dec

4. Hibiscus Suites - Gateway to Siesta Key
Hibiscus Suites - Gateway to Siesta KeySarasota
8.8 out of 10, Excellent, (2,479 reviews)
The price is €135
includes taxes & fees
19 Nov - 20 Nov

5. Captiva Beach Resort
Captiva Beach ResortSouth Village
9.0 out of 10, Wonderful, (1,332 reviews)
The price is €170
includes taxes & fees
9 Nov - 10 Nov

6. Beach Tree Cottage,Walk To Beach& Siesta
Beach Tree Cottage,Walk To Beach& SiestaSiesta Key Village
The price is €327
includes taxes & fees
6 Nov - 7 Nov

7. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily RentalsSouth Village
9.6 out of 10, Exceptional, (49 reviews)
The price is €266
includes taxes & fees
8 Nov - 9 Nov

8. PinkMango Cottage Steps to Beach&Village
PinkMango Cottage Steps to Beach&VillageSiesta Key Village

9. Beach View 100ft To Beach and SPA
Beach View 100ft To Beach and SPASiesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is €378
includes taxes & fees
11 Nov - 12 Nov

10. Siesta Key, Sea Horse Villa, Pool. Daily rentals
Siesta Key, Sea Horse Villa, Pool. Daily rentalsSouth Village
9.4 out of 10, Exceptional, (55 reviews)
The price is €278
includes taxes & fees
7 Nov - 8 Nov

11. Tiny House Calypso with 1st floor sleeping
Tiny House Calypso with 1st floor sleepingSarasota
9.0 out of 10, Wonderful, (11 reviews)
The price is €155
includes taxes & fees
6 Nov - 7 Nov

12. Siesta Heron Suites & Villas
Siesta Heron Suites & VillasSiesta Key
8.4 out of 10, Very good, (46 reviews)
The price is €280
includes taxes & fees
9 Nov - 10 Nov

13. [lounge like locals] walk to siesta beach +bikes
[lounge like locals] walk to siesta beach +bikesSiesta Key
9.8 out of 10, Exceptional, (37 reviews)
The price is €272
includes taxes & fees
8 Nov - 9 Nov

14. Island Villa | Cozy Beach Retreat | Walk to Village
Island Villa | Cozy Beach Retreat | Walk to VillageSiesta Key Village
8.4 out of 10, Very good, (15 reviews)

15. Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village-Suite #3: A Block to the Beach!Siesta Key Village
9.2 out of 10, Wonderful, (79 reviews)
The price is €359
includes taxes & fees
11 Nov - 12 Nov

16. [Beach Elements] pool view withprivate beach access
[Beach Elements] pool view withprivate beach accessSiesta Key
9.6 out of 10, Exceptional, (45 reviews)
The price is €230
includes taxes & fees
9 Nov - 10 Nov

17. Studio Retreat Across the Street from Beautiful Siesta Key Beach
Studio Retreat Across the Street from Beautiful Siesta Key BeachSiesta Key
9.0 out of 10, Wonderful, (169 reviews)
The price is €281
includes taxes & fees
16 Nov - 17 Nov

18. BlueDolphin Cottage Walk To Siesta Beach
BlueDolphin Cottage Walk To Siesta BeachSiesta Key Village
The price is €364
includes taxes & fees
9 Nov - 10 Nov

19. Tiny House Green Lifeguard Stand - sleeps 5
Tiny House Green Lifeguard Stand - sleeps 5Sarasota
9.4 out of 10, Exceptional, (33 reviews)
The price is €165
includes taxes & fees
6 Nov - 7 Nov

20. Yellow Palm Cottage, Heart of Siesta Key
Yellow Palm Cottage, Heart of Siesta KeySiesta Key Village
The price is €405
includes taxes & fees
9 Nov - 10 Nov
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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