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Find vacation rentals that suit your style

Apartments

Aparthotels
Our top choices for Osprey apartments

1. Casey Key Resort
Casey Key ResortCasey Key
8.4 out of 10, Very good, (287 reviews)
$215 nightly
The price is $240
Dec 2 - Dec 3
Total with taxes and fees

2. 2 Bedroom/2 Bath Villa (Second Level) - Unit 14/D
2 Bedroom/2 Bath Villa (Second Level) - Unit 14/DCasey Key
10.0 out of 10, Exceptional, (1 review)
$302 nightly
The price is $339
Nov 30 - Dec 1
Total with taxes and fees

3. 2 Miles to Siesta Key
2 Miles to Siesta KeyGulf Gate Estates
10.0 out of 10, Exceptional, (29 reviews)
$157 nightly
The price is $176
Nov 11 - Nov 12
Total with taxes and fees

4. Bright & Beachy–Beach Club Siesta Key 100A by RVA
Bright & Beachy–Beach Club Siesta Key 100A by RVASouth Village
9.0 out of 10, Wonderful, (119 reviews)
$284 nightly
The price is $319
Dec 4 - Dec 5
Total with taxes and fees

5. Tiny House Calypso with 1st floor sleeping
Tiny House Calypso with 1st floor sleepingSarasota
9.0 out of 10, Wonderful, (11 reviews)
$151 nightly
The price is $170
Nov 10 - Nov 11
Total with taxes and fees

6. Tiny House Seashell - tiny living at the beach
Tiny House Seashell - tiny living at the beachSarasota
8.6 out of 10, Excellent, (10 reviews)
$140 nightly
The price is $157
Nov 10 - Nov 11
Total with taxes and fees

7. 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)
$246 nightly
The price is $276
Nov 10 - Nov 11
Total with taxes and fees

8. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.South Village
9.8 out of 10, Exceptional, (34 reviews)
$191 nightly
The price is $214
Nov 10 - Nov 11
Total with taxes and fees

9. VILLA 4, Siesta Key, Walk to Beach. Pool. Daily Rentals
VILLA 4, Siesta Key, Walk to Beach. Pool. Daily RentalsSarasota
9.4 out of 10, Exceptional, (50 reviews)
$257 nightly
The price is $289
Nov 10 - Nov 11
Total with taxes and fees

10. [Sunny in Siesta] king bed + walk to beach
[Sunny in Siesta] king bed + walk to beachSouth Village
9.6 out of 10, Exceptional, (15 reviews)
$286 nightly
The price is $293
Nov 12 - Nov 13
Total with taxes and fees

11. Tiny House Yellow Lifeguard Stand- pet friendly
Tiny House Yellow Lifeguard Stand- pet friendlySarasota
9.4 out of 10, Exceptional, (51 reviews)
$153 nightly
The price is $172
Nov 10 - Nov 11
Total with taxes and fees

12. Tiny House Green Lifeguard Stand - sleeps 5
Tiny House Green Lifeguard Stand - sleeps 5Sarasota
9.4 out of 10, Exceptional, (33 reviews)
$160 nightly
The price is $180
Nov 10 - Nov 11
Total with taxes and fees

13. VILLA 3 · Pool view. Walk to beach. Daily rentals
VILLA 3 · Pool view. Walk to beach. Daily rentalsSarasota
9.6 out of 10, Exceptional, (47 reviews)
$257 nightly
The price is $289
Nov 10 - Nov 11
Total with taxes and fees

14. Beachside Bliss- 1 mi to the beach w/ heated pool
Beachside Bliss- 1 mi to the beach w/ heated poolSarasota
9.0 out of 10, Wonderful, (7 reviews)
$235 nightly
The price is $264
Nov 10 - Nov 11
Total with taxes and fees

15. Red Lifeguard Stand - pet freindly
Red Lifeguard Stand - pet freindlySarasota
9.4 out of 10, Exceptional, (26 reviews)
$158 nightly
The price is $177
Nov 10 - Nov 11
Total with taxes and fees

16. Tiny House Margarita - Sleeps 6
Tiny House Margarita - Sleeps 6Sarasota
8.4 out of 10, Very good, (11 reviews)
$151 nightly
The price is $170
Nov 10 - Nov 11
Total with taxes and fees

17. [Beach Retreat] modern condo +5 min. walk to beach
[Beach Retreat] modern condo +5 min. walk to beachSouth Village
9.4 out of 10, Exceptional, (6 reviews)
$260 nightly
The price is $265
Nov 10 - Nov 11
Total with taxes and fees

18. Private Studio · Near Siesta Key · Pet-Friendly
Private Studio · Near Siesta Key · Pet-FriendlySouth Gate Ridge
9.0 out of 10, Wonderful, (17 reviews)
$148 nightly
The price is $166
Nov 17 - Nov 18
Total with taxes and fees

19. Literally 3 mins from Siesta with its number 1 beaches!!!! Location! Location!
Literally 3 mins from Siesta with its number 1 beaches!!!! Location! Location!Sarasota
10.0 out of 10, Exceptional, (5 reviews)
$519 nightly
The price is $580
Nov 10 - Nov 11
Total with taxes and fees

20. Spacious 2BR/2BA Garden Condo w/ Heated Pool
Spacious 2BR/2BA Garden Condo w/ Heated PoolSarasota
9.2 out of 10, Wonderful, (17 reviews)
$313 nightly
The price is $352
Nov 10 - Nov 11
Total with taxes and fees
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.
Learn more about Osprey
Paddle through Oscar Scherer State Park's serene waterways where you might spot eagles, turtles, and alligators along the way. Nearby Sarasota's white-sand beaches and Myakka River State Park offer perfect day trips from this peaceful Gulf Coast community.


































































