A marina with docked boats, a wooden bridge, and a building with a red roof.

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Osprey holiday homes

Beach

1. Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
The price is HK$1,568
HK$3,454 total
includes taxes & fees
8 Sept - 9 Sept
Charming Osprey Home
Living area

2. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is HK$752
HK$2,427 total
includes taxes & fees
9 Sept - 10 Sept
Siesta Heron Suites & Villas
Private kitchen

3. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is HK$809
HK$2,554 total
includes taxes & fees
7 Sept - 8 Sept
Siesta Key Island Rentals
Pool

4. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (19 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is HK$823
HK$1,939 total
includes taxes & fees
7 Sept - 8 Sept
The Dolphin
Beach

5. Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Siesta Key
9.2 out of 10, Wonderful, (38 reviews)
"Very nice, clean and quiet place."
United States
Monika Z.
The price is HK$1,692
HK$3,409 total
includes taxes & fees
29 Sept - 30 Sept
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Beach

6. Dream Home at Sarasota Gulf Estates Heated pool

Dream Home at Sarasota Gulf Estates Heated pool
Sarasota
9.8 out of 10, Exceptional, (39 reviews)
"Very clean, nice communicative hosts, you can tell they love that place there are a lot of cute personal touches. I felt safe here and it was quiet."
United States
jennifer w.
The price is HK$1,411
HK$3,967 total
includes taxes & fees
7 Sept - 8 Sept
Dream Home at Sarasota Gulf Estates Heated pool
Private kitchen

7. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
The price is HK$541
HK$2,137 total
includes taxes & fees
7 Sept - 8 Sept
[lounge like locals] walk to siesta beach +bikes
Pool

8. Oceanfront home w/sunset views of Sarasota Bay

Oceanfront home w/sunset views of Sarasota Bay
Vamo
9.8 out of 10, Exceptional, (133 reviews)
"Excellent place to stay"
United States
Bob E.
The price is HK$2,972
HK$5,718 total
includes taxes & fees
19 Sept - 20 Sept
Oceanfront home w/sunset views of Sarasota Bay
Private kitchen

9. Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (84 reviews)
"Her stay was outstanding everything was so professionally ready for us we felt at home comfortable the Privacy was impeccable"
United States
James W.
The price is HK$572
HK$1,965 total
includes taxes & fees
7 Sept - 8 Sept
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Interior

10. 3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!

3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
Gulf Gate Estates
10.0 out of 10, Exceptional, (25 reviews)
"Family had a great vacation at this property in Gulf Gate. Very nice pool and deck area and comfortable and clean home, great location for Siesta and Turtle beaches. Host was responsive and a pleasure to deal with, check in/out very simple. We were happy with our stay. "
United States
Martin F.
The price is HK$1,639
HK$4,991 total
includes taxes & fees
7 Sept - 8 Sept
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
Outdoor dining

11. Dolphin Villa - Pool - Steps to Siesta Key Village

Dolphin Villa - Pool - Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "
United States
Sandra C.
The price is HK$721
HK$2,704 total
includes taxes & fees
7 Sept - 8 Sept
Dolphin Villa - Pool - Steps to Siesta Key Village
Dining

12. Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly

Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly
Sarasota Springs
10.0 out of 10, Exceptional, (14 reviews)
"Host is really friendly n helpful!! Loved our stay and would definitely stay again "
United States
Kathryn K.
The price is HK$670
HK$2,627 total
includes taxes & fees
12 Sept - 13 Sept
Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly
Beach

13. Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
Nokomis
10.0 out of 10, Exceptional, (18 reviews)
"Great place close to beach and great food restaurants "
United States
Adan M.
The price is HK$1,188
HK$2,941 total
includes taxes & fees
10 Sept - 11 Sept
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
Beach

14. Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille

Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
Nokomis
10.0 out of 10, Exceptional, (46 reviews)
"Great spot close to many attractions. Very well appointed with all that you need for a great vacation!"
United States
Suzanne G.
The price is HK$1,444
HK$3,337 total
includes taxes & fees
7 Sept - 8 Sept
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
Living area

15. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (218 reviews)
"The host was very communicative and responsive. The pool was a big hit for our family. Comfy beds and a convenient drive to the beach and other venues. Would definitely stay here again. "
United States
Jennifer M.
The price is HK$953
HK$3,663 total
includes taxes & fees
8 Sept - 9 Sept
Siesta beach....one and only
Beach

16. Poolside Paradise Near Siesta Key Beach

Poolside Paradise Near Siesta Key Beach
Bee Ridge
8.8 out of 10, Excellent, (12 reviews)
"Our family of 11 had a truly wonderful stay. The pool was most definitely a highlight."
United States
Fannie Marie S.
The price is HK$1,729
HK$3,675 total
includes taxes & fees
7 Sept - 8 Sept
Poolside Paradise Near Siesta Key Beach
Outdoor dining

17. Gulf Villa - 3 min to #1 Beach - Pool

Gulf Villa - 3 min to #1 Beach - Pool
Siesta Key Village
9.0 out of 10, Wonderful, (17 reviews)
"Nice place to stay."
United States
Ruben C.
The price is HK$992
HK$3,318 total
includes taxes & fees
7 Sept - 8 Sept
Gulf Villa - 3 min to #1 Beach - Pool
Beach

18. Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
South Village
9.6 out of 10, Exceptional, (72 reviews)
"It was very clean and close to the beach. Perfect location."
United States
Cortney
The price is HK$1,685
HK$4,673 total
includes taxes & fees
7 Sept - 8 Sept
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
Beach

19. 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, (22 reviews)
"Great location to walk to siesta key village. "
United States
N A.
The price is HK$1,111
HK$4,772 total
includes taxes & fees
8 Sept - 9 Sept
Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
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 Osprey Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"All great"
Lilian 1-night trip
Posted 3 hours ago
Kompose Boutique Hotel

Find out more about Osprey

Osprey Vacation Homes information

Number of reviews
46
Accommodation
3956 Vacation Homes
Lowest Price
HK$2,427
Highest Price
HK$4,704

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