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

Holiday Homes in Osprey

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Our top choices for Osprey holiday homes

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 NZ$756
includes taxes & fees
8 Sept - 9 Sept
Charming Osprey Home

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 NZ$521
includes taxes & fees
9 Sept - 10 Sept
Siesta Heron Suites & Villas

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 NZ$554
includes taxes & fees
7 Sept - 8 Sept
Siesta Key Island Rentals

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 NZ$419
includes taxes & fees
7 Sept - 8 Sept
The Dolphin

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 NZ$744
includes taxes & fees
28 Sept - 29 Sept
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

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.
Dream Home at Sarasota Gulf Estates Heated pool

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 NZ$475
includes taxes & fees
7 Sept - 8 Sept
[lounge like locals] walk to siesta beach +bikes

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.
Oceanfront home w/sunset views of Sarasota Bay

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 NZ$426
includes taxes & fees
7 Sept - 8 Sept
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

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 NZ$1,079
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!

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 NZ$576
includes taxes & fees
7 Sept - 8 Sept
Dolphin Villa - Pool - Steps to Siesta Key Village

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 NZ$563
includes taxes & fees
12 Sept - 13 Sept
Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly

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 NZ$629
includes taxes & fees
10 Sept - 11 Sept
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

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 NZ$754
includes taxes & fees
7 Sept - 8 Sept
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille

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 NZ$791
includes taxes & fees
8 Sept - 9 Sept
Siesta beach....one and only

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 NZ$815
includes taxes & fees
16 Sept - 17 Sept
Poolside Paradise Near Siesta Key Beach

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 NZ$721
includes taxes & fees
7 Sept - 8 Sept
Gulf Villa - 3 min to #1 Beach - Pool

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 NZ$1,015
includes taxes & fees
7 Sept - 8 Sept
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

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 NZ$1,037
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

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews
676
Accommodation
3972 Holiday Homes
Lowest Price
NZ$419
Highest Price
NZ$1,079