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

Search Vacation Homes in Osprey

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Osprey vacation homes

A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

1. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is AED 401
AED 1,192 total
includes taxes & fees
26 Oct - 27 Oct
Siesta Heron Suites & Villas
A modern kitchen with a stainless steel sink, a dining area with a table and chairs, and a living room with a sofa and a TV.

2. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (94 reviews)
"It looks just like the pictures and the sunset daily is absolutely gorgeous. The neighborhood is nice and the people are kind. We loved being short car rides away from stores, beaches and the legacy trail. The owners had great communication. Would definitely stay again."
United States
Ashley H.
The price is AED 970
AED 2,296 total
includes taxes & fees
28 Oct - 29 Oct
Oceanfront home
A dining table set with plates, glasses, and a decorative glass holder.

3. Beachside Bliss: Family House-Siesta Key-3BR/2BA

Beachside Bliss: Family House-Siesta Key-3BR/2BA
Sarasota
10.0 out of 10, Exceptional, (28 reviews)
"Very clean and tucked away in a quiet little neighborhood with everything you need within 10 mins...this place made for the most comfortable and perfect vacation!"
United States
christy v.
The price is AED 370
AED 1,256 total
includes taxes & fees
29 Oct - 30 Oct
Beachside Bliss: Family House-Siesta Key-3BR/2BA
A beach with tall grasses and a sunset.

4. 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)
"This is a beautiful place."
United States
Pam J.
The price is AED 853
AED 1,695 total
includes taxes & fees
26 Oct - 27 Oct
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

5. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (21 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is AED 643
AED 1,236 total
includes taxes & fees
24 Oct - 25 Oct
The Dolphin
A sandy beach with a clear sky and palm trees.

6. FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West
South Village
9.2 out of 10, Wonderful, (7 reviews)
"We had an incredible stay and this is such a great option IN siesta Key that is close to the beaches, has private beach access and is a stand alone building. The unit also has an outdoor shower which was such a great surprise. We will be back!"
United States
Amber M.
The price is AED 581
AED 2,476 total
includes taxes & fees
24 Oct - 25 Oct
FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West
A beach with waves and a bird flying near the shore.

7. The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Traveled with my kids and this place was so great! Super cute and comfortable. We loved the Mermaid Tiny House."
United States
Kadina A.
The price is AED 323
AED 646 total
includes taxes & fees
26 Oct - 27 Oct
The Mermaid at Tiny House Siesta
A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

8. Sea Turtle- Full Sized living at Tiny House Siesta

Sea Turtle- Full Sized living at Tiny House Siesta
Sarasota
9.4 out of 10, Exceptional, (18 reviews)
"The Tiny House is a perfect location to explore Siesta Key and the surrounding areas. It had just what we needed but was in close proximity (walking distance) to many bars and restaurants but was still exceptionally quiet."
United States
Wayne
The price is AED 375
AED 704 total
includes taxes & fees
25 Oct - 26 Oct
Sea Turtle- Full Sized living at Tiny House Siesta
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

9. 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)
"The property was immaculate and inviting! The beds provided great comfort, and the air conditioning was just right. The house was well-equipped, with beach items being a fantastic bonus. The location is unbeatable, and the beach itself was stunning. Highly recommend—10/10!"
United States
Kimberly K.
The price is AED 516
AED 1,277 total
includes taxes & fees
25 Oct - 26 Oct
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

10. 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 AED 677
AED 1,626 total
includes taxes & fees
24 Oct - 25 Oct
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

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)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is AED 422
AED 1,374 total
includes taxes & fees
31 Oct - 1 Nov
Dolphin Villa | Pool | Steps to Siesta Key Village
A cozy outdoor seating area with a fire pit, wicker furniture, and a view into the house.

12. 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, (27 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 AED 852
AED 2,441 total
includes taxes & fees
3 Nov - 4 Nov
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
An aerial view of a beach with clear skies, a sandy shore, and a mix of greenery and paths.

13. 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)
"Beautiful little place. Super clean. Has everything you need. Great communication and quick response to any need. Fast walk to the beach and village."
United States
Ivette R.
The price is AED 521
AED 2,217 total
includes taxes & fees
24 Oct - 25 Oct
Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
A beach with clear blue water and a sandy shore.

14. "The Lobster" at The Shore Beach Houses Resort

"The Lobster" at The Shore Beach Houses Resort
Nokomis
10.0 out of 10, Exceptional, (3 reviews)
"Thanks so much, great space and location! Would love to come back. "
United States
Ashley
The price is AED 1,084
AED 1,962 total
includes taxes & fees
31 Oct - 1 Nov
"The Lobster" at The Shore Beach Houses Resort
A clear swimming pool with a pink float, surrounded by a covered area with chairs and a wooden fence.

15. Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Ridge Wood Heights
9.4 out of 10, Exceptional, (128 reviews)
"Beautiful home, perfect location! Would come back again. Thank you!!! "
United States
Joe V.
The price is AED 569
AED 1,040 total
includes taxes & fees
25 Oct - 26 Oct
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

16. [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)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
The price is AED 340
AED 1,138 total
includes taxes & fees
25 Oct - 26 Oct
[lounge like locals] walk to siesta beach +bikes
A lifeguard tower with a red exterior, a flagpole with an American flag, and a beach with people and buildings in the background.

17. Poolside Paradise Near Siesta Key Beach

Poolside Paradise Near Siesta Key Beach
Bee Ridge
8.8 out of 10, Excellent, (13 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 AED 731
AED 1,595 total
includes taxes & fees
25 Oct - 26 Oct
Poolside Paradise Near Siesta Key Beach
A narrow hallway leading to a bathroom with a vanity, shelves with storage bins, and a chandelier.

18. Cozy 1-bedroom private room in Sarasota.

Cozy 1-bedroom private room in Sarasota.
Sarasota Springs
10.0 out of 10, Exceptional, (7 reviews)
"Great 1 bedroom/1 bath in a quiet neighborhood. Friendly host. Accommodations were very accurately described. There is a mini fridge which was a nice convenience to have."
United States
Larry H.
The price is AED 184
AED 447 total
includes taxes & fees
29 Oct - 30 Oct
Cozy 1-bedroom private room in Sarasota.
A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

19. Island Villa | Cozy Beach Retreat | Walk to Village

Island Villa | Cozy Beach Retreat | Walk to Village
Siesta Key Village
8.4 out of 10, Very good, (14 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is AED 338
AED 1,381 total
includes taxes & fees
25 Oct - 26 Oct
Island Villa | Cozy Beach Retreat | Walk to Village
An aerial view of a beach with clear skies, a sandy shore, and a mix of greenery and paths.

20. Pet Friendly home, Close to Sarasota Beach!

Pet Friendly home, Close to Sarasota Beach!
Siesta Key Village
9.0 out of 10, Wonderful, (8 reviews)
"Great house great location will definitely come back to this property "
United States
Matthew Y.
The price is AED 614
AED 2,337 total
includes taxes & fees
24 Oct - 25 Oct
Pet Friendly home, Close to Sarasota Beach!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

8/10 Good
"The property was nice. It would have been better if the hot tub was in working condition."
Rebecca 2-night trip
Posted 2 hours ago
Spark by Hilton Sarasota Siesta Key Gateway