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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Osprey vacation homes

An aerial view of a beach with a large number of people, a clear blue sky, and a calm sea. There are buildings and palm trees visible in the foreground.

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.
Charming Osprey Home
An aerial view of a beach with a large number of people, a clear blue sky, and a calm sea. There are buildings and palm trees in the foreground.

2. Sunny Coastal Escape

Sunny Coastal Escape
Bay Acres
10.0 out of 10, Exceptional, (6 reviews)
"We were centerally located and had an easy drive to the beach and park. "
United States
Jennifer A.
Sunny Coastal Escape
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.

3. 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 292
AED 1,068 total
includes taxes & fees
30 Oct - 31 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.

4. 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 1,098
AED 2,427 total
includes taxes & fees
20 Nov - 21 Nov
Oceanfront home
A dining table set with plates, glasses, and a decorative glass holder.

5. 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.
Beachside Bliss: Family House-Siesta Key-3BR/2BA
A beach with tall grasses and a sunset.

6. 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 991
AED 1,869 total
includes taxes & fees
6 Nov - 7 Nov
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

7. 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
Sea Turtle- Full Sized living at Tiny House Siesta
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

8. 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 1,225 total
includes taxes & fees
30 Oct - 31 Oct
The Dolphin
A modern kitchen with a built-in washer and dryer, a dining area with a wooden table, and a living room with a sofa and a yellow armchair.

9. Updated Beach House. Walk to Beach, Shop, Waterfront Dining 2 Bed 1 Bath

Updated Beach House. Walk to Beach, Shop, Waterfront Dining 2 Bed 1 Bath
Nokomis
10.0 out of 10, Exceptional, (10 reviews)
"Great stay, good location, attentive host!"
United States
Ashley E.
Updated Beach House. Walk to Beach, Shop, Waterfront Dining 2 Bed 1 Bath
A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

10. 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 320
AED 642 total
includes taxes & fees
1 Nov - 2 Nov
The Mermaid at Tiny House Siesta
A sandy beach with a clear sky and palm trees.

11. 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 737
AED 2,521 total
includes taxes & fees
30 Oct - 31 Oct
FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

12. 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 1,363 total
includes taxes & fees
31 Oct - 1 Nov
Dolphin Villa | Pool | Steps to Siesta Key Village
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

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)
"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 1,321 total
includes taxes & fees
1 Nov - 2 Nov
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

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 AED 677
AED 1,563 total
includes taxes & fees
30 Oct - 31 Oct
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
A cozy outdoor seating area with a fire pit, wicker furniture, and a view into the house.

15. 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.
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
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 284
AED 1,057 total
includes taxes & fees
1 Nov - 2 Nov
[lounge like locals] walk to siesta beach +bikes
An aerial view of a beach with clear skies, a sandy shore, and a mix of greenery and paths.

17. 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
30 Oct - 31 Oct
Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
A beach with a sunset and ocean.

18. Tropical Paradise - Private Saltwater Pool - 5 Min to Siesta Key

Tropical Paradise - Private Saltwater Pool - 5 Min to Siesta Key
Sarasota
10.0 out of 10, Exceptional, (83 reviews)
"The host was extremely responsive and made our stay very enjoyable. Everything was wonderful!"
United States
Kerrianne D.
Tropical Paradise - Private Saltwater Pool - 5 Min to Siesta Key
A narrow hallway leading to a bathroom with a vanity, shelves with storage bins, and a chandelier.

19. Cozy 1-bedroom private room in Sarasota.

Cozy 1-bedroom private room in Sarasota.
Sarasota Springs
10.0 out of 10, Exceptional, (8 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
8 Nov - 9 Nov
Cozy 1-bedroom private room in Sarasota.
A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

20. 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
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
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

Carlisle Inn

Carlisle Inn

10/10 Excellent
"The staff is very friendly. The breakfast is awesome! The rooms are clean and spacious."
Deron 6-night trip
Posted less than an hour ago
Carlisle Inn