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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Osprey vacation homes

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.

1. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (93 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.
Oceanfront home
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.

2. 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 368
AED 1,155 total
includes taxes & fees
13 Oct - 14 Oct
Siesta Heron Suites & Villas
A bedroom with a bed, a dresser, a TV, and a window with a view of greenery.

3. 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 845
AED 1,675 total
includes taxes & fees
15 Oct - 16 Oct
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
A modern kitchen with stainless steel appliances, a dining area with a round table and chairs, and a large window overlooking a backyard.

4. KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Gulf Gate Estates
10.0 out of 10, Exceptional, (45 reviews)
"Our 2nd time here and we’ll be back again! Thanks Tim and family for such a great house!"
United States
Angela K.
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
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)
"Great property! Very clean and spacious. Perfect for what we needed and close to Siesta Key and Gulf Gate restaurants and bars,"
United States
Lori B.
Beachside Bliss: Family House-Siesta Key-3BR/2BA
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

6. The Pelican

The Pelican
Nokomis
10.0 out of 10, Exceptional, (8 reviews)
"Everything was great about our stay. Very clean"
United States
MARC G.
The price is AED 826
AED 1,573 total
includes taxes & fees
24 Oct - 25 Oct
The Pelican
A covered patio with a round table and chairs, large windows, and a view of a backyard with a wooden fence and palm trees.

7. 2 miles to #1 Beach Siesta Key

2 miles to #1 Beach Siesta Key
Sarasota
9.8 out of 10, Exceptional, (85 reviews)
"Clean and convenient"
United States
Scott H.
The price is AED 430
AED 1,248 total
includes taxes & fees
18 Oct - 19 Oct
2 miles to #1 Beach Siesta Key
A beach with waves and a bird flying near the shore.

8. 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 433
AED 785 total
includes taxes & fees
24 Oct - 25 Oct
The Mermaid at Tiny House Siesta
A cozy outdoor seating area with a fire pit, wicker furniture, and a view into the house.

9. 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, (26 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 834
AED 2,424 total
includes taxes & fees
11 Oct - 12 Oct
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
A backyard with a swimming pool, patio furniture, and a barbecue grill.

10. Key Life Living l Private Heated Pool & 5 Minute Walk to Crescent Beach

Key Life Living l Private Heated Pool & 5 Minute Walk to Crescent Beach
Siesta Key
9.4 out of 10, Exceptional, (6 reviews)
"Lovely property and excellent communication! Thank you!"
United States
Barbara
The price is AED 2,416
AED 5,606 total
includes taxes & fees
24 Oct - 25 Oct
Key Life Living l Private Heated Pool & 5 Minute Walk to Crescent Beach
A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

11. 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 AED 1,027
AED 2,469 total
includes taxes & fees
11 Oct - 12 Oct
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
A coastal hotel with multiple buildings, a beach, and ocean waves.

12. Key Life Reef l Semi-Private Pool, Walk to the Beach!

Key Life Reef l Semi-Private Pool, Walk to the Beach!
Siesta Key
9.4 out of 10, Exceptional, (8 reviews)
"Exactly what we were looking for. A place near the beach with a pool. Clean, modern, attentive manager. Would recommend highly."
United States
isabel b.
The price is AED 1,208
AED 2,797 total
includes taxes & fees
24 Oct - 25 Oct
Key Life Reef l Semi-Private Pool, Walk to the Beach!
A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

13. 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 489
AED 855 total
includes taxes & fees
24 Oct - 25 Oct
Sea Turtle- Full Sized living at Tiny House Siesta
A modern kitchen with white cabinetry, stainless steel appliances, and a tiled backsplash.

14. Condo with Private Beach Access, Great Shared Amenities - Private Beach House

Condo with Private Beach Access, Great Shared Amenities - Private Beach House
Siesta Key
9.2 out of 10, Wonderful, (50 reviews)
"Our stay at Private Beach House was excellent! The location was perfect, the beach was beautiful, and the house was very comfortable and convenient. We absolutely enjoyed our time there and would definitely stay again. We did have an issue with the water for one night, but we called and they were very responsive and had it resolved in less than an hour. We really appreciated how quickly they took care of it. Overall, we had a wonderful stay and would definitely recommend Private Beach House!"
United States
Kelmarie
The price is AED 732
AED 3,119 total
includes taxes & fees
11 Oct - 12 Oct
Condo with Private Beach Access, Great Shared Amenities - Private Beach House
A beach with a sunset and ocean.

15. 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)
"Very nice place and the neighborhood very quiet"
United States
Ieshia M.
The price is AED 909
AED 2,307 total
includes taxes & fees
24 Oct - 25 Oct
Tropical Paradise - Private Saltwater Pool - 5 Min to Siesta Key
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

16. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (220 reviews)
"Host was very helpful and friendly"
United States
Alexa
The price is AED 459
AED 1,731 total
includes taxes & fees
21 Oct - 22 Oct
Siesta beach....one and only
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

17. 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.
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
A lifeguard tower with a red exterior, a flagpole with an American flag, and a beach with people and buildings in the background.

18. 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 760
AED 1,632 total
includes taxes & fees
12 Oct - 13 Oct
Poolside Paradise Near Siesta Key Beach
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

19. 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
24 Oct - 25 Oct
The Dolphin
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

20. 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
12 Oct - 13 Oct
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
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
"Love staying at the Kompose! Great staff!! Amazing rooms!! Breakfast is 👍👍"
Jacqueline 2-night trip
Posted 8 hours ago
Kompose Boutique Hotel