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 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 356
AED 1,141 total
includes taxes & fees
8 Oct - 9 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, (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.
The price is AED 973
AED 2,285 total
includes taxes & fees
12 Oct - 13 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)
"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.
The price is AED 364
AED 1,260 total
includes taxes & fees
15 Oct - 16 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 813
AED 1,623 total
includes taxes & fees
8 Oct - 9 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.

5. 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.
The price is AED 808
AED 2,092 total
includes taxes & fees
23 Oct - 24 Oct
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
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
8 Oct - 9 Oct
The Pelican
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 320
AED 642 total
includes taxes & fees
12 Oct - 13 Oct
The Mermaid at Tiny House Siesta
A covered patio with a round table and chairs, large windows, and a view of a backyard with a wooden fence and palm trees.

8. 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 1,233 total
includes taxes & fees
18 Oct - 19 Oct
2 miles to #1 Beach Siesta Key
A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

9. 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 712 total
includes taxes & fees
21 Oct - 22 Oct
Sea Turtle- Full Sized living at Tiny House Siesta
A cozy outdoor seating area with a fire pit, wicker furniture, and a view into the house.

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, (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 856
AED 2,452 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 beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

11. 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 AED 516
AED 1,266 total
includes taxes & fees
8 Oct - 9 Oct
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
A narrow hallway leading to a bathroom with a vanity, shelves with storage bins, and a chandelier.

12. Cozy 1-bedroom private room in Sarasota.

Cozy 1-bedroom private room in Sarasota.
Sarasota Springs
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 184
AED 447 total
includes taxes & fees
12 Oct - 13 Oct
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.

13. 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 789
AED 2,171 total
includes taxes & fees
8 Oct - 9 Oct
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

14. [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
8 Oct - 9 Oct
[lounge like locals] walk to siesta beach +bikes
A beach path leading to the ocean with a signpost.

15. Cozy Beach House Just Minutes From Siesta Key

Cozy Beach House Just Minutes From Siesta Key
Sarasota
9.0 out of 10, Wonderful, (18 reviews)
"Loved it"
United States
MIRIAM
The price is AED 598
AED 1,230 total
includes taxes & fees
21 Oct - 22 Oct
Cozy Beach House Just Minutes From Siesta Key
A clear swimming pool with a pink float, surrounded by a covered area with chairs and a wooden fence.

16. 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, (127 reviews)
"Barb was very helpful and made numerous quality suggestions for nearby restaurants and activities."
United States
Mitzy B.
The price is AED 569
AED 1,011 total
includes taxes & fees
21 Oct - 22 Oct
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
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, (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 AED 633
AED 1,459 total
includes taxes & fees
21 Oct - 22 Oct
Poolside Paradise Near Siesta Key Beach
A wooden dock extending over calm water, surrounded by lush greenery and palm trees.

18. Walk to the Beach | Osprey Villa | Siesta Key

Walk to the Beach | Osprey Villa | Siesta Key
Siesta Key Village
9.8 out of 10, Exceptional, (21 reviews)
"Host was very helpful. The apt was very comfy"
United States
Barbara B.
The price is AED 334
AED 1,171 total
includes taxes & fees
8 Oct - 9 Oct
Walk to the Beach | Osprey Villa | Siesta Key
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

19. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (219 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 AED 446
AED 1,716 total
includes taxes & fees
9 Oct - 10 Oct
Siesta beach....one and only
A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

20. 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 422
AED 1,488 total
includes taxes & fees
12 Oct - 13 Oct
Island Villa | Cozy Beach Retreat | Walk to Village
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"Nice and easy access to store, restaurant etc"
Sunday 5-night trip
Posted 16 hours ago
Spark by Hilton Sarasota Siesta Key Gateway