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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Osprey vacation homes

House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

1. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, 45, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is AED 309
AED 1,088 total
includes taxes & fees
15 Sep - 16 Sep
Siesta Heron Suites & Villas
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

2. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.4 out of 10, 81, (81 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is AED 369
AED 1,185 total
includes taxes & fees
15 Sep - 16 Sep
Siesta Key Island Rentals
Outdoor pool, a heated pool

3. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, 21, (21 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is AED 386
AED 875 total
includes taxes & fees
20 Sep - 21 Sep
The Dolphin
Interior

4. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, 93, (93 reviews)
"Loved the house. It had everything you could possibly need"
United States
Erin G.
Oceanfront home
Beach

5. The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, 4, (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 404
AED 741 total
includes taxes & fees
20 Sep - 21 Sep
The Mermaid at Tiny House Siesta
Coffee/tea maker, fridge, microwave, oven

6. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, 37, (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 AED 295
AED 1,042 total
includes taxes & fees
16 Sep - 17 Sep
[lounge like locals] walk to siesta beach +bikes
Coffee/tea maker, fridge, microwave, oven

7. 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, 84, (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 AED 268
AED 902 total
includes taxes & fees
15 Sep - 16 Sep
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Beach nearby, sun loungers, beach towels

8. 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, 18, (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
On the beach, sun loungers, beach towels

9. Dream Home at Sarasota Gulf Estates Heated pool

Dream Home at Sarasota Gulf Estates Heated pool
Sarasota
9.6 out of 10, 40, (40 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.
The price is AED 661
AED 1,848 total
includes taxes & fees
20 Sep - 21 Sep
Dream Home at Sarasota Gulf Estates Heated pool
TV

10. Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach

Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach
Sarasota
The price is AED 364
AED 692 total
includes taxes & fees
20 Sep - 21 Sep
Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach
Dining

11. 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, 14, (14 reviews)
"Host is really friendly n helpful!! Loved our stay and would definitely stay again "
United States
Kathryn K.
Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly
Interior

12. 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, 10, (10 reviews)
"Great stay, good location, attentive host!"
United States
Ashley E.
The price is AED 516
AED 1,412 total
includes taxes & fees
15 Sep - 16 Sep
Updated Beach House. Walk to Beach, Shop, Waterfront Dining 2 Bed 1 Bath
A heated pool

13. 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, 125, (125 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 1,015 total
includes taxes & fees
27 Sep - 28 Sep
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Interior

14. 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, 26, (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 768
AED 2,298 total
includes taxes & fees
27 Sep - 28 Sep
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
Beach nearby

15. 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, 7, (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 566
AED 2,359 total
includes taxes & fees
20 Sep - 21 Sep
FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West
Beach nearby, sun loungers, beach towels

16. 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, 46, (46 reviews)
"Great spot close to many attractions. Very well appointed with all that you need for a great vacation!"
United States
Suzanne G.
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
Beach

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

Sea Turtle- Full Sized living at Tiny House Siesta
Sarasota
9.4 out of 10, 18, (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 470
AED 823 total
includes taxes & fees
27 Sep - 28 Sep
Sea Turtle- Full Sized living at Tiny House Siesta
Property grounds

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, 21, (21 reviews)
"Host was very helpful. The apt was very comfy"
United States
Barbara B.
The price is AED 374
AED 1,183 total
includes taxes & fees
21 Sep - 22 Sep
Walk to the Beach | Osprey Villa | Siesta Key
Beach towels

19. Poolside Paradise Near Siesta Key Beach

Poolside Paradise Near Siesta Key Beach
Bee Ridge
8.8 out of 10, 12, (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 838
AED 1,750 total
includes taxes & fees
20 Sep - 21 Sep
Poolside Paradise Near Siesta Key Beach
Beach

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, 72, (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
15 Sep - 16 Sep
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"I stay there often whenever im in town. Everything has always been great. Thank you for your intensive customer service."
Chez 1-night trip
Posted 1 hour ago
Kompose Boutique Hotel