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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, Very good, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is AED 334
AED 1,117 total
includes taxes & fees
22 Sep - 23 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, Exceptional, (81 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is AED 398
AED 1,219 total
includes taxes & fees
30 Sep - 1 Oct
Siesta Key Island Rentals
Outdoor pool, a heated pool

3. 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 386
AED 901 total
includes taxes & fees
19 Sep - 20 Sep
The Dolphin
Interior

4. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (93 reviews)
"Loved the house. It had everything you could possibly need"
United States
Erin G.
The price is AED 1,252
AED 2,638 total
includes taxes & fees
12 Oct - 13 Oct
Oceanfront home
Beach

5. 2 miles to #1 Beach Siesta Key

2 miles to #1 Beach Siesta Key
Sarasota
9.8 out of 10, Exceptional, (85 reviews)
"Great stay, as always! Clean, comfortable, and everything you need."
United States
Kelley B.
The price is AED 477
AED 1,305 total
includes taxes & fees
18 Oct - 19 Oct
2 miles to #1 Beach Siesta Key
Interior

6. 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 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!
On the beach, sun loungers, beach towels

7. Dream Home at Sarasota Gulf Estates Heated pool

Dream Home at Sarasota Gulf Estates Heated pool
Sarasota
9.6 out of 10, Exceptional, (41 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
Beach

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 320
AED 642 total
includes taxes & fees
20 Sep - 21 Sep
The Mermaid at Tiny House Siesta
Outdoor dining

9. 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)
"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "
United States
Sandra C.
The price is AED 401
AED 1,339 total
includes taxes & fees
19 Sep - 20 Sep
Dolphin Villa - Pool - Steps to Siesta Key Village
Coffee/tea maker, fridge, microwave, oven

10. [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)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
The price is AED 375
AED 1,166 total
includes taxes & fees
27 Sep - 28 Sep
[lounge like locals] walk to siesta beach +bikes
Beach

11. 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
Coffee/tea maker, fridge, microwave, oven

12. Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota

Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota
Sarasota
9.8 out of 10, Exceptional, (8 reviews)
"This was a great stay for us. It was extremely clean and just as described."
United States
Kenzie Q.
Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota
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, 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 1,015 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
Beach nearby, sun loungers, beach towels

14. 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
Property grounds

15. 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 380
AED 1,436 total
includes taxes & fees
20 Sep - 21 Sep
Island Villa | Cozy Beach Retreat | Walk to Village
Microwave, oven, stovetop

16. Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.
Kensington Park
9.2 out of 10, Wonderful, (35 reviews)
"My husband and I really enjoyed our stay at this home. It was clean, nicely decorated, and had everything we needed. The host was very responsive and friendly. The neighborhood was quiet and nice. The AC works well."
United States
Julie B.
The price is AED 380
AED 857 total
includes taxes & fees
19 Sep - 20 Sep
Charming 2-bedroom house in lovely Sarasota with yard.
Beach nearby, sun loungers, beach towels

17. 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.
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
Smart TV, DVD player

18. 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 1,705 total
includes taxes & fees
22 Sep - 23 Sep
Siesta beach....one and only
Beach towels

19. 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 838
AED 1,761 total
includes taxes & fees
19 Sep - 20 Sep
Poolside Paradise Near Siesta Key Beach
Outdoor dining

20. Luxury Family Home Near Downtown & Siesta Key Beach

Luxury Family Home Near Downtown & Siesta Key Beach
Alta Vista
9.8 out of 10, Exceptional, (81 reviews)
"Excellent property at a great value. Very clean and centrally located. "
United States
Joseph C.
Luxury Family Home Near Downtown & Siesta Key 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.
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Top Osprey Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

8/10 Good
"Boutique style family friendly place, very pleasant--with 2 pools & a very short walk to the private beach. 👍 The staff are friendly and professional. The property & rooms are in excellent condition and very clean!"
Maryann 3-night trip
Posted 2 hours ago
Tropical Beach Resorts