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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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 335
AED 1,117 total
includes taxes & fees
30 Sep - 1 Oct
Siesta Heron Suites & Villas
Dining

2. 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 357
AED 1,182 total
includes taxes & fees
5 Oct - 6 Oct
Beachside Bliss: Family House-Siesta Key-3BR/2BA
Interior

3. 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 966
AED 2,164 total
includes taxes & fees
3 Oct - 4 Oct
Oceanfront home
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

4. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.4 out of 10, Exceptional, (81 reviews)
"The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!"
United States
Meghan
The price is AED 370
AED 1,186 total
includes taxes & fees
30 Sep - 1 Oct
Siesta Key Island Rentals
Outdoor pool, a heated pool

5. 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 883 total
includes taxes & fees
29 Sep - 30 Sep
The Dolphin
Interior

6. 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
29 Sep - 30 Sep
Cozy 1-bedroom private room in Sarasota.
Beach

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
29 Sep - 30 Sep
The Mermaid at Tiny House Siesta
Outdoor dining

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 477
AED 1,236 total
includes taxes & fees
18 Oct - 19 Oct
2 miles to #1 Beach Siesta Key
Interior

9. 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, (44 reviews)
"Great location and the house had everything needed for a great stay. Thanks Tim!"
United States
George B.
The price is AED 808
AED 1,941 total
includes taxes & fees
23 Oct - 24 Oct
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Interior

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 782
AED 2,208 total
includes taxes & fees
29 Sep - 30 Sep
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
Coffee/tea maker, fridge, microwave, oven

11. [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 291
AED 1,022 total
includes taxes & fees
29 Sep - 30 Sep
[lounge like locals] walk to siesta beach +bikes
Beach

12. 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 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 1,007 total
includes taxes & fees
29 Sep - 30 Sep
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Coffee/tea maker, fridge, microwave, oven

14. 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.
The price is AED 544
AED 1,310 total
includes taxes & fees
29 Sep - 30 Sep
Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota
Smart TV, DVD player

15. 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 1,620 total
includes taxes & fees
29 Sep - 30 Sep
Siesta beach....one and only
Dining

16. 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, Exceptional, (14 reviews)
"Host is really friendly n helpful!! Loved our stay and would definitely stay again "
United States
Kathryn K.
The price is AED 314
AED 1,175 total
includes taxes & fees
29 Sep - 30 Sep
Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly
Outdoor dining

17. 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 401
AED 1,266 total
includes taxes & fees
29 Sep - 30 Sep
Dolphin Villa - Pool - Steps to Siesta Key Village
Beach towels

18. 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 717
AED 1,507 total
includes taxes & fees
29 Sep - 30 Sep
Poolside Paradise Near Siesta Key Beach
Property grounds

19. 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.
Island Villa | Cozy Beach Retreat | Walk to Village
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, Exceptional, (72 reviews)
"It was very clean and close to the beach. Perfect location."
United States
Cortney
The price is AED 789
AED 2,061 total
includes taxes & fees
29 Sep - 30 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

The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Great stay. Highly recommend."
Melanie 1-night trip
Posted 4 hours ago
The Westin Sarasota