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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Osprey holiday homes

Beach towels

1. Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
The price is £333
includes taxes & fees
11 Sept - 12 Sept
Charming Osprey Home
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

2. 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 £225
includes taxes & fees
1 Sept - 2 Sept
Siesta Heron Suites & Villas
Dining

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 £246
includes taxes & fees
31 Aug - 1 Sept
Beachside Bliss: Family House-Siesta Key-3BR/2BA
Beach nearby, beach umbrellas, beach towels

4. Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (268 reviews)
"It was amazing and way beyond what I thought. Easy walk to beach(0.4 mikes) and shops. Private location with small pool. Just what you need."
United States
Christina
The price is £86
includes taxes & fees
30 Aug - 31 Aug
Tropical Villas of Venice Beach
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

5. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is £237
includes taxes & fees
31 Aug - 1 Sept
Siesta Key Island Rentals
Beach nearby

6. 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)
"Very nice, clean and quiet place."
United States
Monika Z.
The price is £312
includes taxes & fees
31 Aug - 1 Sept
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Outdoor pool, a heated pool

7. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (17 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is £181
includes taxes & fees
30 Aug - 31 Aug
The Dolphin
Coffee/tea maker, fridge, microwave, oven

8. [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 £218
includes taxes & fees
7 Sept - 8 Sept
[lounge like locals] walk to siesta beach +bikes
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
9.8 out of 10, Exceptional, (38 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 £360
includes taxes & fees
31 Aug - 1 Sept
Dream Home at Sarasota Gulf Estates Heated pool
Outdoor pool, a heated pool

10. Oceanfront home w/sunset views of Sarasota Bay

Oceanfront home w/sunset views of Sarasota Bay
Vamo
9.8 out of 10, Exceptional, (132 reviews)
"Excellent place to stay"
United States
Bob E.
Oceanfront home w/sunset views of Sarasota Bay
Beach

11. 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 £152
includes taxes & fees
11 Sept - 12 Sept
The Mermaid at Tiny House Siesta
Interior

12. 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, (24 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 £470
includes taxes & fees
4 Sept - 5 Sept
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
Dining

13. 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, (13 reviews)
"Host is really friendly n helpful!! Loved our stay and would definitely stay again "
United States
Kathryn K.
The price is £239
includes taxes & fees
30 Aug - 31 Aug
Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly
A heated pool

14. 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, (125 reviews)
"very convenient, it was right in front of the event center that my daughter was dancing."
United States
erica
The price is £208
includes taxes & fees
1 Sept - 2 Sept
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Coffee/tea maker, fridge, microwave, oven

15. 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, Exceptional, (84 reviews)
The price is £197
includes taxes & fees
8 Sept - 9 Sept
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Beach nearby, sun-loungers, beach towels

16. 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 £281
includes taxes & fees
30 Aug - 31 Aug
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
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, 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 £170
includes taxes & fees
4 Sept - 5 Sept
Sea Turtle- Full Sized living at Tiny House Siesta
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 £320
includes taxes & fees
30 Aug - 31 Aug
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.
The price is £285
includes taxes & fees
31 Aug - 1 Sept
Island Villa | Cozy Beach Retreat | Walk to Village
Beach nearby, sun-loungers, beach towels

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 £327
includes taxes & fees
30 Aug - 31 Aug
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

Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Excellent location, short walk yo the beach. The pool and hot tub were great. Staff was friendly and helpful. Would definitely stay again!"
Jill 2-night trip
Posted less than an hour ago
Siesta Key Beach Resort and Suites

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews
884
Accommodation
3972 Holiday Homes
Lowest Price
£86
Highest Price
£470