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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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 HK$1,255
HK$3,061 total
includes taxes & fees
8 Aug - 9 Aug
Charming Osprey Home
Living area

2. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is HK$953
HK$2,655 total
includes taxes & fees
10 Aug - 11 Aug
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, (27 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 HK$925
HK$2,873 total
includes taxes & fees
10 Aug - 11 Aug
Beachside Bliss: Family House-Siesta Key-3BR/2BA
Private kitchen

4. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (75 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is HK$1,309
HK$3,148 total
includes taxes & fees
10 Aug - 11 Aug
Siesta Key Island Rentals
Outdoor pool, a heated pool

5. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (14 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is HK$1,373
HK$2,615 total
includes taxes & fees
20 Aug - 21 Aug
The Dolphin
Interior

6. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (92 reviews)
"Loved the house. It had everything you could possibly need"
United States
Erin G.
The price is HK$3,130
HK$6,281 total
includes taxes & fees
23 Aug - 24 Aug
Oceanfront home
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
9.8 out of 10, Exceptional, (36 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 HK$1,412
HK$3,954 total
includes taxes & fees
6 Sept - 7 Sept
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 HK$949
HK$1,712 total
includes taxes & fees
20 Aug - 21 Aug
The Mermaid at Tiny House Siesta
Property grounds

9. The Ashton Hideaway

The Ashton Hideaway
2.0 star property
Sarasota
The Ashton Hideaway
Beach

10. Cozy Beach House Just Minutes From Siesta Key

Cozy Beach House Just Minutes From Siesta Key
Sarasota
9.0 out of 10, Wonderful, (17 reviews)
"Loved it"
United States
MIRIAM
The price is HK$1,050
HK$2,339 total
includes taxes & fees
10 Aug - 11 Aug
Cozy Beach House Just Minutes From Siesta Key
Coffee/tea maker, fridge, microwave, oven

11. 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, (82 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 HK$628
HK$2,053 total
includes taxes & fees
10 Aug - 11 Aug
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
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, (23 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 HK$1,859
HK$5,280 total
includes taxes & fees
19 Aug - 20 Aug
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
Beach nearby

13. 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 HK$1,753
HK$3,486 total
includes taxes & fees
1 Sept - 2 Sept
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
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, (17 reviews)
"Great place close to beach and great food restaurants "
United States
Adan M.
The price is HK$1,188
HK$2,856 total
includes taxes & fees
8 Aug - 9 Aug
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
2 bedrooms, iron/ironing board, WiFi, bed sheets

15. Charming 2-bedroom house in cool Sarasota with AC

Charming 2-bedroom house in cool Sarasota with AC
South Sarasota
7.8 out of 10, Good, (13 reviews)
"Location is in a nice area."
United States
Leon A.
The price is HK$635
HK$2,061 total
includes taxes & fees
10 Aug - 11 Aug
Charming 2-bedroom house in cool Sarasota with AC
A heated pool

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, (125 reviews)
"very convenient, it was right in front of the event center that my daughter was dancing."
United States
erica
The price is HK$1,216
HK$2,222 total
includes taxes & fees
9 Aug - 10 Aug
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Dining

17. Sunny 3BR Oasis • Water View • Beach Gear • Fully Fenced Yard • Near Siesta Key

Sunny 3BR Oasis • Water View • Beach Gear • Fully Fenced Yard • Near Siesta Key
Sarasota Springs
10.0 out of 10, Exceptional, (11 reviews)
"Host is really friendly n helpful!! Loved our stay and would definitely stay again "
United States
Kathryn K.
The price is HK$812
HK$2,819 total
includes taxes & fees
8 Aug - 9 Aug
Sunny 3BR Oasis • Water View • Beach Gear • Fully Fenced Yard • Near Siesta Key
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)
"Great house and great pool. AC struggled and there’s a bit of an ant problem, but overall great house. "
United States
Jake L.
The price is HK$1,352
HK$3,179 total
includes taxes & fees
9 Aug - 10 Aug
Poolside Paradise Near Siesta Key Beach
Exterior

19. Luxury Siesta Key townhome close to village,beaches, city and airport

Luxury Siesta Key townhome close to village,beaches, city and airport
Siesta Key
9.0 out of 10, Wonderful, (31 reviews)
"Perfect spot to stay near Siesta Key village, would definitely stay here again! "
United States
Dale R.
The price is HK$793
HK$2,001 total
includes taxes & fees
12 Aug - 13 Aug
Luxury Siesta Key townhome close to village,beaches, city and airport
Outdoor dining

20. 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 HK$1,037
HK$3,128 total
includes taxes & fees
17 Aug - 18 Aug
Dolphin Villa - Pool - Steps to Siesta Key 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
"Staff"
Timmy 2-night trip
Posted 8 hours ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Osprey Vacation Homes information

Number of reviews
517
Accommodation
4076 Vacation Homes
Lowest Price
HK$1,712
Highest Price
HK$6,281

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