A marina with docked boats, a wooden bridge, and a building with a red roof.

Search Country Houses in Osprey

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Osprey

A pathway flanked by palm trees and a building with a covered patio area.

1. Casey Key Resorts - Mainland

Casey Key Resorts - Mainland
4.0 star property
Osprey
8.6 out of 10, Excellent, (1,262 reviews)
"Clean room, nice staff and great pool area."
United States
Vito
$92 nightly
The price is $104
Dec 8 - Dec 9
Total with taxes and fees
Casey Key Resorts - Mainland
A modern kitchen with a white countertop, a black kettle, a sink with a black faucet, and a hanging light fixture.

2. 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.
$328 nightly
The price is $368
Nov 10 - Nov 11
Total with taxes and fees
Charming Osprey Home
A modern kitchen with a central island, bar stools, and a clock on the wall.

3. Sunny Coastal Escape

Sunny Coastal Escape
Bay Acres
10.0 out of 10, Exceptional, (6 reviews)
"We were centerally located and had an easy drive to the beach and park. "
United States
Jennifer A.
$366 nightly
The price is $410
Nov 10 - Nov 11
Total with taxes and fees
Sunny Coastal Escape
A tented accommodation with a bed, pillows, a desk, and chairs.

4. Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
10.0 out of 10, Exceptional, (1 review)
$329 nightly
The price is $357
Nov 16 - Nov 17
Total with taxes and fees
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
A tented accommodation with a central bed, bedside tables, a hanging light fixture, and a patterned floor.

5. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
$329 nightly
The price is $357
Nov 10 - Nov 11
Total with taxes and fees
Charming Secluded Tented Cabin in Sarasota, Florida
A tented accommodation with a bed, pillows, a desk, and chairs.

6. Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
$327 nightly
The price is $355
Nov 10 - Nov 11
Total with taxes and fees
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
A tent with two chairs and a checkered mat in a forest.

7. Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
$329 nightly
The price is $357
Nov 10 - Nov 11
Total with taxes and fees
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.

8. Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway
3.0 star property
Sarasota
8.2 out of 10, Very good, (2,524 reviews)
"Will stay there again."
United States
kathryn
$97 nightly
The price is $109
Nov 29 - Nov 30
Total with taxes and fees
Spark by Hilton Sarasota Siesta Key Gateway
A pool area with a waterfall feature, lounge chairs, and palm trees.

9. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,054 reviews)
"Great resort and location!"
United States
Christine
$179 nightly
The price is $203
Nov 29 - Nov 30
Total with taxes and fees
Tropical Beach Resorts
A reception area with two reception desks, a blue geometric wall design, and a wooden panel accent.

10. Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG
2.5 star property
Nokomis
9.4 out of 10, Exceptional, (630 reviews)
"Good breakfast and great location."
United States
Linda
$101 nightly
The price is $114
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Nokomis Sarasota South by IHG
A lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.

11. Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
3.0 star property
Sarasota
9.0 out of 10, Wonderful, (1,802 reviews)
"Nice location nice rooms friendly night staff"
United States
Jymieka
$95 nightly
The price is $108
Nov 29 - Nov 30
Total with taxes and fees
Comfort Suites Sarasota - Siesta Key
A hotel with a covered outdoor seating area, palm trees, and a sign reading "HOME 2".

12. Home2 Suites by Hilton Nokomis Sarasota Casey Key

Home2 Suites by Hilton Nokomis Sarasota Casey Key
3.0 star property
Nokomis
9.2 out of 10, Wonderful, (963 reviews)
"Clean room , clean towels, good breakfast, and very nice friendly staff"
Canada
Sonila
$114 nightly
The price is $129
Nov 15 - Nov 16
Total with taxes and fees
Home2 Suites by Hilton Nokomis Sarasota Casey Key
A hotel with a pool, palm trees, and a sign reading "Twin Palms."

13. Twin Palms at Siesta

Twin Palms at Siesta
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (609 reviews)
"Awesome place! It’s super convenient and within easy walking distance of the beach and restaurants."
United States
Leonardo
$186 nightly
The price is $210
Nov 15 - Nov 16
Total with taxes and fees
Twin Palms at Siesta
A living room with a TV, white cabinets, a sofa, and a balcony with a view.

14. Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key
2.5 star property
Casey Key
9.6 out of 10, Exceptional, (330 reviews)
"Very clean and close to both the bay and the beach. Had everything we needed for our stay and more. It was nice to have the bicycles on the property for use as well as beach chairs wagon and umbrella."
United States
Amy
$143 nightly
The price is $162
Nov 30 - Dec 1
Total with taxes and fees
Escape Coastal Resort on Casey Key
A hotel with a palm tree entrance, a neon sign, and a tiled roof.

15. Inn at the Beach

Inn at the Beach
3.0 star property
Venice Island
9.8 out of 10, Exceptional, (1,107 reviews)
"Beautiful, clean property in a great location!"
United States
Catherine
$175 nightly
The price is $198
Nov 22 - Nov 23
Total with taxes and fees
Inn at the Beach
A spacious lobby with a central seating area, a kitchen in the background, and a large chandelier.

16. Hampton Inn & Suites Venice Bayside South Sarasota

Hampton Inn & Suites Venice Bayside South Sarasota
2.5 star property
Gateway
9.0 out of 10, Wonderful, (1,003 reviews)
"Very clean very good breakfast wonderful stuff"
United States
Dumitru
$109 nightly
The price is $123
Nov 15 - Nov 16
Total with taxes and fees
Hampton Inn & Suites Venice Bayside South Sarasota
A modern house with a patio, outdoor seating, and a view of the ocean.

17. Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront
3.0 star property
Casey Key
8.8 out of 10, Excellent, (1,006 reviews)
"Fantastic love the place great location. Great rooms would stay again."
United States
Phil
$106 nightly
The price is $120
Dec 9 - Dec 10
Total with taxes and fees
Casey Key Resorts - Beachfront
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a multi-story building.

18. Cottages at Siesta Key Inn

Cottages at Siesta Key Inn
3.0 star property
South Village
8.8 out of 10, Excellent, (294 reviews)
"Basic no frills place to stay."
United States
Richard
$104 nightly
The price is $117
Dec 10 - Dec 11
Total with taxes and fees
Cottages at Siesta Key Inn
An outdoor patio with a grill, white chairs, and a red umbrella.

19. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,480 reviews)
"This place was perfect!"
United States
Kat
$152 nightly
The price is $172
Nov 24 - Nov 25
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A Holiday Inn Express hotel with a covered entrance, palm trees, and a well-lit facade.

20. Holiday Inn Express Sarasota East - I-75 by IHG

Holiday Inn Express Sarasota East - I-75 by IHG
2.5 star property
Sarasota
8.4 out of 10, Very good, (1,006 reviews)
"It was great, the breakfast was good, staff was nice and the property had all the facilities."
United States
Yash
$90 nightly
The price is $102
Nov 29 - Nov 30
Total with taxes and fees
Holiday Inn Express Sarasota East - I-75 by IHG
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"Staff was great. At the desk Ginny—at the bar Lynn and sorry to say I didn’t get the name of young lady who came to fix our TV Friday night very quickly took care of it for us. Recommendations made from staff on where to eat were excellent. We were there for a sad occasion (mom’s funeral mass)but it was great to have our family together in one place."
Margaret A. 3-night trip
Posted 2 hours ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Osprey Country Houses information

Number of reviews
9,743
Accommodation
0 Country Houses
Lowest Price
$102
Highest Price
$410