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Compare 27 Guest Houses in Osprey with updated reviews, rates, and availability.

All-New, First Floor, Huge Pool, 70" TV, Tiki Bar!
All-New, First Floor, Huge Pool, 70" TV, Tiki Bar!
9.0 out of 10, Wonderful, (26)
The price is SAR 447
SAR 787 total
includes taxes & fees
19 Apr - 20 Apr

Quick and Easy Walk Downtown - Tons of Amenities
Quick and Easy Walk Downtown - Tons of Amenities
9.8 out of 10, Exceptional, (107)
The price is SAR 548
SAR 859 total
includes taxes & fees
29 Apr - 30 Apr

All-New, Ground-Floor, Huge Pool, Tiki Bar & Grill
All-New, Ground-Floor, Huge Pool, Tiki Bar & Grill
7.6 out of 10, Good, (5)
The price is SAR 447
SAR 787 total
includes taxes & fees
19 Apr - 20 Apr

Close to Siesta Key beach with a hot tub and a large garden
Close to Siesta Key beach with a hot tub and a large garden
9.8 out of 10, Exceptional, (96)
The price is SAR 503
SAR 1,004 total
includes taxes & fees
24 Apr - 25 Apr

Lido Beach Walk! One block to beach!
Lido Beach Walk! One block to beach!
10.0 out of 10, Exceptional, (106)

Downtown Sarasota 2BR Cottage
Downtown Sarasota 2BR Cottage
10.0 out of 10, Exceptional, (2)

Modern, cozy family get-a-way: Bottomless Mimosa
Modern, cozy family get-a-way: Bottomless Mimosa
8.0 out of 10, Very Good, (2)

Private guesthouse near the beach
Private guesthouse near the beach
9.4 out of 10, Exceptional, (20)
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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Other property types in Osprey

Huge Pool, Close to Beaches, Restaurants, Shopping & More!
Huge Pool, Close to Beaches, Restaurants, Shopping & More!
9.6 out of 10, Exceptional, (22)

Tropical Beach Resorts
Tropical Beach Resorts
9.4 out of 10, Exceptional, (4629)
The price is SAR 522
SAR 674 total
includes taxes & fees
21 Apr - 22 Apr

Hibiscus Suites - Gateway to Siesta Key
Hibiscus Suites - Gateway to Siesta Key
8.6 out of 10, Excellent, (2113)
The price is SAR 619
SAR 699 total
includes taxes & fees
4 May - 5 May
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.
Recent reviews of Osprey hotels
Recent reviews of Osprey hotels

Carlisle Inn
5/5 Excellent
"The entire two day stay was excellent. This property was easy to get to. Well appointed, spacious. I stayed in the executive suite that was large and geared towards a business traveler. Washer, dryer, full kitchen, with essentials to take advantage of. Well away from the busier part of the hotel. Staff was friendly, and helpful. I will definitely make this my go to for Sarasota business trips. Could not of been more pleased. "
A verified traveler from West Palm Beach stayed at Carlisle Inn
Posted 19 hours ago