Osprey Guest Houses

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Guest Houses in Osprey

Close to Siesta Key beach with a hot tub and a large garden

Sarasota FL

$220 nightly

$246 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this guesthouse, you'll be centrally located in Sarasota, a 4-minute drive from Siesta Key Beach and 7 minutes from Sarasota Memorial Hospital.

Hot Tub

Pet friendly

Adorable 1920s Cottage in a Tropical Wooded Setting!

Sarasota FL

With a stay at this guesthouse, you'll be centrally located in Sarasota, within a 10-minute drive of Sarasota Memorial Hospital and Mall at University Town Center.

Free WiFi

Air conditioning

Quick and Easy Walk Downtown - Tons of Amenities

Sarasota FL

$196 nightly

$219 total

Dec 7 - Dec 8

Total with taxes and fees

Free Cancellation

With a stay at this guesthouse, you'll be centrally located in Sarasota, a 2-minute drive from Sarasota Memorial Hospital and 11 minutes from Lido Beach.

Free WiFi

Air conditioning

Lido Beach Walk! One block to beach!

Sarasota FL

With a stay at this guesthouse in Sarasota, you'll be near the beach, a 3-minute walk from Lido Beach and 12 minutes by foot from St. Armands Circle.

Pool

Air conditioning

Amazing Location West of the Trail

Sarasota FL

With a stay at this guesthouse, you'll be centrally located in Sarasota, a 2-minute drive from Sarasota Memorial Hospital and 7 minutes from Siesta Key Beach.

Pool

Free WiFi

Private guesthouse near the beach

Sarasota FL

Located in Sarasota (Vamo), this guesthouse is within a 10-minute drive of Siesta Key Beach and Nokomis Beach.

Air conditioning

Gym

Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach

Sarasota FL

With a stay at this guesthouse in Sarasota, you'll be near the beach, a 3-minute walk from Lido Beach and 11 minutes by foot from St. Armands Circle.

Free WiFi

Air conditioning

Travelers Nook close to Venice Beach!

Venice FL

With a stay at this guesthouse in Venice (Venice Gardens), you'll be within a 10-minute drive of Venice Beach and Jacaranda West Country Club.

Pool

Pet friendly

Downtown Sarasota 2BR Cottage

318 S Shade Ave Sarasota FL

With a stay at Downtown Sarasota 2BR Cottage in Sarasota (Downtown Sarasota), you'll be a 3-minute drive from Sarasota Memorial Hospital and 8 minutes from St. Armands Circle.

Pet friendly

Free WiFi

Magical Guesthouse 1 mi from SRQ airport

Sarasota FL

$246 nightly

$246 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this guesthouse in Sarasota (Whitfield Estates), you'll be within a 15-minute drive of IMG Academy and Sarasota Memorial Hospital.

Laundry

Siesta key Guest House 5 star on the water Private

Sarasota FL

$435 nightly

$463 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at this guesthouse in Sarasota (South Sarasota), you'll be a 4-minute drive from Sarasota Memorial Hospital and 7 minutes from Siesta Key Beach.

Pool

Pet friendly

Luxury Pool Retreat near Siesta Key

6007 Beneva Rd Sarasota FL

With a stay at Luxury Pool Retreat near Siesta Key in Sarasota, you'll be within a 10-minute drive of Siesta Key Beach and Sarasota Memorial Hospital.

Pool

Pet friendly

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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.