Osprey Guest Houses

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Guest Houses in Osprey

Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball

Sarasota FL

$163 nightly

$182 total

Jun 16 - Jun 17

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 7 minutes from St. Armands Circle.

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

Sarasota FL

$235 nightly

$262 total

Jul 15 - Jul 16

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 8 minutes from Turtle Beach.

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.

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 4-minute walk from Lido Beach and 11 minutes by foot from St. Armands Circle.

Cozy studio "glamping" shack 2 miles from Englewood Beach!

Englewood FL

With a stay at this guesthouse in Englewood (Englewood Central), you'll be within a 10-minute drive of Englewood Beach and Manasota Beach.

Pet friendly

Free WiFi

Siesta key Guest House 5 star on the water Private

Sarasota FL

$394 nightly

$416 total

Jul 15 - Jul 16

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.

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.

Travelers Nook close to Venice Beach!

Venice FL

With a stay at this guesthouse in Venice (Venice Gardens), you'll be within a 15-minute drive of Venice Beach and Manasota Beach.

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 Nathan Benderson Park and Sarasota Memorial Hospital.

ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

Sarasota FL

$202 nightly

$236 total

Jun 19 - Jun 20

Total with taxes and fees

With a stay at this guesthouse in Sarasota (Whitfield Estates), you'll be within a 10-minute drive of IMG Academy and LECOM Park.

Magical Guesthouse 1 mi from SRQ airport

Sarasota FL

$245 nightly

$245 total

Jun 29 - Jun 30

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 St. Armands Circle.

Bayfront Beauty

4024 Casey Key Rd Nokomis FL

With a stay at Bayfront Beauty in Nokomis, you'll be within a 15-minute walk of Turtle Beach and Nokomis Beach.

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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.