Osprey Guest Houses

Name: NEW!! Gated 2/2 Single-family Guest House! 13 mins to Englewood Beach!
Address: Englewood

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Guest Houses in Osprey

All-New, First Floor, Huge Pool, 70" TV, Tiki Bar!

$187

includes taxes & fees

$168 per night

Jan 12 - Jan 13

With a stay at this guesthouse, you'll be centrally located in Sarasota, within a 15-minute drive of IMG Academy and St. Armands Circle.

Quick and Easy Walk Downtown - Tons of Amenities

$298

includes taxes & fees

$267 per night

Jan 22 - Jan 23

With a stay at this guesthouse, you'll be centrally located in Sarasota, within a 15-minute drive of Lido Beach and St. Armands Circle.

Free WiFi

Air conditioning

The Cottages at Siesta Key

1105 Point of Rocks Rd, Siesta Key, FL

With a stay at The Cottages at Siesta Key in Siesta Key, you'll be near the beach, just a 4-minute walk from Crescent Beach and a 3-minute drive from Siesta Key Beach.

Pool

Pet friendly

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

$268

includes taxes & fees

$240 per night

Jan 11 - Jan 12

With a stay at this guesthouse, you'll be centrally located in Sarasota, within a 5-minute drive of Siesta Key Beach and Sarasota Memorial Health Care System.

Adorable 1920s Cottage in a Tropical Wooded Setting!

With a stay at this guesthouse, you'll be centrally located in Sarasota, within a 15-minute drive of St. Armands Circle and Northeast Plaza Shopping Center.

Free WiFi

Air conditioning

Amazing Location West of the Trail

With a stay at this guesthouse, you'll be centrally located in Sarasota, within a 10-minute drive of Siesta Key Beach and St. Armands Circle.

Pool

Free WiFi

Modern, cozy family get-a-way: Bottomless Mimosa

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

Pool

Hot Tub

All-New, Bunk Bed, Huge Pool, 70" TV, Tiki Bar & Grill!

With a stay at this guesthouse, you'll be centrally located in Sarasota, within a 15-minute drive of IMG Academy and St. Armands Circle.

Siesta key Guest House 5 star on the water Private

$469

includes taxes & fees

$441 per night

Feb 1 - Feb 2

With a stay at this guesthouse in Sarasota (South Sarasota), you'll be within a 15-minute drive of Siesta Key Beach and St. Armands Circle.

All-New, Private, 70" TV, Heated Pool, Tiki Bar & Grill

$187

includes taxes & fees

$168 per night

Jan 7 - Jan 8

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.

All-New, Ground-Floor, Huge Pool, Tiki Bar & Grill

$187

includes taxes & fees

$168 per night

Jan 7 - Jan 8

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.

Pool

Free WiFi

NEW!! Gated 2/2 Single-family Guest House! 13 mins to Englewood Beach!

Located in Englewood, this guesthouse is in a rural location, a 5-minute drive from Myakka State Forest and 7 minutes from Lemon Bay Playhouse.

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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.