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

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

Quick and Easy Walk Downtown - Tons of Amenities

$248

includes taxes & fees

$222 per night

Nov 24 - Nov 25

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

Free WiFi

Air conditioning

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

$272

includes taxes & fees

$244 per night

Dec 1 - Dec 2

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.

Hot Tub

Pet friendly

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

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 Mall at University Town Center and St. Armands Circle.

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 Caspersen Beach.

Pool

Hot Tub

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

$186

includes taxes & fees

$168 per night

Dec 15 - Dec 16

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.

Pool

Free WiFi

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.

Pool

Free WiFi

Siesta key Guest House 5 star on the water Private

$358

includes taxes & fees

$341 per night

Nov 24 - Nov 25

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

Pool

Pet friendly

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

$219

includes taxes & fees

$198 per night

Nov 25 - Nov 26

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

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

$186

includes taxes & fees

$168 per night

Dec 18 - Dec 19

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.

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.

Pool

Hot Tub

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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.