Winter Park Cottages

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Cottages in Winter Park

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

Orlando FL

$294 nightly

$326 total

Sep 13 - Sep 14

Total with taxes and fees

With a stay at this cottage in Orlando (College Park), you'll be within a 5-minute drive of Kia Center and Camping World Stadium.

Kitchen

Washer

Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Lake Mary FL

$211 nightly

$233 total

Aug 26 - Aug 27

Total with taxes and fees

With a stay at this cottage in Lake Mary, you'll be within a 5-minute drive of Lake Mary Farmer's Market and Boombah-Soldiers Creek Park.

Pool

Kitchen

Early Check In Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits

Lake Mary FL

$222 nightly

$245 total

Sep 3 - Sep 4

Total with taxes and fees

With a stay at this cottage in Lake Mary, you'll be within a 5-minute drive of Lake Mary Farmer's Market and Boombah-Soldiers Creek Park.

Downtown Cottage

Orlando FL

$150 nightly

$167 total

Aug 26 - Aug 27

Total with taxes and fees

With a stay at this cottage, you'll be centrally located in Orlando, a 5-minute drive from Kia Center and 14 minutes from Universal CityWalk.

2BR COTTAGE IN SANFORD HISTORIC DISTRICT

Sanford FL

A stay at this cottage places you in the heart of Sanford, within a 10-minute walk of The Princess Theater and Wayne Dench Performing Arts Center.

Kitchen

Washer

AUGUST SUN SPECIAL - Floating Cottage on St Johns River

Sanford FL

With a stay at this cottage in Sanford, you'll be on the waterfront, within a 15-minute drive of Wekiwa Springs State Park and Lake Monroe.

Family-Friendly Cottage Near Disney with Pool, Playground & Resort Amenities

Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Florida Mall and Old Town.

Lovely Spacious Guesthouse in Mills 50 District, Orlando

Orlando FL

With a stay at this cottage in Orlando (Colonialtown North), you'll be a 5-minute drive from Kia Center and 7 minutes from Camping World Stadium.

Kitchen

Washer

Incredible Private Lakefront Cottage Retreat

Altamonte Springs FL

$327 nightly

$361 total

Sep 1 - Sep 2

Total with taxes and fees

With a stay at this cottage in Altamonte Springs, you'll be on the waterfront, within a 15-minute drive of Kia Center and AdventHealth Altamonte Springs.

Chic Luxury Haven - Unforgettable Retreat

Kings Castle Circle 4821 Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets.

5003 Windermere Avenue

5003 Windermere Avenue, Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be a 4-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets.

4177 Paragraph Drive

4177 Paragraph Drive Kissimmee FL

Located in Kissimmee, this cottage is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.

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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.