Winter Park Cottages

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Cottages in Winter Park

Tiny Hidden Cottage

Longwood FL

$130 nightly

$143 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this cottage in Longwood, you'll be within a 5-minute drive of Altamonte Mall and Cranes Roost Park.

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

Orlando FL

$345 nightly

$382 total

Dec 14 - Dec 15

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.

Guesthouse Retreat – Private Pool & King Suite

Lake Mary FL

$256 nightly

$283 total

Jan 6 - Jan 7, 2026

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 Spring Hammock Preserve.

Stunning Lakeview Townhome w/ Private Pool!

4893 Romeo Circle Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Old Town and Disney Springs™.

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 9 minutes from Disney Springs™.

Incredible Private Lakefront Cottage Retreat

Altamonte Springs FL

$295 nightly

$326 total

Dec 15 - Dec 16

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.

Orlando Lakefront Tiny House Community

3405 N Orange Blossom Trail Orlando FL

$145 nightly

$163 total

Dec 14 - Dec 15

Total with taxes and fees

When you stay at Orlando Lakefront Tiny House Community in Orlando, you'll be on the waterfront, within a 10-minute drive of Kia Center and Camping World Stadium.

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.

Caribbean Dreamin Vibrant Margaritaville Resort

Kissimmee FL

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

Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,

Altamonte Springs FL

$287 nightly

$317 total

Dec 22 - Dec 23

Total with taxes and fees

Located in Altamonte Springs, this cottage is within a 5-minute drive of AdventHealth Altamonte Springs and Altamonte Mall.

Relaxing 2-bedroom cottage in beautiful Sanford

Sanford FL

With a stay at this cottage in Sanford, you'll be within a 10-minute drive of Central Florida Zoo & Botanical Gardens and HCA Florida Lake Monroe Hospital.

2BR COTTAGE IN SANFORD HISTORIC DISTRICT

Sanford FL

With a stay at this cottage, you'll be centrally located in Sanford, within a 10-minute drive of Central Florida Zoo & Botanical Gardens and Wayne Dench Performing Arts Center.

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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.