Winter Park Cottages

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Cottages in Winter Park

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

Orlando FL

$296 nightly

$329 total

Nov 4 - Nov 5

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

Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Lake Mary FL

$257 nightly

$284 total

Nov 3 - Nov 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 Spring Hammock Preserve.

Pool

Kitchen

Tiny Hidden Cottage

Longwood FL

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

Kitchen

Free WiFi

PRIVATE LAKEFRONT + DOCK Bring your boat, Hot Tub, Kayaks, Paddleboards

Montverde FL

Located in Montverde, this cottage is by the sea, within a 10-minute drive of Ferndale Preserve and Johns Lake.

Hot Tub

Kitchen

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

FLOATING COTTAGE - Unique home afloat on the St. John's River

Sanford FL

Located in Sanford, this cottage is on the waterfront, within a 5-minute drive of Lake Monroe and Central Florida Zoo & Botanical Gardens.

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

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Lake Mary FL

$223 nightly

$246 total

Nov 2 - Nov 3

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.

Kitchen

Washer

Garden Cottage-2bdrms/1.5 Bath, Swim&Spa, Ctrl Orlando Disney Universal SeaWorld

Altamonte Springs FL

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

Pool

Hot Tub

Relaxing 2-bedroom cottage in beautiful Sanford

Sanford FL

With a stay at this cottage in Sanford, you'll be within a 15-minute walk of The Princess Theater and Lake Monroe.

The Cozy Euphoric cottage nestled in nature with relaxing River front views.

Osteen FL

With a stay at this cottage in Osteen, you'll be on a river, and 5.2 mi (8.4 km) from Lake Monroe Conservation Area and 5.8 mi (9.3 km) from Pell's Citrus & Nursery.

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.

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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.