Winter Garden Cottages

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Cottages in Winter Garden

Encore Swanky

411 Lasso Drive Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.

Pool

Kitchen

Tiny Hidden Cottage

Longwood FL

$131 nightly

$144 total

Dec 8 - Dec 9

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.

Kitchen

Free WiFi

Enchanted Cottage with Pool and Mini-Golf Near Disney

Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be a 3-minute drive from Old Town and 9 minutes from Orlando Vineland Premium Outlets.

Pool

Hot Tub

Historic Tremain Cottages

619 N Tremain St Mount Dora FL

$218 nightly

$242 total

Dec 30 - Dec 31

Total with taxes and fees

With a stay at Historic Tremain Cottages in Mount Dora, you'll be just steps from Mount Dora Community Building and Donnelly Park.

Kitchen

Pet friendly

1 bedroom, private laundry in resort with a pool near Disney!! Kissimmee

Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be a 3-minute drive from Old Town and 9 minutes from Walt Disney World® Resort.

Pool

Hot Tub

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

Orlando FL

$337 nightly

$374 total

Dec 8 - Dec 9

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

Cozy Mount Dora Cottage /Walk Downtown/ Pet Friendly / Fenced Yard

Mount Dora FL

A stay at this cottage places you in the heart of Mount Dora, within a 5-minute walk of Donnelly Park and Mount Dora Community Building.

Kitchen

Washer

High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

Mt Dora FL

Located in Mount Dora, this cottage is within a 5-minute drive of Lake Dora and Mount Dora Center for the Arts.

Kitchen

Free WiFi

Guesthouse Retreat – Private Pool & King Suite

Lake Mary FL

$243 nightly

$268 total

Dec 11 - Dec 12

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

Solterra Swanky

5180 Oakbourne Avenue Davenport FL

With a stay at this cottage in Davenport (Solterra Resort), you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club.

Pool

Kitchen

Watersong Swanky

1209 Butterfly Orchid Road Davenport FL

With a stay at this cottage in Davenport, you'll be within a 15-minute drive of Providence Golf Club and Lewis W Mathews Memorial Sports Complex.

Pool

Kitchen

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™.

Pool

Kitchen

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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.