Windermere Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Cottages in Windermere

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

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

Downtown Cottage

Orlando FL

$150 nightly

$167 total

Aug 27 - Aug 28

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.

Kitchen

Washer

Up to Scale With Margaritas

8021 Sandy Toes Way, Kissimmee, Fl Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort.

Our Retro Mod Pod-Disney & Old Town Minutes Away! Family Friendly Amenity Rich

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

Enchanted Cottage with Pool and Mini-Golf Near Disney

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.

Pool

Hot Tub

Gorgeous Cottage w/Private Pool + Balcony, Near Disney!

Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort.

Pool

Kitchen

Luxury 6BR Home w/ Theater + Pool Near Disney

Bismarck Palm Road 8950 Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club.

Pool

Kitchen

It's A Wonderful Life Vacay Home

3000 Salted Rim Rd, Kissimmee, Fl Kissimmee FL

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

Kitchen

Washer

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.

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

Nassau Point Trail 1621 Kissimmee FL

Located in Kissimmee, this cottage is within a 15-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club.

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

Kissimmee FL

Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center.

Pool

Kitchen

Don't see what you're looking for?

See all available properties in Windermere

View all properties

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.