Windermere Cottages

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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

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

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

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

Our Retro Mod Pod-Disney & Old Town Minutes Away!

Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be a 3-minute drive from Old Town and 10 minutes from Walt Disney World® Resort.

Pool

Hot Tub

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™.

Pool

Kitchen

Tiny house close to Disney KISSIMMEE

Kissimmee FL

$155 nightly

$173 total

Dec 7 - Dec 8

Total with taxes and fees

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

Private Lakefront Cottage, Bright, Peaceful, and Perfect for a Relaxing Escape.

Clermont FL

When you stay at this cottage in Clermont, you'll be on the waterfront, within a 5-minute drive of Sanctuary Ridge Golf Club and Clermont National.

Kitchen

Washer

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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.