Winter Park Cottages

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Cottages in Winter Park

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

Orlando FL

$319 nightly

$354 total

Jul 13 - Jul 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.

INSTANT BOOK • PRIVATE POOL PARADISE • NIGHT SWIMS

Lake Mary FL

$254 nightly

$281 total

Jun 30 - Jul 1

Total with taxes and fees

With a stay at this cottage in Lake Mary, you'll be within a 15-minute drive of Wekiwa Springs State Park and Lake Mary Farmer's Market.

Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,

Altamonte Springs FL

With a stay at this cottage in Altamonte Springs, you'll be within a 15-minute drive of Wekiwa Springs State Park and AdventHealth Altamonte Springs.

Relax Tonight. Cozy, Quiet and Super Clean.

Lake Mary FL

$210 nightly

$233 total

Jun 22 - Jun 23

Total with taxes and fees

With a stay at this cottage in Lake Mary, you'll be within a 15-minute drive of Wekiwa Springs State Park and Lake Mary Farmer's Market.

Incredible Private Lakefront Cottage Retreat

Altamonte Springs FL

$339 nightly

$375 total

Jul 16 - Jul 17

Total with taxes and fees

When you stay at this cottage in Altamonte Springs, you'll be on the waterfront, within a 15-minute drive of Kia Center and Wekiwa Springs State Park.

Tiny Hidden Cottage

Longwood FL

With a stay at this cottage in Longwood, you'll be within a 15-minute drive of Wekiwa Springs State Park and Altamonte Mall.

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.

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 Orlando Vineland Premium Outlets and Disney Springs™.

4177 Paragraph Drive

4177 Paragraph Drive Kissimmee FL

Located in Kissimmee, this cottage is within a 15-minute drive of Disney Springs™ and Disney's Typhoon Lagoon Water Park.

16 Mi to Disney: Cottage w/ Deck in Winter Garden

Winter Garden FL

With a stay at this cottage in Winter Garden, you'll be within a 15-minute walk of Winter Garden Art Association and Winter Garden Heritage Museum.

Stunning 5BR Home - Your Dream Getaway

Bookmark Drive 2761 Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Orlando Vineland Premium Outlets and Old Town.

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 Orlando Vineland Premium Outlets and Old Town.

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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.