Winter Park Cottages

Name: A curated stay in the Historic College Quarter
Address: Winter Park

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Cottages in Winter Park

Orlando Lakefront Tiny House Community

3405 N Orange Blossom Trail, Orlando, FL

$76

per night

May 19 - May 20

When you stay at Orlando Lakefront Tiny House Community in Orlando, you'll be on the waterfront, within a 10-minute drive of Camping World Stadium and Kia Center.

Pet friendly

Parking included

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

Parking included

Cottage II

$98

per night

May 19 - May 20

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

Fireplace

Free WiFi

Beautiful, Modern Home W/private Pool! Near WDW

4825 Dedication Street, Kissimmee, FL

With a stay at this cottage in Kissimmee, you'll be a 5-minute drive from Old Town and 9 minutes from Disney Springs™.

Pool

Parking included

Downtown Winter Garden Home ~ 12 Mi to Disney!

Located in Winter Garden, this cottage is within a 5-minute drive of West Orange Trail and Resurrection Catholic Church.

Quiet 1 bedroom Guest House with pool & WiFi Lake May, Florida

$125

per night

May 23 - May 24

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

Free WiFi

Downtown Winter Garden Cottage ~ 12 Mi to Disney!

With a stay at this cottage in Winter Garden, you'll be within a 5-minute drive of West Orange Trail and Resurrection Catholic Church.

Outdoor Space

Air conditioning

4214 Paragraph Drive

With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.

Pool

Parking included

Idyllic Sorrento Vacation Home w/ Patio & Grill

With a stay at this cottage in Sorrento, you'll be within a 15-minute drive of King's Landing and Kelly Park.

Parking included

Free WiFi

Orlando Home w/ Lake View, Pool & Game Room!

With a stay at this cottage in Kissimmee (Buena Ventura Lakes), you'll be within a 15-minute drive of Florida Mall and Austin-Tindall Regional Park.

Pool

Parking included

Luxurious Home W/private Pool, Near Disney!

3084 Juliet Drive, Kissimmee, FL

With a stay at this cottage in Kissimmee, you'll be a 5-minute drive from Old Town and 10 minutes from Disney Springs™.

A curated stay in the Historic College Quarter

With a stay at this cottage, you'll be centrally located in Winter Park, within a 10-minute drive of Kia Center and Camping World Stadium.

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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.