Winter Park Vacation Rentals

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

Vacation Rentals in Winter Park

Grand Luxury Lakes 3BR Townhouse near Disney

Windermere FL

Located in Windermere (Horizon West), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Magic Kingdom® Park.

Kitchen

Washer

PRIVATE POOL/FREE RESORT ACCESS/CLOSE TO DISNEY/CLOSE TO RESTURANTS/MODERN STYLE

Bay Lake FL

With a stay at this vacation home in Lake Buena Vista (Bay Lake), you'll be a 1-minute drive from Walt Disney World® Resort and 7 minutes from Disney Springs™.

Pool

Kitchen

Magical Stay Near Universal Studios Florida

Orlando FL

With a stay at this vacation home in Orlando (Oak Ridge), you'll be within a 5-minute drive of Orlando International Premium Outlets and Mall at Millenia.

BBQ, Pool Days and Disney Nearby!

Kissimmee FL

With a stay at this vacation home in Kissimmee (Indian Wells), you'll be a 4-minute drive from Old Town and 10 minutes from Disney Springs™.

Pool

Kitchen

Experience Luxury in Your 11 En-Suites Mansion

Orlando FL

With a stay at this vacation home in Orlando, you'll be a 5-minute drive from Aquatica and 6 minutes from Orange County Convention Center.

Pool

Hot Tub

Must-See Renovation! Stunning Accessible Pool - Prime Resort Disney Location!

Kissimmee FL

Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.

Pool

Kitchen

ORLANDO BUDGET FRIENDLY HOUSE/ PRIVATE POOL/SLEEPS UP TO 12/ CLOSE TO EVERYTHING

Orlando FL

With a stay at this vacation home, you'll be centrally located in Orlando, a 3-minute drive from Florida Mall and 9 minutes from Orlando International Premium Outlets.

Pool

Kitchen

Spectacular big house, 4 Bedrooms, private pool

Kissimmee FL

With a stay at this vacation home in Kissimmee (Veranda Palms), you'll be within a 15-minute drive of Old Town and Disney Springs™.

Pool

Kitchen

Mid-century Modern Villa w/ Pool Near Universal

Orlando FL

With a stay at this vacation home in Orlando, you'll be within a 5-minute drive of Universal Orlando Resort and Universal Studios Florida.

Orlando Vacation homeAway near Universal with hot/tub

Orlando FL

$209 nightly

$232 total

May 4 - May 5

Total with taxes and fees

With a stay at this vacation home in Orlando (Oak Ridge), you'll be a 4-minute drive from Orlando International Premium Outlets and 6 minutes from Universal Orlando Resort.

Luxury 6 bed South-Facing Pool, Game Room, 4 Miles to Disney World

Kissimmee FL

With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and Disney Springs™.

Pool

Hot Tub

Disney & Universal Getaway 4BR/3BA Pool Home Minutes to Parks!

Kissimmee FL

With a stay at this vacation home in Kissimmee (Veranda Palms), you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets.

Pool

Kitchen

Don't see what you're looking for?

See all available properties in Winter Park

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.