Winter Park Villas

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

Check dates for Winter Park hotels

Villas in Winter Park

Modern Luxury Villa with Everything

Kissimmee FL

With a stay at this villa in Kissimmee, you'll be a 5-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets.

Pool

Kitchen

Ultimate Lakeview Villa with Everything!

Kissimmee FL

When you stay at this villa in Kissimmee, you'll be on a lake, a 5-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets.

Pool

Kitchen

Modern Luxury Villa with Everything

Kissimmee FL

When you stay at this villa in Kissimmee, you'll be on a lake, a 5-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets.

Pool

Kitchen

Lakeview Luxury Villa with Everything!

Kissimmee FL

When you stay at this villa in Kissimmee, you'll be on the waterfront, a 5-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets.

Pool

Kitchen

Close to Disney and Universal

KISSIMMEE FL

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

Pool

Hot Tub

Lakeview Luxury Villa with Everything

Kissimmee FL

When you stay at this villa in Kissimmee, you'll be on a lake, a 5-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets.

Pool

Kitchen

6277SK-New Brand-12bed/11.5bath-Private Pool&SPA

Orlando FL

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

Pool

Hot Tub

Unbeatable Location: Your Dream Villa Next to SeaWorld

Orlando FL

With a stay at this villa in Orlando (International Drive District), you'll be within a 5-minute drive of Aquatica and Orlando Vineland Premium Outlets.

Pool

Hot Tub

Lakeview Luxury Villa in Storey Lake

Kissimmee FL

When you stay at this villa in Kissimmee, you'll be on a lake, within a 15-minute drive of Old Town and Disney Springs™.

Pool

Hot Tub

180 Degree Water Views. No rear Neighbours. Games Rm. Spa. Cinema Star Wars.

Kissimmee FL

When you stay at this villa in Kissimmee, you'll be on a lake, within a 15-minute drive of Old Town and Disney Springs™.

Pool

Hot Tub

7BR Lakefront Duplex w/ Pool, Sauna & Hot Tub!

Orlando FL

$528 nightly

$586 total

Dec 14 - Dec 15

Total with taxes and fees

Located in Orlando (Edgewood), this villa is within a 10-minute drive of Kia Center and Florida Mall.

Pool

Hot Tub

Lakeview Luxury Villa with Everything!

Kissimmee FL

When you stay at this villa in Kissimmee, you'll be on a lake, a 5-minute drive from Old Town and 8 minutes from 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.