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

Check dates for Winter Park hotels

Vacation Rentals in Winter Park

Marriott's Sabal Palms

8805 World Center Dr Orlando FL

$255 nightly

$287 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

Located in Orlando, Marriott's Sabal Palms is within a 15-minute drive of Disney's Hollywood Studios® and Aquatica.

Pool

Hot Tub

Vista Cay Resort by Casiola Vacation Homes

4874 Cayview Ave Orlando FL

$400 nightly

$450 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

When you stay at Vista Cay Resort by Casiola Vacation Homes in Orlando, you'll be connected to the convention center, within a 5-minute drive of Orange County Convention Center and Aquatica.

Pool

Hot Tub

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

Westgate Blue Tree

12007 Cypress Run Dr Orlando FL

$281 nightly

$325 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

With a stay at this vacation home in Orlando, you'll be within a 5-minute drive of Disney Springs™ and Orlando Vineland Premium Outlets.

Pool

Kitchen

Marriott's Imperial Palm Villas

8404 Vacation Way Orlando FL

$351 nightly

$395 total

Jan 3 - Jan 4, 2026

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

When you stay at Marriott's Imperial Palm Villas in Orlando, you'll be next to a golf course, within a 10-minute drive of Old Town and Walt Disney World® Resort.

Pool

Hot Tub

Amazing Breathtaking Fantasy World Newly Renovated Near Disney 2+2

Kissimmee FL

With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets.

Pool

Hot Tub

PentHouse Suite with 2X View

Orlando FL

$228 nightly

$254 total

Jan 8 - Jan 9, 2026

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Orlando, a 3-minute drive from Orlando Vineland Premium Outlets and 5 minutes from Disney Springs™.

Pool

Hot Tub

Storey Lake-CLOSEST RESORT TO DISNEY-FREE RESORT FACILITIES -MODERN-FREE WIFI

Kissimmee FL

With a stay at this vacation home in Lake Buena Vista (Bay Lake), you'll be a 4-minute walk from Walt Disney World® Resort and within a 5-minute drive of Disney Springs™.

Luxury Family Home! Kid Themed Rooms, Free Wifi, Waterpark, Jacuzzi, BBQ Grill!

Kissimmee FL

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

4846-Epic Home: 3 Suites at Vista Cay Resort

Orlando FL

$355 nightly

$395 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this vacation home in Orlando, you'll be within a 5-minute drive of Orange County Convention Center and Pointe Orlando.

Pool

Kitchen

Charming 3-bedroom near Orlando theme parks, downtown and golf courses

Casselberry FL

With a stay at this vacation home in Casselberry, you'll be within a 10-minute drive of Secret Lake Park and Red Bug Lake Park.

Upstay: Resort Retreat w Private Pool & BBQ area

Kissimmee FL

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

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.