Winter Park Vacation Rentals

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Vacation Rentals in Winter Park

Charming 3-bedroom house w/ AC in Kissimmee, nearby Disney, Walmart, Ross & more

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.

Hot Tub

Kitchen

NEW Private Pool Resort Home 10 Min Disney

Kissimmee FL

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

Pool

Kitchen

BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY... FULLY EQUIPED

kissimmee FL

When you stay at this vacation home in Kissimmee, you'll be on a lake, a 3-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets.

Pool

Kitchen

Beautiful 9-bedroom house with AC in serene Kissimmee , Bring the whole Family !

Kissimmee FL

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

Storey Lake Resort home with Mini-Golf & Lazy River | Private Pool | Sleeps 10

Kissimmee FL

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

Pool & BBQ - Disney-Themed Cozy 6BD - Near Disney

Kissimmee FL

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

Storey Lake - Private Pool Home 10 Min to Disney

Kissimmee FL

$338 nightly

$379 total

Aug 27 - Aug 28

Total with taxes and fees

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.

Pool

Kitchen

Entire guesthouse in Orlando, Florida

Orlando FL

$115 nightly

$127 total

Aug 27 - Aug 28

Total with taxes and fees

With a stay at this vacation home in Orlando (Tangelo Park), you'll be within a 5-minute drive of Orlando International Premium Outlets and The Orlando Eye.

Kitchen

Pet friendly

Beautiful Disney Home! Heated Pool/Spa • Arcade • Gated Community • 4BR / 3BA

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

Hot Tub

3 Bedroom 2 Bath Condo Disney area 8601

Orlando FL

$275 nightly

$275 total

Aug 27 - Aug 28

Total with taxes and fees

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

Lux 5BR Home w/Game Room, 4 Suites & Private Pool

Orlando FL

With a stay at this vacation home in Orlando, you'll be a 4-minute drive from Orange County Convention Center and 6 minutes from Orlando Vineland Premium Outlets.

A Home Where Eclectic Luxury Meets Affordability

Altamonte Springs FL

A stay at this vacation home places you in the heart of Altamonte Springs, within a 5-minute drive of Altamonte Mall and Cranes Roost Park.

Kitchen

Washer

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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.