Winter Garden 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 Garden hotels

Vacation Rentals in Winter Garden

The Berkley, Orlando

8545 W. Irlo Bronson Highway Kissimmee FL

$146 nightly

$164 total

Jun 14 - Jun 15

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

With a stay at The Berkley, Orlando in Kissimmee, you'll be within a 5-minute drive of Island H2O Live! and Flamingo Crossings Town Center.

Pool

Hot Tub

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

Pool, Hot Tub+Game Rm, Mins to Disney & Universal | Sunshine Ridge by AvantStay

Kissimmee FL

Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Island H2O Live!.

Pool

Hot Tub

Doppio Westside

2470 Santorini Drive Davenport FL

$458 nightly

$520 total

Jun 14 - Jun 15

Total with taxes and fees

With a stay at Doppio Westside in Four Corners, you'll be within a 10-minute drive of Island H2O Live! and Flamingo Crossings Town Center.

Pool

Kitchen

Lovely 4-bedroom house in nice Kissimmee Disney

Kissimmee FL

$337 nightly

$377 total

Jun 15 - Jun 16

Total with taxes and fees

With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort.

Disney 8BR Villa w/2 Arcades, 2 Theaters, Pool+Spa

Davenport FL

With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Island H2O Live!.

Pool

Hot Tub

Spacious 5-bedroom house, mins from Disney World & major attractions

Kissimmee FL

With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 8 minutes from Island H2O Live!.

Newly remodeled Town Home 7 in 2022, 1200 Sq ft, Next to SeaWorld

Orlando FL

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

Fabulous 4 bedroom 3 bath Villa with private Pool , Golf nearby

Davenport FL

With a stay at this vacation home in Davenport (Aylesbury), you'll be within a 15-minute drive of ChampionsGate Golf Club and Mystic Dunes Golf Club.

JUST RENOVATED!✦Spacious✦Clean✦Private True South Pool/Spa✦5 Miles to Disney

Kissimmee FL

$394 nightly

$441 total

Jun 21 - Jun 22

Total with taxes and fees

With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.

Pool

Hot Tub

Waterpark Inc-Private Pool & Spa-Star Wars Games Room-Themed Bedroom-Free Wifi

Kissimmee FL

Located in Lake Buena Vista (Bay Lake), this vacation home is steps from Walt Disney World® Resort and a 4-minute drive from Disney Springs™.

Luxury Pool Home | Sleeps 17 | Free Resort Access + Walk to Clubhouse | Themed Rooms | Garage

Davenport FL

With a stay at this vacation home, you'll be centrally located in Four Corners, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course.

Don't see what you're looking for?

See all available properties in Winter Garden

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.