Book Holiday Homes in Winter Garden

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Featured Holiday Homes in Winter Garden

The Berkley, Orlando

The Berkley, Orlando

4 out of 5
8545 W. Irlo Bronson Highway, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is AU$341 per night from 24 Apr to 25 Apr
AU$341
includes taxes & fees
24 Apr - 25 Apr
With a stay at The Berkley, Orlando in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center.
The Berkley, Orlando
Marriott's Sabal Palms

Marriott's Sabal Palms

4 out of 5
8805 World Center Dr, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is AU$385 per night from 27 Apr to 28 Apr
AU$385
includes taxes & fees
27 Apr - 28 Apr
Located in Orlando, Marriott's Sabal Palms is within a 15-minute drive of Disney's Hollywood Studios® and Aquatica.
Marriott's Sabal Palms
Maple Leaf Inn & Suites

Maple Leaf Inn & Suites

2.5 out of 5
Kissimmee
The price is AU$110 per night from 1 Apr to 2 Apr
AU$110
includes taxes & fees
1 Apr - 2 Apr
With a stay at Maple Leaf Inn & Suites in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets.
Maple Leaf Inn & Suites
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Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes

4 out of 5
Formosa Vly Pl, Kissimmee, FL
With a stay at Formosa Valley Resort by UNE Homes in Kissimmee, you'll be a 3-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® ...
Formosa Valley Resort by UNE Homes
Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney

Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney

Kissimmee
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town.
Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney
The Adventure of a Lifetime! 5 BDR in Desirable Windsor Island Resort Sleeps 14

The Adventure of a Lifetime! 5 BDR in Desirable Windsor Island Resort Sleeps 14

Davenport
With a stay at this vacation home, you'll be centrally located in Davenport, within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town ...
The Adventure of a Lifetime! 5 BDR in Desirable Windsor Island Resort Sleeps 14
Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando
The price is AU$303 per night from 14 Apr to 15 Apr
AU$303
includes taxes & fees
14 Apr - 15 Apr
Located in Orlando (Southern Oaks), this vacation home is within a 10-minute drive of Kia Center and Camping World Stadium.
Quiet Oasis in Lovely Neighborhood
Encore Resort

Encore Resort

4 out of 5
101 Lasso Drive, Kissimmee, FL
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Disney's Hollywood Studios®.
Encore Resort
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*

Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*

Davenport
With a stay at this vacation home in Davenport (West Haven), you'll be within a 15-minute drive of Old Town and ChampionsGate Golf Club.
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
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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.

Winter Garden Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winter Garden vacation homes are the perfect way for you to wing it.

Holiday houses in Winter Garden let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winter Garden in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winter Garden adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winter Garden with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winter Garden vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winter Garden Holiday Homes essential information

Accommodation
30430 Holiday Homes
Lowest Price
AU$110
Highest Price
AU$391
Popular accommodation
The Berkley, Orlando, Marriott's Sabal Palms, Maple Leaf Inn & Suites, Formosa Valley Resort by UNE Homes, Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney, The Adventure of a Lifetime! 5 BDR in Desirable Windsor Island Resort Sleeps 14, Quiet Oasis in Lovely Neighborhood, Encore Resort, Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*

Top trending hotels in Winter Garden

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$391 per night from 27 Apr to 28 Apr
AU$391
includes taxes & fees
27 Apr - 28 Apr
Located in Winter Garden, The Grove Resort & Water Park Orlando is on a lake, a 1-minute drive from Surfari Water Park and 11 minutes from Orange County National ...
The Grove Resort & Water Park Orlando
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$219 per night from 27 Apr to 28 Apr
AU$219
includes taxes & fees
27 Apr - 28 Apr
With a stay at Home2 Suites by Hilton Orlando at Flamingo Crossings in Winter Garden (Bay Lake), you'll be a 1-minute drive from Flamingo Crossings Town Center ...
Home2 Suites by Hilton Orlando at Flamingo Crossings
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

2.5 out of 5
631 FLAGLER AVE, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$208 per night from 20 Apr to 21 Apr
AU$208
includes taxes & fees
20 Apr - 21 Apr
Located in Winter Garden (Bay Lake), Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center is within a 15-minute drive of Walt Disney ...
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

4 out of 5
17777 Bali Blvd, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$250 per night from 29 Apr to 30 Apr
AU$250
includes taxes & fees
29 Apr - 30 Apr
Located in Winter Garden, Hilton Vacation Club Aqua Sol Orlando West is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club.
Hilton Vacation Club Aqua Sol Orlando West
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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.

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^Subject to availability and chosen travel dates.