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 NZ$465 per night from 9 Mar to 10 Mar
NZ$465
includes taxes & fees
9 Mar - 10 Mar
Stay at this 4-star family-friendly vacation home in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the ...
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 NZ$625 per night from 16 Mar to 17 Mar
NZ$625
includes taxes & fees
16 Mar - 17 Mar
Stay at this 4-star business-friendly vacation home in Orlando. Enjoy free WiFi, a fitness center, and parking (surcharge). Popular attractions Disney Springs™ ...
Marriott's Sabal Palms
Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes

4 out of 5
Formosa Vly Pl, Kissimmee, FL
Stay at this 4-star vacation home in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Disney's Animal Kingdom® Theme Park and ...
Formosa Valley Resort by UNE Homes
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Vista Cay Resort by Casiola Vacation Homes

Vista Cay Resort by Casiola Vacation Homes

3.5 out of 5
4874 Cayview Ave, Orlando, FL
The price is NZ$828 per night from 25 Feb to 26 Feb
NZ$828
includes taxes & fees
25 Feb - 26 Feb
Stay at this 3.5-star family-friendly vacation home in Orlando. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Orlando International ...
Vista Cay Resort by Casiola Vacation Homes
Relaxing Oasis with Private Pool & Resort Perks

Relaxing Oasis with Private Pool & Resort Perks

Kissimmee
Stay at this vacation home in Kissimmee. Enjoy a water park, patios, and cable/satellite TV service. Popular attractions Disney's Animal Kingdom® Theme Park ...
Relaxing Oasis with Private Pool & Resort Perks
Maple Leaf Inn & Suites

Maple Leaf Inn & Suites

2.5 out of 5
Kissimmee
The price is NZ$156 per night from 25 Feb to 26 Feb
NZ$156
includes taxes & fees
25 Feb - 26 Feb
Stay at this vacation home in Kissimmee. Enjoy free WiFi, free parking, and room service. Popular attractions Disney Springs™ and ESPN Wide World of Sports are ...
Maple Leaf Inn & Suites
Marriott's Imperial Palm Villas

Marriott's Imperial Palm Villas

4 out of 5
8404 Vacation Way, Orlando, FL
The price is NZ$841 per night from 25 Feb to 26 Feb
NZ$841
includes taxes & fees
25 Feb - 26 Feb
Stay at this 4-star eco-certified vacation home in Orlando. Enjoy free WiFi, a fitness center, and parking (surcharge). Popular attractions Disney Springs™ and ...
Marriott's Imperial Palm Villas
25 OFF 200+5-star reviews.15 MIN TO DISNEY. CLEAN HOME IN PREMIUM LOCATION.

25 OFF 200+5-star reviews.15 MIN TO DISNEY. CLEAN HOME IN PREMIUM LOCATION.

Davenport
Book a stay at this golf vacation home in Davenport. Enjoy free WiFi, private pools, and a water park. Our guests praise the pool and the helpful staff in our ...
25 OFF 200+5-star reviews.15 MIN TO DISNEY. CLEAN HOME IN PREMIUM LOCATION.
Luxury  Home - 5 Minutes From Disney - Star Wars Theatre!

Luxury Home - 5 Minutes From Disney - Star Wars Theatre!

Kissimmee
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a water park. Popular attractions Disney's Animal Kingdom® ...
Luxury Home - 5 Minutes From Disney - Star Wars Theatre!
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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
25686 Holiday Homes
Lowest Price
NZ$156
Highest Price
NZ$841
Popular accommodation
The Berkley, Orlando, Marriott's Sabal Palms, Formosa Valley Resort by UNE Homes, Vista Cay Resort by Casiola Vacation Homes, Relaxing Oasis with Private Pool & Resort Perks, Maple Leaf Inn & Suites, Marriott's Imperial Palm Villas, 25 OFF 200+5-star reviews.15 MIN TO DISNEY. CLEAN HOME IN PREMIUM LOCATION., Luxury Home - 5 Minutes From Disney - Star Wars Theatre!

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 NZ$342 per night from 23 Mar to 24 Mar
NZ$342
includes taxes & fees
23 Mar - 24 Mar
Stay at this 4-star spa resort in Four Corners. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
The Grove Resort & Water Park Orlando
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 NZ$263 per night from 11 Mar to 12 Mar
NZ$263
includes taxes & fees
11 Mar - 12 Mar
Book a stay at this business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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 NZ$274 per night from 20 Mar to 21 Mar
NZ$274
includes taxes & fees
20 Mar - 21 Mar
Stay at this 3-star business-friendly hotel in Winter Garden. Enjoy free breakfast, a free theme park shuttle, and a 24-hour fitness center. Our guests praise ...
Home2 Suites by Hilton Orlando at Flamingo Crossings
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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 NZ$303 per night from 26 Feb to 27 Feb
NZ$303
includes taxes & fees
26 Feb - 27 Feb
Stay at this 4-star family-friendly hotel in Four Corners. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
Hilton Vacation Club Aqua Sol Orlando West
Don't see what you're looking for?
See all available properties in Winter Garden
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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.