Book Holiday Homes in Winter Haven

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Featured Holiday Homes in Winter Haven

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
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
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
Save an average of 15% on thousands of hotels when you're signed in
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!
2022 Award @ Hosthub, Home Theater/Game Room/Harry Potter Rm Close to Disney

2022 Award @ Hosthub, Home Theater/Game Room/Harry Potter Rm Close to Disney

Reunion
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a water park. Popular attractions ESPN Wide World of Sports ...
2022 Award @ Hosthub, Home Theater/Game Room/Harry Potter Rm Close to Disney
Private pool - spa  wifi/ game room under AC 3 miles from Disney

Private pool - spa wifi/ game room under AC 3 miles from Disney

Kissimmee
Stay at this vacation home in Kissimmee. Enjoy an in-room coffeemaker, air conditioning, and a spa tub. Popular attractions Disney's Animal Kingdom® Theme Park ...
Private pool - spa wifi/ game room under AC 3 miles from Disney
Exquisite home with pool, lanai, game room, central AC, & washer/dryer

Exquisite home with pool, lanai, game room, central AC, & washer/dryer

Davenport
Book a stay at this family-friendly vacation home in Davenport. Enjoy private pools, a water park, and a fitness center. Popular attractions Disney's Animal ...
Exquisite home with pool, lanai, game room, central AC, & washer/dryer
Margaritaville Cottage, Private Pool, Near Disney!

Margaritaville Cottage, Private Pool, Near Disney!

4 out of 5
8004 Sandy Toes Way, Kissimmee, FL
Stay at this 4-star vacation home in Kissimmee. Enjoy free parking, private pools, and balconies. Popular attractions Disney's Animal Kingdom® Theme Park and ...
Margaritaville Cottage, Private Pool, Near Disney!
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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 Haven 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 Haven vacation homes are the perfect way for you to wing it.

Holiday houses in Winter Haven 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 Haven 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 Haven adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winter Haven 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 Haven 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 Haven Holiday Homes essential information

Accommodation
20502 Holiday Homes
Lowest Price
NZ$205
Highest Price
NZ$465
Popular accommodation
The Berkley, Orlando, Formosa Valley Resort by UNE Homes, Relaxing Oasis with Private Pool & Resort Perks, 25 OFF 200+5-star reviews.15 MIN TO DISNEY. CLEAN HOME IN PREMIUM LOCATION., Luxury Home - 5 Minutes From Disney - Star Wars Theatre!, 2022 Award @ Hosthub, Home Theater/Game Room/Harry Potter Rm Close to Disney, Private pool - spa wifi/ game room under AC 3 miles from Disney, Exquisite home with pool, lanai, game room, central AC, & washer/dryer, Margaritaville Cottage, Private Pool, Near Disney!

Top trending hotels in Winter Haven

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

3.5 out of 5
5801 Roosevelt Dr, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is NZ$304 per night from 23 Feb to 24 Feb
NZ$304
includes taxes & fees
23 Feb - 24 Feb
Stay at this 3.5-star business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Plus Winter Haven Inn & Suites 
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is NZ$224 per night from 24 Feb to 25 Feb
NZ$224
includes taxes & fees
24 Feb - 25 Feb
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Howard Johnson by Wyndham Winter Haven FL
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
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Vacation Village at Parkway

Vacation Village at Parkway

3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
The price is NZ$205 per night from 9 Mar to 10 Mar
NZ$205
includes taxes & fees
9 Mar - 10 Mar
Stay at this 3-star family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 spa tubs. Our guests praise the helpful staff and the clean rooms ...
Vacation Village at Parkway
Don't see what you're looking for?
See all available properties in Winter Haven
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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.