Book Holiday Homes in Winter Haven

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

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$344 per night from 5 May to 6 May
NZ$344
includes taxes & fees
5 May - 6 May
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
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
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 ...
Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney
Save an average of 15% on thousands of hotels when you're signed in
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
Book a stay at this family-friendly vacation home in Davenport. Enjoy private pools, a fitness center, and a garden. Popular attractions Disney's Animal Kingdom® ...
The Adventure of a Lifetime! 5 BDR in Desirable Windsor Island Resort Sleeps 14
Encore Resort

Encore Resort

4 out of 5
101 Lasso Drive, Kissimmee, FL
Stay at this 4-star vacation home in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions ESPN Wide World of Sports and Disney's ...
Encore Resort
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*

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

Davenport
Book a stay at this family-friendly vacation home in Davenport. Enjoy free WiFi, private pools, and a water park. Popular attractions ChampionsGate Golf Club ...
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
Tropical villa overlooking the lake with a private pool, spa, grill, & AC

Tropical villa overlooking the lake with a private pool, spa, grill, & AC

Kissimmee
Stay at this vacation home in Kissimmee. Enjoy private pools, a water park, and patios. Popular attractions Old Town and Give Kids the World Village are located ...
Tropical villa overlooking the lake with a private pool, spa, grill, & AC
Single Story, Private Pool, Water Views, Game Room | Sleeps 11

Single Story, Private Pool, Water Views, Game Room | Sleeps 11

Kissimmee
Stay at this vacation home in Kissimmee. Enjoy private pools, a pool table, and patios. Popular attractions Old Town and Give Kids the World Village are located ...
Single Story, Private Pool, Water Views, Game Room | Sleeps 11
 ALWAYS FREE POOL AND SPA HEAT - Disney fireworks from pool/spa, Orange grove

ALWAYS FREE POOL AND SPA HEAT - Disney fireworks from pool/spa, Orange grove

Davenport
Book a stay at this family-friendly vacation home in Davenport. Enjoy free WiFi, private pools, and 2 outdoor pickleball courts. Our guests praise the pool in ...
ALWAYS FREE POOL AND SPA HEAT - Disney fireworks from pool/spa, Orange grove
Don't see what you're looking for?
See all available properties in Winter Haven
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.

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
24363 Holiday Homes
Lowest Price
NZ$197
Highest Price
NZ$344
Popular accommodation
The Berkley, Orlando, 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, Encore Resort, Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*, Tropical villa overlooking the lake with a private pool, spa, grill, & AC, Single Story, Private Pool, Water Views, Game Room | Sleeps 11, ALWAYS FREE POOL AND SPA HEAT - Disney fireworks from pool/spa, Orange grove

Top trending hotels in Winter Haven

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard, Winter Haven, FL
Fully refundable
The price is NZ$255 per night from 28 Apr to 29 Apr
NZ$255
includes taxes & fees
28 Apr - 29 Apr
Stay at this 3-star business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful ...
Holiday Inn Winter Haven by IHG
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$292 per night from 1 May to 2 May
NZ$292
includes taxes & fees
1 May - 2 May
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, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is NZ$197 per night from 7 Apr to 8 Apr
NZ$197
includes taxes & fees
7 Apr - 8 Apr
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
Save an average of 15% on thousands of hotels when you're signed in
Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven

3 out of 5
6015 Cypress Gardens Blvd, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is NZ$265 per night from 20 Apr to 21 Apr
NZ$265
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3-star business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Chain ...
Home2 Suites By Hilton Winter Haven
Don't see what you're looking for?
See all available properties in Winter Haven
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.