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 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
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
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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
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!*
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
With a stay at this vacation home in Kissimmee (Cumbrian Lakes), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.
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
With a stay at this vacation home in Kissimmee (Cumbrian Lakes), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.
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
Located in Davenport, this vacation home is in a rural location, a 3-minute drive from Highland Reserve Golf Club and 6 minutes from Lake Davenport.
ALWAYS FREE POOL AND SPA HEAT - Disney fireworks from pool/spa, Orange grove
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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
24337 Holiday Homes
Lowest Price
AU$181
Highest Price
AU$369
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

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 AU$271 per night from 16 Apr to 17 Apr
AU$271
includes taxes & fees
16 Apr - 17 Apr
With a stay at Best Western Plus Winter Haven Inn & Suites  in Winter Haven, you'll be within a 5-minute drive of LEGOLAND® Florida and Chain Of Wakes.
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 AU$181 per night from 6 Apr to 7 Apr
AU$181
includes taxes & fees
6 Apr - 7 Apr
When you stay at Howard Johnson by Wyndham Winter Haven FL in Winter Haven, you'll be in the business district, within a 5-minute drive of Chain of Lakes Park ...
Howard Johnson by Wyndham Winter Haven FL
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 AU$240 per night from 20 Apr to 21 Apr
AU$240
includes taxes & fees
20 Apr - 21 Apr
With a stay at Home2 Suites By Hilton Winter Haven in Winter Haven, you'll be within a 15-minute walk of LEGOLAND® Florida and Chain Of Wakes.
Home2 Suites By Hilton Winter Haven
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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$369 per night from 28 Apr to 29 Apr
AU$369
includes taxes & fees
28 Apr - 29 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
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.