Book Holiday Homes in Winter Haven

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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
Holiday Homes
Lowest Price
AU$198
Highest Price
AU$367
Popular accommodation
Best Western Plus Winter Haven Inn & Suites , Howard Johnson by Wyndham Winter Haven FL, The Grove Resort & Water Park Orlando, Hilton Vacation Club Mystic Dunes Orlando

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$240 per night from 2 Feb to 3 Feb
AU$240
includes taxes & fees
2 Feb - 3 Feb
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, Cypress Gardens & US 17 South, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is AU$198 per night from 3 Feb to 4 Feb
AU$198
includes taxes & fees
3 Feb - 4 Feb
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
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$367 per night from 9 Feb to 10 Feb
AU$367
includes taxes & fees
9 Feb - 10 Feb
Located in Four Corners, 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
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Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 3 Mar to 4 Mar
AU$225
includes taxes & fees
3 Mar - 4 Mar
Located in Kissimmee, Hilton Vacation Club Mystic Dunes Orlando is within a 15-minute drive of Disney's Hollywood Studios® and Disney Springs™.
Hilton Vacation Club Mystic Dunes Orlando
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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.