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Check prices for these dates

Tonight
24 Jun - 25 Jun
Tomorrow
25 Jun - 26 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Top Holiday Rentals in Winter Haven

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2275)
"We really enjoyed the place "
Vacation Village at Parkway
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1439)
"Nice family resort with everything you need within walking distance...."
The price is 11.305.577 ₫
19.398.857 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Summer Bay Orlando by Exploria Resorts
5 outdoor pools, pool umbrellas, pool loungers

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5482)
"Perfect and would stay again "
Summer Bay Orlando by Exploria Resorts
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1312)
"We had a fantastic time, enjoyed our stay and will definitely go back again"
Reunion Resort & Golf Club
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1808)
"Definitely would recommend and be staying again"
The price is 3.009.216 ₫
3.682.680 ₫ total
includes taxes & fees
30 Jun - 1 Jul
The Berkley, Orlando
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (109)
"Great place, would definitely stay there again "
The price is 3.171.781 ₫
3.926.217 ₫ total
includes taxes & fees
2 Jul - 3 Jul
Barefoot'n Resort Kissimmee Orlando
Regal Oaks Resort Vacation Townhomes by IDILIQ
View from property

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2922)
"We enjoy our stay "
Regal Oaks Resort Vacation Townhomes by IDILIQ
Villas At Regal Palms
Outdoor pool, pool loungers

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very good, (554)
"Great accomodation"
Villas At Regal Palms
Magic Village Yards, Trademark Collection by Wyndham
Outdoor pool, pool umbrellas, pool loungers

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1142)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham
Grand Lake Resort
Dock

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (125)
"Always a great place to stay"
Grand Lake Resort
Lifetime of Vacations Resort
Lake view

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (136)
"Rooms and Location"
Lifetime of Vacations Resort
Formosa Valley Resort by UNE Homes
Private pool

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (156)
"Second time we stayed in this place. Spacious, clean and convenient."
The price is 4.938.759 ₫
13.981.313 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Formosa Valley Resort by UNE Homes
Barefoot Suites
Aerial view

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1753)
"Much better than the last stay there!"
Barefoot Suites
Encantada Resort Vacation Townhomes by IDILIQ
2 outdoor pools, pool umbrellas, pool loungers

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1352)
"Stayed here 2 years in a row & we love the location & everything about the property! Staff is friendly. Definitely coming back in the future! "
Encantada Resort Vacation Townhomes by IDILIQ
Berkley Lake Townhomes
2 outdoor pools, a heated pool, open 8:00 AM to 7:00 PM, pool loungers

Berkley Lake Townhomes

3.0 star property
8.4 out of 10, Very good, (431)
"My kids love it "
Berkley Lake Townhomes
Encore Resort
Outdoor pool

Encore Resort

4.0 star property
6.4 out of 10, (117)
"Great place "
Encore Resort
Champions Gate condos by UNE
2 outdoor pools

Champions Gate condos by UNE

4.0 star property
8.8 out of 10, Excellent, (15)
"It was a great place to stay"
Champions Gate condos by UNE
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
2 outdoor pools, open 8 AM to 10 PM, pool loungers

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

3.5 star property
9.2 out of 10, Wonderful, (467)
"AL at the front desk ensured our stay was awesome, our rooms were clean and we felt safe. We enjoyed our stay. "
The price is 2.855.255 ₫
3.595.526 ₫ total
includes taxes & fees
25 Jun - 26 Jun
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Caribe Cove Resort
Outdoor pool, a heated pool

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2251)
"Everything was lovely "
Caribe Cove Resort
The Azur Resort
Townhome, 6 Bedrooms | View from room

The Azur Resort

4.0 star property
8.4 out of 10, Very good, (35)
"everything is very clean stores and dining are nearby"
The Azur Resort
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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Frequently asked questions

Can I find a holiday rental in Winter Haven?

Yes, there are holiday rentals in Winter Haven close to LEGOLAND® Florida, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Winter Haven speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave time to check out the gardens and entertainment venues during your visit.

How many holiday rentals are there in Winter Haven?

Choose from 145 Expedia holiday rentals in Winter Haven for a memorable holiday.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Peppa Pig Theme Park Florida, whereas The Circle B Bar Reserve and Rotary Park are a couple of great spots to enjoy the outdoors. Theatre Winter Haven and Chain of Lakes Park are other places to visit while you're in town.

What are holiday rentals like in Winter Haven?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Haven. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.