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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

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, (2950)
"Had every thing you would need for a family trip Perfect loved it "
The price is 2.446.501 ₫
3.225.536 ₫ total
includes taxes & fees
15 Oct - 16 Oct
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, (1651)
"It was a great stay !"
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, (5639)
"There are a lot of activities that we enjoyed while staying here. Very nice and clean resort. "
The price is 2.845.908 ₫
4.036.446 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Summer Bay Orlando by Exploria Resorts
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1937)
"Great stay!"
The price is 3.331.082 ₫
4.046.552 ₫ total
includes taxes & fees
12 Oct - 13 Oct
The Berkley, Orlando
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1410)
"amazing place for families"
Reunion Resort & Golf Club
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, (2986)
"Loved the location of the property and that the property was gated"
Regal Oaks Resort Vacation Townhomes by IDILIQ
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, (1385)
"The unit was great for our large group of people. The only issue was some cheaply made furniture that seemed very wobbly. "
Encantada Resort Vacation Townhomes by IDILIQ
Magical Dreams
Outdoor pool

Magical Dreams

4.0 star property
10.0 out of 10, Exceptional, (1)
"estaba algo caliente pero nos contactamos con los encargados y nos solucionaron el problema "
The price is 1.449.305 ₫
3.439.464 ₫ total
includes taxes & fees
11 Oct - 12 Oct
Magical Dreams
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (147)
"Loved being able to walk across the street to Old Town. Large space and a great price. "
The price is 2.535.941 ₫
3.207.285 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Barefoot'n Resort Kissimmee Orlando
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, (1146)
"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, (141)
"Amber was great we had a ball definitely coming back resort was beautiful "
Grand Lake Resort
Barefoot Suites
Dock

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1772)
"Much better than the last stay there!"
Barefoot Suites
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, (491)
"Quiet environment "
The price is 2.741.648 ₫
3.470.821 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Lifetime of Vacations Resort
Lake view

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (147)
"Quiet place "
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, (171)
"Great stay"
Formosa Valley Resort by UNE Homes
Royal Laguna Villas By Magical Memories
Lobby

Royal Laguna Villas By Magical Memories

3.5 star property
7.0 out of 10, Good, (2336)
"the apartment is comfortable and pleasant but the air conditioning does not work, there is only a ceiling fan in the main room and in the living room. They did not give us the card for the pool area and it was a problem to pay and get the lockbox code."
Royal Laguna Villas By Magical Memories
Summerville Vacation Homes by Columbia Management
Captiva-06 (SMV104) | Private kitchen | Fridge, microwave, oven, stovetop

Summerville Vacation Homes by Columbia Management

4.0 star property
8.4 out of 10, Very good, (152)
"Not enough parking "
Summerville Vacation Homes by Columbia Management
Encore Resort
Outdoor pool

Encore Resort

4.0 star property
6.4 out of 10, (117)
"Great place "
Encore Resort
Villas At Regal Palms
Outdoor pool, pool loungers

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very good, (579)
"This was the 2nd time we’ve stayed at Regal Palms and will definitely be back again. "
Villas At Regal Palms
Caribe Cove Resort
Outdoor pool, a heated pool

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2258)
"We had a great family vacation "
Caribe Cove 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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Top Winter Haven Hotel Reviews

Meliá Orlando Celebration

Meliá Orlando Celebration

10/10 Excellent
"Excellent "
debbie 4-night trip
Posted 3 days ago
Meliá Orlando Celebration

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 128 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 Indigo's Family Fun Center, 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.