Search Holiday Rentals in Winter Haven

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Winter Haven holiday rentals

Outdoor pool, pool umbrellas, pool loungers
Lake Ida Beach Resort

Cottage in Winter Haven

Lake Ida Beach Resort
3.0 star property
7.2 out of 10, Good, (187)
"We have stayed here several times. "
United States
Martha
Lake Ida Beach Resort
House (3 Bedrooms) | Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Cottage in Winter Haven

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
10.0 out of 10, Exceptional, (3)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
United States
John
The price is 4.502.601 ₫
11.539.824 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors
BlockHaven near Legoland & Disney

Holiday Home in Winter Haven

BlockHaven near Legoland & Disney
3.5 star property
The price is 3.792.816 ₫
9.056.402 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
BlockHaven near Legoland & Disney
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

Margaritaville Resort Orlando

Margaritaville Resort Orlando

10/10 Excellent
"Loved the decor of the king suite overlooking the pool. The balcony was very spacious with 2 lawn chairs and 2 chaise loungers. The room was perfect for my significant other and me. Having a microwave in the room would have been helpful but not a deal breaker. The staff was very friendly and helpful. They did not hesitate to give us an upgrade from the king resort view room when asked."
EVELYN 1-night trip
Posted 1 day ago
Margaritaville Resort Orlando

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 61 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.