Search Holiday Rentals in Winter Haven

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Winter Haven holiday rentals

Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"House was great, perfect central location. Very quiet neighborhood nice farm outside peaceful back yard seating area. "
United States
Wade
The price is 2.103.975 ₫
7.098.448 ₫ total
includes taxes & fees
1 Mar - 2 Mar
BlockHaven near Legoland & Disney
House (3 Bedrooms) | Interior

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"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 4.440.186 ₫
11.379.859 ₫ total
includes taxes & fees
9 Feb - 10 Feb
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Outdoor pool, pool umbrellas, pool loungers

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (188 reviews)
"We have stayed here several times. "
United States
Martha
The price is 1.947.450 ₫
2.181.144 ₫ total
includes taxes & fees
10 Feb - 11 Feb
Lake Ida Beach 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent
"N/a"
Jennifer 1-night trip
Posted 11 hours ago
Ramada by Wyndham Kissimmee Gateway

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 71 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.