Find Family Hotels in Winter Haven, FL

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Check availability on Winter Haven Family Hotels

Tonight
Dec 6 - Dec 7
Tomorrow
Dec 7 - Dec 8
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Top Winter Haven Family Hotels

Waterslide
Legoland Florida Hotel

Legoland Florida Hotel

3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (49)
"Really enjoyable stay. "
United Kingdom
John
The price is ￥57,243
￥70,193 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Legoland Florida Hotel
Bar (on property)
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (1002)
"Clean room, great staff, easy check-in."
United States
Vanessa
The price is ￥19,391
￥21,718 total
includes taxes & fees
Dec 22 - Dec 23
Holiday Inn Winter Haven by IHG
Exterior
Hampton Inn Winter Haven

Hampton Inn Winter Haven

2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1002)
"Clean room, staff was nice, breakfast was good, easy parking."
United States
Jessica
The price is ￥17,273
￥19,346 total
includes taxes & fees
Dec 14 - Dec 15
Hampton Inn Winter Haven
Blackout drapes, iron/ironing board, free cribs/infant beds
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
Winter Haven
7.0 out of 10, Good, (1001)
"Nice hotel. Clean and great location. "
United States
Raylene
The price is ￥13,186
￥14,767 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Howard Johnson by Wyndham Winter Haven FL
Property amenity
Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven

3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (730)
"Great staff, great location "
United States
katherine
The price is ￥25,629
￥28,705 total
includes taxes & fees
Dec 21 - Dec 22
Courtyard by Marriott Winter Haven
Game room
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (2)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is ￥17,840
￥43,708 total
includes taxes & fees
Dec 8 - Dec 9
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
4 bedrooms, desk, iron/ironing board, travel crib
The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia

2.0 star property
Winter Haven
9.6 out of 10, Exceptional, (8)
"Had a great time. Great location. Looking forward to my next visit. Great hosts as well. "
United States
James K.
The price is ￥18,616
￥46,136 total
includes taxes & fees
Dec 7 - Dec 8
The Old Haven - An Enduring Piece of Nostalgia
Game room
Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Winter Haven
9.8 out of 10, Exceptional, (39)
"We had a great stay!"
United States
Harper B.
The price is ￥18,150
￥49,213 total
includes taxes & fees
Dec 9 - Dec 10
Heated Pool and Hot tub-near Legoland, Disney, Theme parks
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)
"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 ￥26,527
￥67,987 total
includes taxes & fees
Dec 10 - Dec 11
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Fridge, microwave, oven, stovetop
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

Winter Haven
9.4 out of 10, Exceptional, (64)
"A pleasant stay"
United States
Andeelynn D.
The price is ￥19,407
￥43,610 total
includes taxes & fees
Dec 7 - Dec 8
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
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

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent
"Clean room, location, facilities "
Jeffry 6-night trip
Posted 3 days ago
Ramada by Wyndham Kissimmee Gateway

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Frequently asked questions

What's Winter Haven like for family-friendly vacations?
If you've been thinking about a vacation with your kids, Winter Haven is a good choice. The exciting theme parks, entertainment, and lake views are just some of the things that make this the perfect spot for family trips. Fly into Lakeland Intl. Airport (LAL), which is located 17.3 mi (27.8 km) from the city center.
What's the best accommodation for families in Winter Haven?
Legoland Florida Hotel is a hotel with a water park and 2 outdoor pools, and it's a top choice on Expedia for families. Other good choices for your stay with the kids include Howard Johnson by Wyndham Winter Haven FL and Hampton Inn Winter Haven.
When's the best time to book a family-friendly vacation in Winter Haven?
The hottest months are usually August and July with an average temp of 81°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Haven are August, July, September, and June, with each month seeing an average of 8 inches of rainfall.
What's there to see and do with your family in Winter Haven?
While you and your family are vacationing in Winter Haven, you might want to visit some family-friendly attractions such as LEGOLAND® Florida and Theatre Winter Haven. Make sure you have lots of time for activities like Chain of Lakes Park and Peppa Pig Theme Park Florida.
What's the best way for us to get around Winter Haven?
To see more of the larger area, hop aboard a train at Winter Haven Station. Winter Haven might not have very many public transit options to choose from so consider a car rental to maximize your time.