Family Hotels & Resorts in Winter Haven from NZ$163

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Check availability on Winter Haven Family Hotels

Tonight
28 Dec - 29 Dec
Tomorrow
29 Dec - 30 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Winter Haven family-friendly hotels

Waterslide
Legoland Florida Hotel

Legoland Florida Hotel

Legoland Florida Hotel
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (54)
"Really enjoyable stay. "
United Kingdom
John
The price is NZ$679
includes taxes & fees
6 Jan - 7 Jan 2026
Legoland Florida Hotel
Exterior
Hampton Inn Winter Haven

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 NZ$203
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Winter Haven
Blackout curtains, iron/ironing board, free cots/infant beds
Howard Johnson by Wyndham Winter Haven FL

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, (1002)
"Nice hotel. Clean and great location. "
United States
Raylene
The price is NZ$163
includes taxes & fees
31 Dec - 1 Jan 2026
Howard Johnson by Wyndham Winter Haven FL
Bar (on property)
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (1000)
"Was ok Regular Holiday inn experience Staff were nice "
United States
Nadav
The price is NZ$276
includes taxes & fees
12 Jan - 13 Jan 2026
Holiday Inn Winter Haven by IHG
Property amenity
Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (734)
"Great staff, great location "
United States
katherine
The price is NZ$332
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Winter Haven
Games room
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

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 NZ$481
includes taxes & fees
30 Dec - 31 Dec
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Fridge, microwave, oven, stovetop
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

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

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
Winter Haven
9.4 out of 10, Exceptional, (65)
"The accommodation at this property was exceptional. It felt safe, and was safe Parking was great, proximity to dinning and shopping was withing 5 minutes drive, and the location was peaceful and safe."
United States
Dwight
The price is NZ$485
includes taxes & fees
30 Dec - 31 Dec
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
House (3 Bedrooms) | Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

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 NZ$751
includes taxes & fees
3 Jan - 4 Jan 2026
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3 bedrooms, desk, iron/ironing board, travel cot
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
2.0 star property
Winter Haven
9.8 out of 10, Exceptional, (7)
"Great location, clean and great communication with hosts "
United States
Angie Y.
The price is NZ$535
includes taxes & fees
30 Dec - 31 Dec
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Smart TV
⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance

⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance

⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance
Winter Haven
10.0 out of 10, Exceptional, (3)
"The place was clean and tidy, accessible to a lot of stores and attractions in the surrounding area, and the hosts were SO nice and easy to contact throughout our stay-even checking in on us to make sure everything was going good. Would totally stay again!"
United States
Kaitlyn F.
The price is NZ$255
includes taxes & fees
28 Jan - 29 Jan 2026
⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance
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

Top Winter Haven Hotel Reviews

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent
"The staff was super helpful, the room was clean and quiet. Great location too!!!"
Robert 1-night trip
Posted 1 day ago
Holiday Inn Resort Kissimmee by the Parks by IHG

Frequently asked questions

What's Winter Haven like for family-friendly holidays?
If you've been thinking about a holiday with your children, 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 centre.
What's the best family accommodation 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 choices to stay with the children include Howard Johnson by Wyndham Winter Haven FL and Hampton Inn Winter Haven.
When's the best time to book a family-friendly holiday in Winter Haven?
The hottest months are usually August and July, with an average temperature of 27°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Haven are August, July, September and June, with each month seeing an average of 211 mm of rainfall.
What's there to see and do with your family in Winter Haven?
While you and your family are holidaying in Winter Haven, you may want to visit some family-friendly attractions such as LEGOLAND® Florida and Theatre Winter Haven. Make sure that you have lots of time for activities such as Chain of Lakes Park and Peppa Pig Theme Park Florida.
What's the best way for us to get around Winter Haven?
If you want to venture outside the area, hop on a train at Winter Haven Station. Winter Haven may not have many public transport choices, so consider a car rental to maximise your time.