TOP Family Friendly Hotels in Winter Haven for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels | Expedia Singapore

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Check availability on Winter Haven Family friendly Hotels

Tonight

11 Oct - 12 Oct

Tomorrow

12 Oct - 13 Oct

Next weekend

16 Oct - 18 Oct

In two weeks

23 Oct - 25 Oct

Our top choices for Winter Haven family-friendly hotels

A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.

A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.

A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.

A modern hotel with a prominent entrance, multiple floors, and a parking lot.

1. Best Western Plus Winter Haven Inn & Suites

Winter Haven

S$187

includes taxes & fees

18 Oct - 19 Oct

A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".

A hotel lobby with a reception desk, seating area, and a bar.

A modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.

A hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.

2. Hampton Inn Winter Haven

Winter Haven

Family fun flourishes near LEGOLAND® Florida with free breakfast, cots, and a serene outdoor pool for enjoyable escapes.

S$169

includes taxes & fees

8 Nov - 9 Nov

An outdoor patio with a fire pit, wicker furniture, and a view of a lake.

A modern reception area with wooden panel walls and two reception desks.

A modern building with a large glass entrance, palm trees, and people walking around.

A Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.

3. Courtyard by Marriott Winter Haven

Winter Haven

S$206

includes taxes & fees

18 Oct - 19 Oct

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

A modern hotel room with a kitchenette, a dining area, and a bed.

A spacious, modern living area with a herringbone wood floor, a dining area with a wooden table and chairs, and a kitchen in the background.

A modern kitchen with a dining area, a flat-screen TV, and a large window.

4. Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

S$192

includes taxes & fees

18 Oct - 19 Oct

A hotel room with two beds, a desk, a television, and a door leading to another room.

A bathroom with a shower, a toilet, a sink, and a mirror.

A swimming pool with a poolside area, including lounge chairs and umbrellas, adjacent to a building with multiple windows and a brick facade.

A hotel dining area with multiple tables and chairs, ceiling lights, and artwork on the walls.

5. Holiday Inn Winter Haven by IHG

Winter Haven

Holiday inn creates memorable family moments with outdoor pool, proximity to legoland, and kid-friendly amenities.

S$159

includes taxes & fees

8 Nov - 9 Nov

A swimming pool area with people playing with building blocks.

A colorful LEGO-themed beach retreat sign with a beach house and a gas station in the background.

A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.

A colorful play structure with a lighthouse in the background.

6. LEGOLAND Beach Retreat

Winter Haven

S$293

includes taxes & fees

12 Oct - 13 Oct

An outdoor seating area with sofas, chairs, and a fire pit.

A hotel room with a desk, chair, sofa, ottoman, and a large window.

A modern bathroom with a glass shower enclosure, a white toilet, a vanity with a mirror, and a sink.

A modern lounge area with green upholstered chairs, a herringbone-patterned floor, and a large window providing natural light.

7. Home2 Suites By Hilton Winter Haven

Winter Haven

S$218

includes taxes & fees

1 Nov - 2 Nov

A hotel room with two beds, a TV, a microwave, and a desk with a lamp.

A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.

A restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.

A bathtub with a white shower curtain, a grab bar, and a handheld showerhead.

8. Howard Johnson by Wyndham Winter Haven FL

Winter Haven

Family fun near LEGOLAND® Florida—this welcoming hotel offers a gated outdoor pool, convenient location, and complimentary breakfast.

S$110

includes taxes & fees

18 Oct - 19 Oct

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Choose what matters most at family-friendly hotels in Winter Haven

Breakfast included

Pool

4 stars

Water park

All-inclusive

Family-friendly hotels with free breakfast in Winter Haven

A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.

A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.

A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.

A modern hotel with a prominent entrance, multiple floors, and a parking lot.

Best Western Plus Winter Haven Inn & Suites

Winter Haven

S$187

includes taxes & fees

18 Oct - 19 Oct

A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".

A hotel lobby with a reception desk, seating area, and a bar.

A hotel room with two beds, a large mirror, a wooden floor, and a view of the outdoors.

A hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.

Hampton Inn Winter Haven

Winter Haven

S$169

includes taxes & fees

8 Nov - 9 Nov

An outdoor patio with a fire pit, wicker furniture, and a view of a lake.

A modern hotel lobby with a long reception desk, bar area, and seating arrangement.

A Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.

A modern reception area with wooden panel walls and two reception desks.

Courtyard by Marriott Winter Haven

Winter Haven

S$206

includes taxes & fees

18 Oct - 19 Oct

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

A modern hotel room with a kitchenette, a dining area, and a bed.

A spacious, modern living area with a herringbone wood floor, a dining area with a wooden table and chairs, and a kitchen in the background.

A modern kitchen with a dining area, a flat-screen TV, and a large window.

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

S$192

includes taxes & fees

18 Oct - 19 Oct

A hotel room with two beds, a desk, a television, and a door leading to another room.

A hotel room with a desk, chair, sofa, and a painting on the wall.

A swimming pool with a poolside area, including lounge chairs and umbrellas, adjacent to a building with multiple windows and a brick facade.

A hotel dining area with multiple tables and chairs, ceiling lights, and artwork on the walls.

Holiday Inn Winter Haven by IHG

Winter Haven

S$159

includes taxes & fees

8 Nov - 9 Nov

An outdoor seating area with sofas, chairs, and a fire pit.

A hotel room with a desk, chair, sofa, ottoman, and a large window.

A reception desk with a sign reading "HOME 2 Suites by Hilton," a minibar, a refrigerator labeled "COLDER," and a snack shelf.

A modern lounge area with green upholstered chairs, a herringbone-patterned floor, and a large window providing natural light.

Home2 Suites By Hilton Winter Haven

Winter Haven

S$218

includes taxes & fees

1 Nov - 2 Nov

A swimming pool area with people playing with building blocks.

A row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.

A dining area with tables, chairs, and a colorful mural in the background.

A children's play area with a slide and climbing structures, a small lighthouse, and a building with a red and white striped roof.

LEGOLAND Beach Retreat

Winter Haven

S$293

includes taxes & fees

12 Oct - 13 Oct

A hotel room with two beds, a TV, a microwave, and a desk with a lamp.

A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.

A restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.

A conference room with tables set for an event, featuring pink and white tablecloths and chairs with pink sashes.

Howard Johnson by Wyndham Winter Haven FL

Winter Haven

S$110

includes taxes & fees

18 Oct - 19 Oct

A reception area with a wooden floor, seating arrangements, and a reception desk.

A compact hotel room with a kitchenette, a patterned sofa, and a lamp.

A motel with a sign reading "Rodeway Inn & Suites," a blue pickup truck parked in the lot, and a building with a blue roof.

A motel with a sign reading "Rodeway Inn" in front of a parking lot.

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Winter Haven

S$116

includes taxes & fees

13 Oct - 14 Oct

A pool with floating building blocks and a colorful building with balconies in the background.

A dining area with tables and chairs, a central cart with dishes, and large windows with a view of greenery.

Two LEGO figures in front of a colorful hotel building with a sign that reads "HOTEL".

A room with a stone wall, a fireplace, and a sign that reads "YE OLD ADULTS KEEP OUT!".

Legoland Florida Hotel

Winter Haven

S$386

includes taxes & fees

27 Oct - 28 Oct

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Family-friendly hotels with pools in Winter Haven

A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.

A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.

A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.

A modern hotel with a prominent entrance, multiple floors, and a parking lot.

Best Western Plus Winter Haven Inn & Suites

Winter Haven

S$187

includes taxes & fees

18 Oct - 19 Oct

A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".

A hotel lobby with a reception desk, seating area, and a bar.

A hotel room with two beds, a large mirror, a wooden floor, and a view of the outdoors.

A hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.

Hampton Inn Winter Haven

Winter Haven

S$169

includes taxes & fees

8 Nov - 9 Nov

An outdoor patio with a fire pit, wicker furniture, and a view of a lake.

A modern hotel lobby with a long reception desk, bar area, and seating arrangement.

A Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.

A modern reception area with wooden panel walls and two reception desks.

Courtyard by Marriott Winter Haven

Winter Haven

S$206

includes taxes & fees

18 Oct - 19 Oct

A hotel room with two beds, a desk, a television, and a door leading to another room.

A hotel room with a desk, chair, sofa, and a painting on the wall.

A swimming pool with a poolside area, including lounge chairs and umbrellas, adjacent to a building with multiple windows and a brick facade.

A hotel dining area with multiple tables and chairs, ceiling lights, and artwork on the walls.

Holiday Inn Winter Haven by IHG

Winter Haven

S$159

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

A modern hotel room with a kitchenette, a dining area, and a bed.

A spacious, modern living area with a herringbone wood floor, a dining area with a wooden table and chairs, and a kitchen in the background.

A modern kitchen with a dining area, a flat-screen TV, and a large window.

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

S$192

includes taxes & fees

18 Oct - 19 Oct

An outdoor seating area with sofas, chairs, and a fire pit.

A hotel room with a desk, chair, sofa, ottoman, and a large window.

A reception desk with a sign reading "HOME 2 Suites by Hilton," a minibar, a refrigerator labeled "COLDER," and a snack shelf.

A modern lounge area with green upholstered chairs, a herringbone-patterned floor, and a large window providing natural light.

Home2 Suites By Hilton Winter Haven

Winter Haven

S$218

includes taxes & fees

1 Nov - 2 Nov

A swimming pool area with people playing with building blocks.

A row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.

A dining area with tables, chairs, and a colorful mural in the background.

A children's play area with a slide and climbing structures, a small lighthouse, and a building with a red and white striped roof.

LEGOLAND Beach Retreat

Winter Haven

S$293

includes taxes & fees

12 Oct - 13 Oct

A hotel room with two beds, a TV, a microwave, and a desk with a lamp.

A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.

A restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.

A conference room with tables set for an event, featuring pink and white tablecloths and chairs with pink sashes.

Howard Johnson by Wyndham Winter Haven FL

Winter Haven

S$110

includes taxes & fees

18 Oct - 19 Oct

A reception area with a wooden floor, seating arrangements, and a reception desk.

A compact hotel room with a kitchenette, a patterned sofa, and a lamp.

A motel with a sign reading "Rodeway Inn & Suites," a blue pickup truck parked in the lot, and a building with a blue roof.

A motel with a sign reading "Rodeway Inn" in front of a parking lot.

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Winter Haven

S$116

includes taxes & fees

13 Oct - 14 Oct

A wedding ceremony on a beach with a thatched gazebo and guests seated on chairs.

A marina with boats docked, surrounded by palm trees and a building with a covered area.

A building with a large water feature in front, surrounded by palm trees and a fence.

A lakeside view with a dock and a small building, likely a cabin or a house, surrounded by trees.

Lake Roy Beach Inn

Winter Haven

S$119

includes taxes & fees

11 Nov - 12 Nov

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

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent

"Great breakfast, room was clean, bed comfy and pillow selection good. Great location for Disney"

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent

"Great location l, I thought bed were comfortable..clean room weird smell but not too bad like a mold but I think it's more AC being on hot outside room was clean but a few minor issues that I didn't bring up to staff was tiny wormsbbut harmless and nothing to scary. They were escaping the heat. Pool was cool the lobby was cool"

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent

"I’ve been staying at this property for the past 6 years and it’s always an amazing stay."

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent

"Amazing time. Highly recommend for the full vaca experience, but with all the amenities of an apartment."

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"We had a great stay and if we ever return to Florida we would stay here again. washer/dryer in the unit was very convenient. Kitchen had basic utensils, pan, bowls, plates, coffee maker, blender, toaster, refrigerator/freezer, stove, microwave, dishwasher. starter supply of detergent, dish soap, dishwasher tabs, coffee were given."

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent

"Great spot for our volleyball tournament"

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 Holiday Inn Winter Haven by IHG.

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.

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