Places to stay in Winter Haven, FL

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Winter Haven, FL place to stay
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577 Best places to stay in Winter Haven, FL

Best family friendly Winter Haven, FL lodging

Among the 577 accommodations in Winter Haven, FL, here are the 4 best for families

2-bedroom, 2-bath Unit Offers A Family-friendly Retreat Just Mins From Legoland. - Winter Haven, FL
10 17 reviews
Winter Haven, FL
01/12 – 28/02
SG$261/nighttotal: SG$23229 (89 )

2-bedroom, 2-bath Unit Offers A Family-friendly Retreat Just Mins From Legoland.

2 2
apartment , Winter Haven
This two-bedroom, two-bathroom apartment in a gated Winter Haven community is located minutes (approximately 1.6km) from LEGOLAND Florida.
The 119 square metre ground-floor property sleeps six, boasts a fully equipped kitchen, in-unit laundry, smart TVs, and access to a heated pool, fitness centre, tennis court, and children's playground within the complex.
Lovely Home In Southern Dunes Golf & Country Club Gated Community - Winter Haven, FL
9.5 50 reviews
Winter Haven, FL
03/08 – 12/08
SG$235/nighttotal: SG$2115 (9 )

Lovely Home In Southern Dunes Golf & Country Club Gated Community

4 3
house , Haines City
This four-bedroom house is situated in the Southern Dunes Golf & Country Club gated community in Haines City, just 14 kilometres from Swanns Railroad Station (Historical) and 24 kilometres from Legoland Florida. The property has consistently received excellent ratings for location, cleanliness and overall user experience.
The 158 square metre dwelling comfortably accommodates up to ten guests and features a fully equipped kitchen, a private pool, a fitness centre, and a relaxing garden. Guests can also enjoy access to a golf course, an on-site restaurant, and outdoor play equipment for children.
The Poolside Escape - Winter Haven, FL
8.3 4 reviews
Winter Haven, FL
10/07 – 11/07
SG$490/nightfor 1 night

The Poolside Escape

1 4
house , Cypress Gardens
This Winter Haven residence is situated 4.3 kilometres from Legoland Florida and 15 kilometres from Swanns Railroad Station, offering convenient access to local attractions.
This detached house boasts a private swimming pool and spa, accommodates up to 15 guests with pets allowed for an additional charge, and includes a fully equipped kitchen, free WiFi, and air conditioning, covering a floor area of 6 square metres.
*Modern Tiny Lake Cottage*aceloc*4miles*legoland* - Winter Haven, FL
9.0 42 reviews
Winter Haven, FL
01/12 – 28/02
SG$100/nighttotal: SG$8900 (89 )

*Modern Tiny Lake Cottage*aceloc*4miles*legoland*

2 2
cottage , Winter Haven
This lakefront cottage is situated just three miles from Rotary Park, Baytree Golf Club, and Winter Haven Hospital, offering a peaceful retreat close to local attractions. The property has received excellent reviews from previous guests, highlighting its comfortable and convenient location.
The cottage has two bedrooms and one bathroom, accommodating up to three guests. It offers a fully equipped kitchen, a terrace, and access to the lake, perfect for enjoying the beautiful surroundings and local activities.

Best Winter Haven, FL accommodations with a kitchen

Modern 3br Home - Winter Haven, FL
9.8 81 reviews
Winter Haven, FL
10/07 – 11/07
SG$554/nightfor 1 night

Modern 3br Home

1 4
apartment , Cypress Gardens
This newly renovated house is located in Winter Haven, Florida, just 15 minutes from Legoland, 70 kilometers from Disney World, and around 90 kilometers from Busch Gardens, Sea World, and Universal Studios. The property has received excellent ratings for location, cleanliness, and overall user experience.
The three-bedroom, two-bathroom house can comfortably accommodate up to eight guests. It includes amenities like a fully equipped kitchen, a jacuzzi, a garden, and parking, making it a perfect choice for families or groups visiting Cypress Gardens.
2 King Beds + Fireplace + Fenced Yard Retreat - Winter Haven, FL
9.8 46 reviews
Winter Haven, FL
20/06 – 27/06
SG$219/nighttotal: SG$1533 (7 )

2 King Beds + Fireplace + Fenced Yard Retreat

1 2
house , Winter Haven
This Winter Haven cottage is conveniently located near Winter Haven Hospital (approx. 8km), AdventHealth Fieldhouse (approx. 11km), and the Diamondplex (approx. 14km), offering easy access to major attractions such as Legoland Florida (approx. 24km), Bok Tower Gardens (approx. 56km), and Walt Disney World Resort (approx. 72km).
The two-bedroom, one-bathroom property sleeps five, features a fully equipped kitchen with dishwasher, a washer/dryer, king-size beds, a fenced backyard, and complimentary Wi-Fi; enjoying a tranquil neighbourhood setting whilst being close to amenities.
4 Beds Near Legoland-adventhealth Fieldhouse - Winter Haven, FL
8.8 5 reviews
Winter Haven, FL
10/07 – 11/07
SG$404/nightfor 1 night

4 Beds Near Legoland-adventhealth Fieldhouse

3 4
apartment , Winter Haven
This one-bedroom suite is situated conveniently close to Legoland, offering easy access to the popular theme park for families visiting Winter Haven.
This flat provides a private kitchenette, air conditioning, parking, and accommodates up to two guests, making it a practical choice for those seeking a comfortable base for exploring local attractions and enjoying a restful stay.
Cheerful 4 Bed, 3 Bath Home With Screened Pool - Winter Haven, FL
10 139 reviews
Winter Haven, FL
25/06 – 29/06
SG$398/nighttotal: SG$1592 (4 )

Cheerful 4 Bed, 3 Bath Home With Screened Pool

1 5
apartment , Winter Haven
This stylish house is located in Winter Haven, just 10 kilometres from Legoland Florida, in a quiet family neighbourhood. It has received excellent ratings for its location, cleanliness, and overall experience.
The house has four bedrooms and three bathrooms, sleeping up to 11 guests. It has a fully equipped kitchen, a swimming pool, a private garden, and plenty of parking space, making it ideal for families or groups looking for a comfortable and convenient stay.

Frequently asked questions about accommodations in Winter Haven, FL

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Best Winter Haven, FL lodgings with a pool

Among the 577 accommodations in Winter Haven, FL, here are the 4 best ones with a pool

Beautiful Lake Front Cottage W/ Heated Pool & Hot Tub, 23 Miles From Disney - Winter Haven, FL
10 32 reviews
Winter Haven, FL
25/06 – 29/06
SG$545/nighttotal: SG$2180 (4 )

Beautiful Lake Front Cottage W/ Heated Pool & Hot Tub, 23 Miles From Disney

4 5
apartment , Winter Haven
This waterfront holiday home is located in Winter Haven, just a short drive from Legoland, Disney World, and Universal Studios, making it an ideal base for exploring Central Florida. The property has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
This spacious four-bedroom, three-bathroom property can accommodate up to ten guests, offering a comfortable and relaxing stay. The home features a private pool and hot tub, a fully equipped kitchen, a laundry room, and a terrace with stunning lake views, ensuring a memorable stay for families or groups of friends.
Heated Pool, Arcade With Ps5, 5min From Legoland-stylish Lakehome - Winter Haven, FL
10 11 reviews
Winter Haven, FL
01/12 – 28/02
SG$468/nighttotal: SG$41652 (89 )

Heated Pool, Arcade With Ps5, 5min From Legoland-stylish Lakehome

3 2
apartment , Cypress Gardens
This five-bedroom, three-bathroom holiday home in Winter Haven enjoys a lakeside setting, less than 5km from Baytree Golf Club and LEGOLAND Florida.
The property boasts a private pool, a fully equipped kitchen including a fridge, microwave, and dishwasher, free Wi-Fi, and accommodates up to six guests, with family-friendly amenities such as an arcade/game room.
3/2 House Near Legoland W Optional Heated Pool - Winter Haven, FL
9.9 104 reviews
Winter Haven, FL
03/08 – 12/08
SG$250/nighttotal: SG$2250 (9 )

3/2 House Near Legoland W Optional Heated Pool

1 3
apartment , Cypress Gardens
This three-bedroom apartment is situated just 5 kilometres from Legoland and the Peppa Pig theme park in Winter Haven, offering easy access to Cypress Gardens and other attractions. The apartment has excellent user, location, and cleanliness ratings, making it a great choice for families.
The self-catering accommodation comfortably sleeps up to 10 guests and features a fully equipped kitchen, a private pool, and a spacious backyard. Enjoy the heated pool, the Lego-themed kids' room, and the peaceful lake views from the front porch.
Winter Haven Guest House, 20 Min. To Legoland - Winter Haven, FL
9.7 41 reviews
Winter Haven, FL
20/06 – 27/06
SG$133/nighttotal: SG$931 (7 )

Winter Haven Guest House, 20 Min. To Legoland

1 2
house , Winter Haven
This B&B in Winter Haven offers a private 750 sq ft living space with a full kitchen and bathroom, including a walk-in shower, located in a quiet, safe neighbourhood just 5 minutes from downtown Winter Haven and 20 minutes from Legoland, with Tampa and Orlando approximately 160 kilometres away. Guests can enjoy a lakefront dock on Lake Howard, a game den with a pool table, shared outdoor spaces with a 75-inch TV and fire pit, and help-yourself food and beverages, with accommodation for up to two people featuring a king bed, futon, and queen air mattress.

Best Winter Haven, FL accommodations with parking

Kid-friendly Home W/ Pool & Bbq - Winter Haven, FL
10 111 reviews
Winter Haven, FL
10/07 – 11/07
SG$458/nightfor 1 night

Kid-friendly Home W/ Pool & Bbq

1 4
apartment , Winter Haven
This renovated three-bedroom house in Winter Haven, Florida, is situated approximately 32km from LEGOLAND Florida and 80km from Walt Disney World Resort.
The self-catering property sleeps seven guests and boasts a private pool, fully equipped kitchen, large patio with BBQ, and is baby-proofed; nearby, explore Winter Haven's chain of lakes.
Historic Love, Modern Appeal C - Winter Haven, FL
10 3 reviews
Winter Haven, FL
20/06 – 27/06
SG$145/nighttotal: SG$1015 (7 )

Historic Love, Modern Appeal C

1 2
apartment , Haines City
This studio apartment is located on the second floor of a repurposed doctor's office in Haines City, just 10km from LEGOLAND® Florida and Indigo's Family Fun Center, offering a quiet and unique stay with a touch of history. The apartment provides a comfortable and modern feel with stylish decor, perfect for a couple seeking a peaceful retreat.
The accommodation has a private balcony overlooking tall trees, ideal for enjoying a relaxing moment. Guests can also enjoy the convenience of a fully equipped kitchen with a fridge and microwave oven, as well as air conditioning and free Wi-Fi.
Hook, Line & Leisure: Lakefront Gem W/ Porch! - Winter Haven, FL
9.3 58 reviews
Winter Haven, FL
25/06 – 29/06
SG$307/nighttotal: SG$1228 (4 )

Hook, Line & Leisure: Lakefront Gem W/ Porch!

3 5
house , Winter Haven
This lakefront property is situated in Winter Haven, just a short drive from Legoland Florida and close to Swanns Railroad Station, offering a peaceful retreat away from the city centre. The house has received excellent ratings for cleanliness and user experience, with a good location rating.
The three-bedroom house, spanning 221 square metres, comfortably accommodates up to eight guests. Enjoy stunning lake views from the patio, prepare meals in the fully equipped kitchen, and stay connected with free Wi-Fi and cable TV.
Beautiful 3 Bedroom Pool Villa In Southern Dunes - Winter Haven, FL
9.4 3 reviews
Winter Haven, FL
25/06 – 29/06
SG$287/nighttotal: SG$1148 (4 )

Beautiful 3 Bedroom Pool Villa In Southern Dunes

3 5
apartment , Haines City
This Haines City holiday home is situated within a 15-minute walk of Southern Dunes Golf Club and Country Club, and within 9.6 kilometres of both the regional medical centre and Ember Dog Park.
This three-bedroom, three-bathroom property boasts 139 square metres of living space, comfortably accommodating six guests and featuring a private pool, fully equipped kitchen, and in-house laundry facilities.
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