Apartments and Condos in Winter Haven, FL

515 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Winter Haven, FL apartments
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

515 Apartments or condos in Winter Haven, FL

Best family friendly Winter Haven, FL apartment rentals

Among the 515 accommodations in Winter Haven, FL, here are the 4 best family friendly apartments

Cozy 1br Just 2 Miles From Legoland - Winter Haven, FL
10 1 review

Cozy 1br Just 2 Miles From Legoland

apartment, Cypress Gardens
This Winter Haven flat is located 2.9 kilometres from LEGOLAND Florida and 10.9 kilometres from Swanns Railroad Station.
This 93 square metre apartment, suitable for up to 7 guests, offers free Wi-Fi, air conditioning, a fully equipped kitchen, and a terrace, with complimentary private parking and car rental available on-site.
The Old Haven - An Enduring Piece Of Nostalgia - Winter Haven, FL
9.8 308 reviews

The Old Haven - An Enduring Piece Of Nostalgia

apartment, Winter Haven
This charming apartment is located in downtown Winter Haven, just a short walk from the lakes and the town's bustling centre. The property consistently receives excellent ratings for its location, cleanliness and user experience.
The apartment has four bedrooms and two bathrooms, comfortably accommodating up to nine guests. It is fully equipped with modern amenities and includes a garden, fitness centre, parking and a fully equipped kitchen.
Lake View, Game Room, 10 Min Legoland - Winter Haven, FL
10 124 reviews

Lake View, Game Room, 10 Min Legoland

apartment, Winter Haven
This fully renovated 1940s lake house is situated just a short drive from Winter Haven's charming downtown area, with its restaurants and shops, and within 10 minutes of Legoland. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious home can comfortably accommodate up to 10 guests in its four bedrooms and four bathrooms. The apartment offers a range of amenities for a comfortable stay, including a large kitchen, a dedicated games room, a swimming pool, and a spa.
Modern 3br/2ba - Private Pool - Near Legoland - Winter Haven, FL
9.8 74 reviews

Modern 3br/2ba - Private Pool - Near Legoland

apartment, Winter Haven
This three-bedroom house is situated in Winter Haven, Florida, just a short drive from Legoland and Disney, and within walking distance of the charming downtown area. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The house comfortably accommodates up to eight guests and features two bathrooms, a fully equipped kitchen, and a private pool. Guests can enjoy the relaxing beach theme decor, access to a washer and dryer, and the convenience of parking on-site.

Best Winter Haven, FL apartment rentals with a balcony

Getaway Clubhouse 5 Mil Legoland & .5 Mil Downtown - Winter Haven, FL
9.8 12 reviews

Getaway Clubhouse 5 Mil Legoland & .5 Mil Downtown

apartment, Winter Haven
This Winter Haven holiday home is conveniently located within 1.6 kilometres of Winter Haven Women's Hospital, Indigo's Family Fun Centre, Indigo's Billiards, Bowling & Games, Rotary Park, and Winter Haven Hospital, offering easy access to local amenities and attractions.
This spacious 150 square metre property boasts three bedrooms, three bathrooms, and can comfortably accommodate eight guests, featuring a fully equipped kitchen, laundry facilities, a garden, and terrace; ideal for families seeking self-catering accommodation near Winter Haven's leisure options.
Heated Pool, Arcade With Ps5, 5min From Legoland-stylish Lakehome - Winter Haven, FL
9.8 14 reviews

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

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.
Winter Haven Apt: 1 Mi To Polk State College! - Winter Haven, FL
10 18 reviews

Winter Haven Apt: 1 Mi To Polk State College!

apartment, Winter Haven
This Winter Haven apartment is conveniently located less than 1.6km from Rotary Park and Winter Haven Hospital, and under 4.8km from Winter Haven Women's Hospital and Indigo's Family Fun Center.
This 50 square metre, two-bedroom flat sleeps two guests and boasts a furnished kitchen, private balcony, free Wi-Fi, on-site parking, and a shared playground.
Family Friendly Lake House W/ Pool Near Legoland - Winter Haven, FL
10 8 reviews

Family Friendly Lake House W/ Pool Near Legoland

apartment, Winter Haven
This five-bedroom, four-bathroom holiday home in Winter Haven, Florida, is located a 3-minute drive from Indigo's Family Fun Centre and a 5-minute drive from Chain of Lakes Park.
The 304 square metre property boasts a heated swimming pool, garden, terrace, and ample amenities including kayaks, a games room, and free Wi-Fi, comfortably accommodating up to twelve guests.

Frequently Asked Questions about apartment rentals in Winter Haven, FL

  • What are the top cultural and historical sites in Winter Haven, FL?

    The Winter Haven Historical Society Museum is a must-visit for history buffs. It's housed in the old Winter Haven City Hall and has a great collection of local artifacts. For a bit of art and culture, the Polk Museum of Art is a great place to spend an afternoon. It has a diverse collection of works and hosts a variety of exhibitions throughout the year.
  • What are the best apartments in Winter Haven, FL?

    Among the apartments in Winter Haven, FL, Horse Farm On A Beautiful Lake, 2 Bedroom Apartment and Ariana Place - Tree House Like Lakefront Views are the most popular ones.

  • What makes Winter Haven, FL unique or famous?

    Winter Haven is known as the 'Chain of Lakes City' because it has over 500 lakes. It's a popular destination for water sports, especially boating and fishing. It's also home to Legoland Florida, which is a huge attraction for families.
  • What are the best apartments with a pool in Winter Haven, FL?

  • Where can you find the best local markets and street food in Winter Haven, FL?

    Winter Haven has a few great markets, but for local food, you can't beat the Winter Haven Farmers Market. It's held every Saturday morning at the Central Park and has a great selection of local produce, baked goods, and crafts. For a more casual experience, there are a few food trucks that set up shop around the city, especially on weekends.
  • What are the best apartments with a jacuzzi in Winter Haven, FL?

  • How is the public transportation system in Winter Haven, FL?

    Winter Haven has a public bus system called Winter Haven Transit. It's not as extensive as in larger cities, but it's a good option for getting around the city centre and to some of the surrounding areas. You can find bus schedules and routes on the Winter Haven Transit website.
  • What are the best apartments for families and kids in Winter Haven, FL?

    The best apartments for families and kids in Winter Haven, FL are Horse Farm On A Beautiful Lake, 2 Bedroom Apartment and Historic 1910 Pool Home Close To Legoland & Disney.

  • Which seasonal events or festivals should apartment renters look forward to in Winter Haven, FL?

    You should check out the Winter Haven Christmas Parade, it's a big deal here. There's also the Spring Fling Festival, which is a great way to enjoy the warmer weather. And for something a bit different, the Winter Haven Air Show is a real spectacle.
  • What are the best pet friendly apartments in Winter Haven, FL?

  • What amenities are typically included in apartments in Winter Haven, FL?

    Most apartments in Winter Haven will come with central air conditioning and heating. Many will also have a washer and dryer in the unit. Some will have a swimming pool and fitness centre, but those are usually found in larger complexes.
  • What are the best apartments with parking in Winter Haven, FL?

    Horse Farm On A Beautiful Lake, 2 Bedroom Apartment and Ariana Place - Tree House Like Lakefront Views are the best apartments with parking in Winter Haven, FL.

  • What leisure activities are available for relaxation in Winter Haven, FL?

    For relaxation, you can't beat spending a day by one of the many lakes. You can go for a swim, rent a boat, or just relax on the shore. There are also a few golf courses in the area, and the Winter Haven Public Library is a great place to escape the heat and relax with a good book.

Popular destinations

Best Winter Haven, FL apartment rentals with parking

Family Fun Haven: 3 Bed/2 Bath/6 Mi To Legoland/pet Friendly! - Winter Haven, FL
9.6 31 reviews

Family Fun Haven: 3 Bed/2 Bath/6 Mi To Legoland/pet Friendly!

apartment, Winter Haven
This three-bedroom home is located in Winter Haven, Florida, just 15 kilometres from LEGOLAND and Peppa Pig Theme Park, and within a 10-kilometre drive of shops, restaurants, and parks. The apartment is perfect for families, with a fully fenced garden and a capacity for up to eight guests.
The apartment is equipped with a modern kitchen, a 55-inch Smart TV with Netflix and Hulu, and a washer and dryer, as well as a keyless entry system for convenient check-in and check-out. Guests can also enjoy the fully fenced garden, perfect for relaxing or playing games.
Magnolia Farmhouse- Cozy With A Perfect Patio - Winter Haven, FL
9.7 56 reviews

Magnolia Farmhouse- Cozy With A Perfect Patio

apartment, Winter Haven
This renovated 1928 farmhouse, situated in a historic Winter Haven neighbourhood, is a 0.8km walk from a lake with a boat ramp and a 24km drive from LEGOLAND® Florida and Peppa Pig Theme Park.
This two-bedroom, two-bathroom property sleeps six guests and features a fully equipped kitchen, air conditioning, a garden, a fitness centre, parking, Roku TVs in each room, and family-friendly amenities including toys and games.
Waterfront Condo | Pool & Dock | Near Legoland | 2br, Sleeps 4 - Winter Haven, FL
10 8 reviews

Waterfront Condo | Pool & Dock | Near Legoland | 2br, Sleeps 4

apartment, Winter Haven
This Winter Haven holiday apartment is conveniently located near Chain of Lakes Park (approx. 6.4 km) and LEGOLAND® Florida (approx. 8 km).
The 78 square metre property offers two bedrooms, two bathrooms, sleeps four, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, and a balcony; enjoy watersports on the nearby waterfront.
3/2speciousmodern4miles-legoland - Winter Haven, FL
9.7 410 reviews

3/2speciousmodern4miles-legoland

apartment, Winter Haven
This lakeside holiday home in Winter Haven is conveniently located just two miles from the town centre and hospital, and within easy reach of LEGOLAND and Peppa Pig theme parks. The property enjoys an excellent user rating and is highly praised for its cleanliness and location.
The house spans 111 square metres and comfortably accommodates up to six guests with three bedrooms and two bathrooms. Guests can enjoy a range of amenities including a fully equipped kitchen, a private dock for boat access, and a secure parking space.

Best Winter Haven, FL apartment rentals with air conditioning

2-bedroom, 2-bath Unit Offers A Family-friendly Retreat Just Mins From Legoland. - Winter Haven, FL
10 21 reviews

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

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.
"Chalet" Lake House/walking Path/fenced Yard/dock - Winter Haven, FL
9.9 16 reviews

"Chalet" Lake House/walking Path/fenced Yard/dock

apartment, Winter Haven
This lakefront ski chalet in Winter Haven offers direct access to Lake Elbert via a private dock, situated just 1 kilometre from downtown Winter Haven and 1 kilometre from Winter Haven Hospital and Polk State College.
This two-bedroom, one-bathroom apartment sleeps up to six guests, featuring a fully equipped kitchen, a piano, and outdoor amenities including Adirondack chairs and a gas grill, with a 2-kilometre walking path around the lake and proximity to Legoland (4.8 kilometres) and the Chain O' Lakes Sports Complex (2.2 kilometres).
2 - Ships Ahoy Bungalow 2 Bed/2 Bath - Unit 17 - Winter Haven, FL
9.7 673 reviews

2 - Ships Ahoy Bungalow 2 Bed/2 Bath - Unit 17

apartment, Winter Haven
This charming cottage is located in Cypress Inlet Vacation Homes and Marina in Winter Haven, Florida, just a short drive from Legoland and other attractions. It has received excellent ratings for its cleanliness, location and overall experience.
This two-bedroom property offers a comfortable and stylish living space. Guests can enjoy direct canal access to Lake Eloise, a covered porch, a well-equipped kitchen, three Smart TVs, and a boat ramp on a private canal.
4 Bedroom, Legoland, Pet Friendly, Pool, Gameroom - Winter Haven, FL
9.4 80 reviews

4 Bedroom, Legoland, Pet Friendly, Pool, Gameroom

apartment, Winter Haven
This Winter Haven holiday home, sleeping up to 15 guests, offers excellent user ratings and is conveniently located near Legoland Florida, Bok Tower Gardens, and Cypress Gardens (exact distances unspecified).
The four-bedroom, two-bathroom property boasts a fully equipped kitchen including a dishwasher, air conditioning, a swimming pool, garden, parking, and internet access; further details on specific dimensions, layout, and on-site activities are unavailable.
©2026 cozycozy.com