Apartments and Condos in Winter Haven

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Winter Haven apartments
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515 Apartments or condos in Winter Haven

Browse Apartments in the Historic District of Winter Haven

Live like a local by choosing downtown apartments in Winter Haven, offering seamless walking access to top restaurants and shopping districts.

Downtown Winter Haven Retreat | Arcade + Fast Wifi - Winter Haven
10 2 reviews

Downtown Winter Haven Retreat | Arcade + Fast Wifi

apartment, Winter Haven
This downtown Winter Haven condo offers prime access to shops and dining, with local attractions just minutes away.
This pet-friendly, 3-bedroom unit accommodates up to 5 guests and features a full kitchen, air conditioning, WiFi, and an arcade machine for entertainment.
Cozy 1 Bedroom Home In Winter Haven Perfect For Your Getaway. - Winter Haven
10 4 reviews

Cozy 1 Bedroom Home In Winter Haven Perfect For Your Getaway.

apartment, Winter Haven
This 1-bedroom, 1-bathroom apartment in Winter Haven offers convenient access to downtown, located just 2 minutes away, and is within walking distance of Lake Howard. It is a short drive to Winter Haven Hospital, AdventHealth Fieldhouse, and Legoland Florida Resort, with Bok Tower Gardens and Grand Hotel also nearby.
This rental accommodates up to 3 guests and features a fully equipped kitchen, air conditioning, and a dedicated two-car parking space, with pets allowed and internet access provided.
The Old Haven - An Enduring Piece Of Nostalgia - Winter Haven
9.8 15 reviews

The Old Haven - An Enduring Piece Of Nostalgia

apartment, Winter Haven
This lakeside Winter Haven vacation home is situated near Indigo's Family Fun Center and Winter Haven Hospital, a short drive from Rotary Park and a 25-minute walk from Winter Haven Station.
This 1800-square-foot property boasts four bedrooms, two bathrooms, and accommodates up to nine guests, featuring a fully equipped kitchen, fitness center, terrace, and a tranquil lakeside setting ideal for water activities.
Cozy 1-bedroom Retreat Near Downtown & Legoland - Winter Haven
10 2 reviews

Cozy 1-bedroom Retreat Near Downtown & Legoland

apartment, Winter Haven
This Winter Haven apartment rental is minutes from downtown, LEGOLAND Florida, and a hospital, offering easy highway access and a 45-minute drive to Walt Disney World.
The one-bedroom, one-bathroom unit sleeps two guests and features a small kitchenette with a mini-fridge, microwave, and electric hot plate, plus convenient proximity to Indigo's Family Fun Center and Willowbrook Golf Course.

Best Winter Haven apartment rentals with air conditioning

3/2 Great Family Home Near Legoland - Winter Haven
9.8 178 reviews

3/2 Great Family Home Near Legoland

apartment, Winter Haven
This 3-bedroom apartment is centrally located in Winter Haven, just a short drive from Legoland and Winter Haven Hospital. The property has received excellent ratings for cleanliness, location, and overall experience.
The apartment comfortably accommodates up to 7 guests and features a spacious layout with an open kitchen, dining, and living area. Amenities include a fully equipped kitchen, air conditioning, a private garden, and parking.
Dundee | King Bed Non Smoking - Winter Haven
10 122 reviews

Dundee | King Bed Non Smoking

apartment, Dundee
This Dundee rental unit is situated on a lake, 6.2 miles from Legoland Florida and 42.9 miles from Orlando International Airport.
This 150-square-foot apartment accommodates two guests with one bedroom and one bathroom, offering air conditioning, complimentary WiFi, and access to a seasonal outdoor swimming pool, with motor boating and swimming opportunities nearby.
Pet Friendly Central Florida Bungalow - Winter Haven
9.9 47 reviews

Pet Friendly Central Florida Bungalow

apartment, Lake Alfred
This Lake Alfred bungalow, near Orlando, offers convenient access to major theme parks (under 1 hour to Disney World, Universal Studios, SeaWorld, and Busch Gardens), Florida's beaches (within 1.5 hours), and natural springs (under 2 hours).
This two-bedroom, one-bathroom house sleeps five, features a fully equipped kitchen with a fridge and microwave, air conditioning, parking, internet access, a fenced yard with a dog door, and includes Disney+ streaming—perfect for families and pet owners seeking a relaxing getaway near Orlando's attractions.
Spacious Home, In A Quiet Neighborhood Near Legoland®-just A 12-minute Drive - Winter Haven
9.4 11 reviews

Spacious Home, In A Quiet Neighborhood Near Legoland®-just A 12-minute Drive

apartment, Winter Haven
This vacation home in Winter Haven is conveniently located near Sertoma Park, Indigo's Billiards, Bowling & Games, and Theatre Winter Haven. It has received excellent user ratings, making it a top choice for travelers.
The house features 4 bedrooms and 2 bathrooms, accommodating up to 10 guests comfortably. It includes a fully equipped kitchen, air conditioning, a swimming pool, a terrace/balcony, a garden, parking, and free WiFi. Guests can also enjoy access to a water park, barbecue grills, and a fenced private yard.

Frequently Asked Questions about apartment rentals in Winter Haven

  • What are the must-see attractions for a 2 days stay in Winter Haven, FL?

    For a two-day trip, you'll want to check out Legoland Florida, a theme park with rides and shows for all ages. You can also spend some time at the Polk Museum of Art, which has a great collection of American and European art. If you're looking for something outdoorsy, head over to the Chain of Lakes Park, which has a large playground, a fishing pier, and a walking trail.
  • What are the best apartments in Winter Haven?

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

  • Which neighborhoods in Winter Haven, FL are best for renting an apartment?

    The best neighborhoods for renting an apartment in Winter Haven are Cypress Gardens, which is close to the theme parks and has many restaurants and shops, and the downtown area, which is a bit more historic and has a lot of character. You can also find some nice apartments in the area near the Chain of Lakes.
  • What are the best apartments with a pool in Winter Haven?

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

    Winter Haven has a rich history, and some of the best cultural and historical sites include the Winter Haven Historical Society Museum, which has exhibits on the city's past, and the Bok Tower Gardens, a beautiful botanical garden with a 205-foot-tall carillon tower.
  • What are the best apartments with a jacuzzi in Winter Haven?

  • What makes Winter Haven, FL unique or famous?

    Winter Haven is known as the 'Chain of Lakes City' because it has 14 interconnected lakes. It's also home to Legoland Florida, a popular theme park, and Cypress Gardens, a beautiful botanical garden. If you're looking for a relaxing vacation with some fun attractions, Winter Haven is a great choice.
  • What are the best apartments for families and kids in Winter Haven?

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

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

    Winter Haven has a few local markets, like the Winter Haven Farmers Market, which takes place every Saturday morning at the downtown Central Park. You can find fresh produce, baked goods, and local crafts there. There are also some great food trucks in the area, especially near the theme parks.
  • What are the best pet friendly apartments in Winter Haven?

  • 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 some larger cities, but it can get you around the main areas of town. If you're planning on visiting the theme parks or other attractions outside of the city center, you'll probably want to rent a car.
  • What are the best apartments with parking in Winter Haven?

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

    Winter Haven hosts several fun events throughout the year. The biggest one is the annual Winter Haven Christmas Parade, which takes place in December. There's also the Chain of Lakes Festival in April, which celebrates the city's lakes with live music, food, and activities.
  • What amenities are typically included in apartments in Winter Haven, FL?

    Most apartments in Winter Haven include basic amenities like a refrigerator, stove, and oven. Some apartments also have central air conditioning, a washer and dryer, and a balcony or patio. You can find apartments with different amenities depending on your budget and needs.
  • What leisure activities are available for relaxation in Winter Haven, FL?

    Winter Haven is a great place to relax and enjoy the outdoors. You can go for a swim, kayak, or paddleboard in one of the lakes. You can also go for a walk or bike ride on the many trails in the area. If you're looking for something a little more active, there are several golf courses and tennis courts in Winter Haven.

Popular destinations

Search Apartments with Balconies in Winter Haven

Morning coffee with views of the skyline is a simple pleasure when staying in these vacation apartments of Winter Haven.

Heated Pool, Arcade With Ps5, 5min From Legoland-stylish Lakehome - Winter Haven
9.8 14 reviews

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

apartment, Cypress Gardens
This five-bedroom, three-bathroom Winter Haven vacation home is located near Cypress Gardens, within three miles of Baytree Golf Club and LEGOLAND Florida.
The property boasts a private pool, a terrace, a fully equipped kitchen including a refrigerator, microwave, and dishwasher, free WiFi, and accommodates up to six guests, perfect for families visiting the area's attractions.
78 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Winter Haven
No reviews

78 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

apartment, Winter Haven
This 2-bedroom, 2-bathroom condo rental in Winter Haven, Florida, offers direct Lake Lulu access and is located 3 miles from LEGOLAND Florida Resort and 3.7 miles from Peppa Pig Theme Park.
The 840-square-foot unit features a fully equipped kitchen, screened patio with lake views, in-unit laundry, and accommodates up to 4 guests, with access to a community pool and dock.
Family & Sports Team Oasis Near Legoland & Parks - Winter Haven
No reviews

Family & Sports Team Oasis Near Legoland & Parks

apartment, Winter Haven
This 6-bedroom, 3-bathroom vacation home in Winter Haven offers convenient access to Indigo's Family Fun Center and Theatre Winter Haven, both just a 5-minute drive away, as well as Circle B Bar Reserve and Lake Cannon.
This spacious rental accommodates up to 16 guests with amenities including a full kitchen, air conditioning, Wi-Fi, a garden with outdoor furniture, a private terrace, and on-site parking.
Family Friendly Lake House W/ Pool Near Legoland - Winter Haven
10 8 reviews

Family Friendly Lake House W/ Pool Near Legoland

apartment, Winter Haven
This spacious Winter Haven lakefront home boasts a prime location on Lake Otis, just 10 minutes from LEGOLAND® Florida.
The 3,580-square-foot property features five bedrooms, four bathrooms, sleeps up to 12 guests, and includes a saltwater pool, game room, and expansive covered patio with a Blackstone grill—perfect for family vacations or group getaways.

Check Out Family Apartments in Winter Haven

Choosing a vacation apartment built for families in Winter Haven ensures city attractions are within easy reach, making for a stress-free stay.

Newly Vacation Home With Lake View - Winter Haven
9.9 43 reviews

Newly Vacation Home With Lake View

apartment, Lake Alfred
This Lake Alfred vacation home sits just 1.5 miles from Lions Park and within 6 miles of several other attractions, making it a convenient base for exploring the area. The property has received excellent ratings for location, cleanliness, and overall experience.
The 3-bedroom house comfortably sleeps 6 guests and offers 1600 square feet of living space. Amenities include a fully equipped kitchen, a private yard, a terrace or balcony, air conditioning, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Arcade+pingpong + 10 Guests + 11 Mil To Lego Land! - Winter Haven
9.9 91 reviews

Arcade+pingpong + 10 Guests + 11 Mil To Lego Land!

apartment, Winter Haven
This spacious Winter Haven home, perfect for families or large groups, is conveniently located 11 miles from Legoland Florida Resort, 27 miles from Walt Disney World, and 34 miles from Universal Studios Florida.
The 4-bedroom, 2-bathroom house sleeps up to 10 guests and features a large backyard, full kitchen with dishwasher, air conditioning, and free parking; professional pest control ensures a comfortable stay.
Getaway Clubhouse - 5 Mi Legoland & 0.5 Mi Dtwn - Winter Haven
9.9 53 reviews

Getaway Clubhouse - 5 Mi Legoland & 0.5 Mi Dtwn

apartment, Winter Haven
This family-friendly vacation rental in Winter Haven is conveniently located near Legoland Florida, a 15-minute drive away, and the Polk Museum of Art, a 10-minute drive away. The 3-bedroom, 2-bathroom home sleeps up to 8 guests and includes a fully equipped kitchen, a relaxing garden, and entertainment options like board games and foosball.
Large Family Home, Legoland, Pet Friendly, 7 Beds - Winter Haven
10 25 reviews

Large Family Home, Legoland, Pet Friendly, 7 Beds

apartment, Winter Haven
This lakefront Winter Haven home, located within three miles of Sertoma Park, Indigo's Billiards, Bowling & Games, Indigo's Family Fun Center, and Winter Haven Hospital, offers convenient access to family-friendly entertainment and healthcare.
This 2,680-square-foot vacation rental boasts four bedrooms, two bathrooms, sleeps twelve guests, and includes a private patio, swimming pool, spa, and free Wi-Fi.

Guest-Favorite Apartments with Parking in Winter Haven

On-site parking takes one thing off your list when visiting Winter Haven, as every vacation apartment here has it included.

Legoretreat- Game Room/legoland/peppa Pig/dinning - Winter Haven
No reviews

Legoretreat- Game Room/legoland/peppa Pig/dinning

apartment, Eagle Lake
Private Pool Lake House With Game Roomjust 4 Minutes From Legoland - Winter Haven
10 83 reviews

Private Pool Lake House With Game Roomjust 4 Minutes From Legoland

apartment, Winter Haven
Escape To Tranquility At This Privatepool Lakeview Getaway On The Shores Of El - Winter Haven
9.2 5 reviews

Escape To Tranquility At This Privatepool Lakeview Getaway On The Shores Of El

apartment, Eagle Lake
Mid-century Modern Home Near Downtown Winter Haven - Winter Haven
10 1 review

Mid-century Modern Home Near Downtown Winter Haven

apartment, Winter Haven

Browse 5-Star Vacation Apartments in Winter Haven

There is a lot to be said for a well-chosen luxury vacation apartment in Winter Haven that offers the space of a home with the finishes of a hotel.

Sweet Cottage - 5 Mi To Legoland & 0.5 Mi To Dtwn - Winter Haven
9.6 235 reviews

Sweet Cottage - 5 Mi To Legoland & 0.5 Mi To Dtwn

apartment, Winter Haven

Explore Pet-Friendly Apartments in Winter Haven

Bringing your dog to Winter Haven? Every vacation apartment on this list features nearby dog parks and convenient city walks.

Spacious Lakefront 5br Home, Near Disney, Legoland - Winter Haven
No reviews

Spacious Lakefront 5br Home, Near Disney, Legoland

apartment, Lake Hamilton
Private King Suite With W/d Near Legoland & Winter Haven Hospital - Winter Haven
8.4 9 reviews

Private King Suite With W/d Near Legoland & Winter Haven Hospital

apartment, Winter Haven
Us_dnf001_2 Full Bed - Winter Haven
9.6 37 reviews

Us_dnf001_2 Full Bed

apartment, Dundee
Winter Haven 1 Br 1 Ba Condo 7 On Chain Of Lakes - Winter Haven
8.0 4 reviews

Winter Haven 1 Br 1 Ba Condo 7 On Chain Of Lakes

apartment, Winter Haven

Top-Rated Apartments with a Pool in Winter Haven

On-site pool access in Winter Haven makes a proper swim in the heart of the city a wonderful part of your daily routine.

Us_dnf001_2 Queen Bed - Winter Haven
9.6 32 reviews

Us_dnf001_2 Queen Bed

apartment, Dundee
Lake Alfred Pool Home! Summer Fun, Nature Lovers - Winter Haven
9.4 7 reviews

Lake Alfred Pool Home! Summer Fun, Nature Lovers

apartment, Lake Alfred
6 Mi To Legoland: Retreat W/ Pool & Fenced Yard - Winter Haven
9.6 27 reviews

6 Mi To Legoland: Retreat W/ Pool & Fenced Yard

apartment, Winter Haven
Winter Haven Waterfront Retreat - Winter Haven
10 41 reviews

Winter Haven Waterfront Retreat

apartment, Cypress Gardens

Our Favorite Apartments with a Hot Tub in Winter Haven

Whether you prefer a jacuzzi or a hot tub, these vacation apartments of Winter Haven include one for a private soak at the end of the day.

1/1 Condo Located On Lk Lulu. 7 Minutes From Legoland. Access To Hwy 27, 17 & I4 - Winter Haven
No reviews

1/1 Condo Located On Lk Lulu. 7 Minutes From Legoland. Access To Hwy 27, 17 & I4

apartment, Winter Haven
Private Lakefront Retreat - Winter Haven
10 13 reviews

Private Lakefront Retreat

apartment, Winter Haven
Sunset Lakefront Home | Hot Tub, Private Dock - Winter Haven
10 2 reviews

Sunset Lakefront Home | Hot Tub, Private Dock

apartment, Eagle Lake
Adult-only Retreat W/ Pool & Spa | 18+, Private - Winter Haven
10 133 reviews

Adult-only Retreat W/ Pool & Spa | 18+, Private

apartment, Cypress Gardens
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