Holiday Rentals in Winter Haven, FL

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Winter Haven, FL holiday rentals
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684 Holiday rentals and Airbnb in Winter Haven, FL

Best family friendly Winter Haven, FL holiday rentals

Among the 684 accommodations in Winter Haven, FL, here are the 4 best family friendly rentals

Legoland Splash Escape With Pool And Hot Tub! - Winter Haven, FL
10 70 reviews

Legoland Splash Escape With Pool And Hot Tub!

apartment, Winter Haven
This four-bedroom apartment in Winter Haven, Florida, is just a short drive from Cypress Gardens and LEGOLAND® Florida. It has received excellent reviews from previous guests.
The property can accommodate up to eight guests and includes a dedicated LEGO bedroom for children. It boasts a private pool and hot tub, a game room with a pool table and air hockey, and an optional heated pool for year-round enjoyment.
Pet Friendly Central Florida Bungalow - Winter Haven, FL
9.9 47 reviews

Pet Friendly Central Florida Bungalow

apartment, Lake Alfred
This Lake Alfred bungalow, near Orlando, offers convenient access to Disney World (under 80km), Universal Studios (under 80km), SeaWorld (under 80km), and Busch Gardens (under 80km), plus Florida's east and west coasts within 240km.
The two-bedroom, one-bathroom property sleeps five, features a fully equipped kitchen including a fridge and microwave, air conditioning, parking, internet access, Disney+ streaming, a fenced yard with a pet door, and queen-sized beds in each bedroom.
Newly Vacation Home With Lake View In Lake Alfred - Winter Haven, FL
9.9 43 reviews

Newly Vacation Home With Lake View In Lake Alfred

apartment, Lake Alfred
This charming lakefront house is situated just 2.4 kilometres from Lions Park, offering a peaceful retreat close to local attractions. The property benefits from excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The 149 square metre house comfortably accommodates up to six guests across its three bedrooms and two bathrooms. Guests can enjoy stunning lake views, direct water access, a private yard, a fully equipped kitchen, free Wi-Fi, air conditioning, and a terrace or balcony.
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.

Best Winter Haven, FL holiday rentals with parking

Lake Lulu Escape - Winter Haven, FL
No reviews

Lake Lulu Escape

house, Winter Haven
Lake Lulu Escape, a holiday home in Winter Haven, is conveniently located 4.7 kilometres from Legoland Florida and within a 26-kilometre radius of several historical railway stations.
This detached property offers accommodation for up to seven guests, featuring air conditioning, a fully equipped kitchen with a dishwasher, and a dedicated seating area, with Lakeland Linder International Airport 33.8 kilometres away.
Lakefront Home On The Winter Haven Chain Olakes! - Winter Haven, FL
9.9 116 reviews

Lakefront Home On The Winter Haven Chain Olakes!

apartment, Cypress Gardens
This apartment is located on the beautiful Lake Roy, just a short distance from Cypress Gardens, offering easy access to the attractions and the scenic Winter Haven Chain O’Lakes. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The apartment features a spacious living area, a fully equipped kitchen, and a dining area, comfortably accommodating up to 5 guests. Enjoy a range of amenities including direct lake access for swimming, fishing, and boating, boat rentals, water sports facilities, a private keyless entry, outdoor shower and tub, free parking, and a pool table.
Romantic Historic Private Apartment Studio - Winter Haven, FL
9.9 16 reviews

Romantic Historic Private Apartment Studio

house, Winter Haven
This studio apartment is situated in a tranquil Winter Haven neighbourhood, a short drive from restaurants, hospitals, universities, and Legoland.
This private, one-bedroom dwelling for two guests offers a kitchenette, air conditioning, and access to a shared garden with a barbecue area, alongside a designated parking space.
Luxury By Legoland 104 - Winter Haven, FL
10 42 reviews

Luxury By Legoland 104

apartment, Winter Haven
This ground-floor apartment in a new luxury complex is located less than 1.6 kilometres from LEGOLAND Florida Resort, near Winter Haven's Chain of Lakes.
The two-bedroom, two-bathroom flat sleeps six guests and boasts a LEGOLAND-themed children's bedroom, a fully equipped kitchen, in-unit laundry, and access to a resort-style pool, fitness centre, and fire pits.

Frequently asked questions about holiday rentals in Winter Haven, FL

  • What are the top family-friendly attractions in Winter Haven, FL?

    For families, Legoland Florida is a top choice. You can also visit the Polk Museum of Art, which has a dedicated children's gallery, and the Winter Haven Public Library, which hosts regular events for kids. For a day outdoors, head to the Chain of Lakes for a picnic or a boat ride.
  • What are the best Airbnb and holiday rentals in Winter Haven, FL?

    *3\/2*gorgeousnewlakehome2aceloc*4mi*legoland*1724, 2 Bedroom Apartment and The Russell Lake House are among the best Airbnb and holiday rentals in Winter Haven, FL.

  • When is the best time to book a vacation rental in Winter Haven, FL?

    The best time to book a vacation rental in Winter Haven is during the shoulder seasons, from April to May and September to October. The weather is still pleasant, and you'll find fewer crowds and more affordable prices compared to peak season.
  • What are the most popular Airbnbs in Winter Haven, FL?

  • What events or festivals should visitors check out in and around Winter Haven, FL?

    Winter Haven hosts several events throughout the year, including the annual Winter Haven Art Festival, which showcases local artists and craftspeople. You can also check out the Cypress Gardens Festival of Lights during the holiday season. If you're looking for something a bit further afield, the Sun 'n Fun International Fly-In & Expo in Lakeland is a major event for aviation enthusiasts.
  • What are the best holiday rentals with a pool in Winter Haven, FL?

    2 Bedroom Apartment, The Russell Lake House and Perfect For Large Family 5 Bedroom are the best holiday rentals with a pool in Winter Haven, FL.

  • What are the best budget-friendly activities in Winter Haven, FL?

    Winter Haven offers plenty of budget-friendly activities. You can enjoy a walk or bike ride along the Chain of Lakes, visit the Winter Haven Public Library, or explore the historic downtown area. You can also pack a picnic and enjoy a day at one of the many parks, such as the Chain of Lakes Park or the Lake Alfred Public Beach.
  • What are the best rentals for families and kids in Winter Haven, FL?

    The best rentals for families and kids in Winter Haven, FL are *3\/2*gorgeousnewlakehome2aceloc*4mi*legoland*1724, 2 Bedroom Apartment and The Russell Lake House.

  • What are the best restaurants with local dishes in Winter Haven, FL?

    For local dishes, try The Terrace Restaurant at the Chain of Lakes, which serves classic Florida cuisine with a modern twist. For a more casual dining experience, head to The Boathouse Restaurant, which offers fresh seafood and waterfront views.
  • What are the best rentals or Airbnbs with a jacuzzi in Winter Haven, FL?

  • What are the best walking or cycling routes in Winter Haven, FL?

    The Chain of Lakes Trail is a popular walking and cycling route that winds its way through the city, offering scenic views of the lakes and parks. For a shorter route, try the Winter Haven Linear Park, which follows the CSX railroad line and features a variety of native plants and wildlife.
  • Are there pet-friendly attractions in Winter Haven, FL?

    Yes, many places in Winter Haven are pet-friendly. The Chain of Lakes Park has a designated dog park, and many restaurants and shops welcome furry friends. You can also find pet-friendly vacation rentals in the area.
  • What are the benefits of choosing a vacation rental in Winter Haven, FL?

    Vacation rentals offer more space and privacy compared to hotels, and you'll often find them to be more affordable, especially for families or groups. They also provide a more home-like experience, allowing you to cook your own meals and relax in a comfortable setting.
  • What are the top sports attractions and facilities in Winter Haven, FL?

    Winter Haven is home to the Chain of Lakes, which offers a variety of watersports, including boating, fishing, and swimming. You can also find golf courses, tennis courts, and other recreational facilities throughout the city.

Popular destinations

Best Winter Haven, FL holiday rentals with a balcony

Hook, Line & Leisure: Lakefront Gem W/ Porch! - Winter Haven, FL
9.3 60 reviews

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

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.
Lakefront Vacation Home On The Chain Of Lakes In Winter Haven - Winter Haven, FL
9.6 8 reviews

Lakefront Vacation Home On The Chain Of Lakes In Winter Haven

apartment, Winter Haven
This three-bedroom, two-bathroom houseboat on the Chain of Lakes in Winter Haven offers stunning sunrise views and is conveniently located near Winter Haven Municipal Airport and Brown's Seaplane Base, approximately 10-20 km from LEGOLAND Florida and further from Orlando's theme parks (exact distances vary).
The 5-guest vessel boasts a fully equipped kitchen, screened porch, smart TVs, Wi-Fi, air conditioning, and a private garden, perfect for watersports enthusiasts with easy access to numerous lakes via connected channels.
Golf, Dine & Unwind Poolside! Haines City Getaway - Winter Haven, FL
8.0 1 review

Golf, Dine & Unwind Poolside! Haines City Getaway

house, Haines City
This detached residence is situated in Haines City, 12.2 kilometres from Legoland Florida and 7.6 kilometres from Swanns Railroad Station.
This property offers 297 square metres of living space, accommodating up to 15 guests with 3 bedrooms and 4 bathrooms, featuring a swimming pool, air conditioning, Wi-Fi, and on-site parking.
6 Mi To Legoland: Retreat W/ Pool & Fenced Yard - Winter Haven, FL
10 2 reviews

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

house, Winter Haven
This Winter Haven holiday home is situated 4.9 km from Swanns Railroad Station, 9.3 km from Legoland Florida, and 9.6 km from Legoland Retreat, offering convenient access to local attractions.
The 202 square metre property sleeps 11 guests and boasts two bathrooms, a private fenced garden, a swimming pool, free Wi-Fi, and a fully equipped kitchen with a dishwasher; ideal for families visiting Legoland.

Best Winter Haven, FL holiday rentals with air conditioning

Big King Bed & 2 Queens: Legoland, Family Home - Winter Haven, FL
9.8 79 reviews

Big King Bed & 2 Queens: Legoland, Family Home

apartment, Winter Haven
This comfortable house is situated just 1.6km from Winter Haven's town centre and 4.8km from Legoland Florida, making it an ideal base for exploring the area's attractions. The house is close to several lakes, offering scenic views and opportunities for swimming and boating.
This three-bedroom property can accommodate up to seven guests, making it perfect for families or groups of friends. The house comes equipped with modern amenities including a fully equipped kitchen, a spacious living area, and a private backyard with a BBQ grill.
Nice Little Get-away - Winter Haven, FL
No reviews

Nice Little Get-away

house, Winter Haven
This two-bedroom detached property in Winter Haven offers garden views and is conveniently located 40 kilometres from Lakeland Linder International Airport.
This detached house accommodates up to eleven guests, featuring a fully equipped kitchen, air conditioning, free WiFi, and on-site private parking, with a washing machine for added convenience.
Cozy 1br Duplex Near Legoland® | Sleeps 4 - Winter Haven, FL
9.8 18 reviews

Cozy 1br Duplex Near Legoland® | Sleeps 4

apartment, Winter Haven
This one-bedroom flat is located in a quiet, central Winter Haven neighbourhood, offering convenient access to LEGOLAND® Florida, approximately 3.5 kilometres away.
This private duplex unit accommodates up to four guests and features a fully equipped kitchen, free Wi-Fi, and on-site parking, making it ideal for theme park visitors.
3br/2ba Lake Mariam Home Near Legoland With Kitchen & Laundry_1724 - Winter Haven, FL
9.7 410 reviews

3br/2ba Lake Mariam Home Near Legoland With Kitchen & Laundry_1724

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.
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