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

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.
4/2 House Near Legoland W Optional Heated Pool - Winter Haven, FL
9.9 107 reviews

4/2 House Near Legoland W Optional Heated Pool

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.
Eagle Haven Lake House - Winter Haven, FL
10 83 reviews

Eagle Haven Lake House

apartment, Eagle Lake
This waterfront holiday home is situated in Eagle Lake, Central Florida, a short 15-minute drive from Legoland and Orlando, offering easy access to Disney and Universal Studios. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a top choice for travellers.
The four-bedroom, two-bathroom apartment spans 157 square metres and comfortably accommodates up to eight guests. It features a fully equipped kitchen, a spacious living area, and a private garden with a Jacuzzi, perfect for enjoying the beautiful surroundings and relaxing after a day of exploring.
Lake, Pool, Hottub, Game Room, 8 Beds, Sleeps 17 - Winter Haven, FL
10 5 reviews

Lake, Pool, Hottub, Game Room, 8 Beds, Sleeps 17

apartment, Winter Haven
This spacious five-bedroom, three-bathroom apartment is situated waterfront in downtown Winter Haven, a mere 5-minute drive from Indigo's Family Fun Centre and Theatre Winter Haven.
Offering accommodation for up to 18 guests, this 269 square meter residence boasts a full kitchen, air conditioning, a swimming pool, jacuzzi, garden, spa, tennis court, and on-site activities including kayaking, golf, table tennis, and billiards.

Best Winter Haven, FL holiday rentals with parking

Peaceful Lakefront Oasis - Winter Haven, FL
9.8 33 reviews

Peaceful Lakefront Oasis

apartment, Winter Haven
This three-bedroom, two-bathroom lakeside house in Winter Haven, Florida, is less than 11 kilometres from Legoland Florida and minutes from the town centre.
Sleeping up to eight guests, this self-catering property boasts a fully equipped kitchen, direct lake access for watersports, a relaxing outdoor deck, and private parking; all within a completely private setting.
Tiny Paradise - Winter Haven, FL
9.6 14 reviews

Tiny Paradise

apartment, Winter Haven
This Winter Haven studio flat offers convenient access to Sertoma Park and Rotary Park, with Theatre Winter Haven and the Polk County Historical Museum within a reasonable driving distance (distances unspecified).
The self-catering studio, sleeping two guests, includes Wi-Fi, air conditioning, a full-size bed, and a kitchenette with a fridge and microwave; nearby activities include Chain of Lakes Park and Jump Florida Skydiving (distances unspecified).
Cozy 3br 2ba Winter Haven Getaway Chain Of Lakes Downtown - Winter Haven, FL
10 14 reviews

Cozy 3br 2ba Winter Haven Getaway Chain Of Lakes Downtown

apartment, Winter Haven
This three-bedroom, two-bathroom flat in Winter Haven is a mere 3-minute drive from Sertoma Park and Inman Park, with the Winter Haven Public Library a 12-minute walk away and Indigo's Family Fun Centre just 2 minutes by car.
This pet-friendly accommodation comfortably sleeps eight guests and features on-site laundry facilities, offering convenient access to local attractions such as Theatre Winter Haven, Bartow Airbase History Museum, Bok Tower Gardens, and LEGOLAND® Florida.
Luxury Staycomfy At Winterheaven - Winter Haven, FL
8.6 28 reviews

Luxury Staycomfy At Winterheaven

apartment, Winter Haven
This two-bedroom apartment in Winter Haven is ideally located just five minutes from the hospital, 14 minutes from LEGOLAND® Florida, 40 minutes from Disney World, and a short drive from the town centre. It has received very good guest ratings.
The apartment has a comfortable layout, sleeping up to six guests, and is perfect for families with a sofa bed and kids' colouring books. It comes with a well-equipped kitchen, a washing machine and dryer, a 50-inch TV with streaming services, and a welcome refreshment.

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

Cozy Bungalow - Winter Haven, FL
9.2 5 reviews

Cozy Bungalow

house, Winter Haven
This three-bedroom house in Winter Haven is situated 0.8km from the city centre and 8km from Legoland Florida.
The 132-square-metre property features a fully equipped kitchen, private balcony and garden, accommodates up to 15 guests, and includes free Wi-Fi.
The Old Haven - An Enduring Piece Of Nostalgia - Winter Haven, FL
9.8 15 reviews

The Old Haven - An Enduring Piece Of Nostalgia

apartment, Winter Haven
This lakeside property in Winter Haven is situated within 1.6 to 3.2 kilometres of Indigo's Billiards, Bowling & Games, Indigo's Family Fun Centre, Winter Haven Hospital, Winter Haven Women's Hospital, and Rotary Park.
This four-bedroom, two-bathroom holiday home boasts 167 square metres of living space, sleeping up to nine guests and offering a private balcony, garden, fitness centre, and fully equipped kitchen including a dishwasher; lakeside views and water activities are also available.
Getaway Clubhouse - Winter Haven, FL
9.4 13 reviews

Getaway Clubhouse

house, Winter Haven
This Winter Haven holiday home is situated 8km from Legoland Florida and 8km from Winter Haven's city centre, offering easy access to major attractions and multiple train stations within a 21km radius.
The 150 square metre property boasts three bedrooms, two bathrooms, sleeps fifteen guests, and includes a fully equipped kitchen with a dishwasher, a terrace, a garden, and free Wi-Fi.
Golfers Dream Home - Winter Haven, FL
9.4 3 reviews

Golfers Dream Home

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.

Best Winter Haven, FL holiday rentals with air conditioning

Spacious 3 Bed, 2 Bath Home Near Legoland - Winter Haven, FL
9.9 368 reviews

Spacious 3 Bed, 2 Bath Home Near Legoland

apartment, Winter Haven
This three-bedroom apartment is situated in Winter Haven, within walking distance of shops and restaurants, and a short drive from the city centre. The property has received excellent ratings for location, cleanliness and overall experience.
The apartment can accommodate up to eight guests and features a fully equipped kitchen with granite countertops, a private backyard with a grill, and two bathrooms. Guests can enjoy amenities such as keyless entry, comfortable bedding, ample closet space and air conditioning.
Brand New 2021 Guest House- Perfect For Long Stays - Winter Haven, FL
9.4 13 reviews

Brand New 2021 Guest House- Perfect For Long Stays

house, Winter Haven
This newly built Winter Haven guesthouse, located near various attractions, shops, and farmer's markets, offers convenient access to a lake within walking distance.
The self-catering studio, sleeping up to four guests, features a kitchenette with a fridge, microwave, portable stove, and air fryer, plus free Wi-Fi and dedicated parking.
3/2spacious-lakehomeaceloc4mileslegoland - Winter Haven, FL
9.6 423 reviews

3/2spacious-lakehomeaceloc4mileslegoland

apartment, Winter Haven
This three-bedroom apartment is situated just 3 kilometres from Winter Haven's city centre and hospital, and 6 kilometres from LEGOLAND and Peppa Pig Theme Park, offering a peaceful retreat close to attractions. Guests have consistently rated the apartment as excellent for its cleanliness, location, and overall experience.
The property comfortably accommodates up to 7 guests and features a fully equipped kitchen, laundry room, and a private outdoor space with a porch and yard. Guests can enjoy amenities such as Roku Smart TVs with streaming services, free coffee, tea, and bath products, as well as toys, plastic plates and utensils, a stroller, and designated parking.
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.
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