Compare Vacation Rentals & Airbnb in Winter Haven, FL
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467 Rentals and Airbnb in Winter Haven, FL
Winter Haven, FL
01/12 – 28/02
$123/nighttotal: $10947 (89 )
Modern Winter Haven Apartment
1 2
apartment , Winter Haven
This fully furnished two-bedroom, two-bathroom apartment in Winter Haven offers convenient proximity to local hospitals, schools, and shopping centres, although precise distances aren't specified. The recently renovated property features a modern interior, in-unit laundry facilities, private parking, and comfortably accommodates two guests; amenities include a fridge, freezer, microwave, and air conditioning.
9.4 74 reviews
Winter Haven, FL
25/06 – 29/06
$380/nighttotal: $1520 (4 )
4 Bedroom, Legoland, Pet Friendly, Pool, Gameroom
1 5
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.
9.4 88 reviews
Winter Haven, FL
10/07 – 11/07
$254/nightfor 1 night
Stylish-n-private 1br Retreat 2 Miles To Legoland
1 4
apartment , Cypress Gardens
Wakulla Vacation Home (2) is a duplex located just 3.2 kilometres from downtown Winter Haven, close to LEGOLAND Florida Theme Park, Peppa Pig World, and Winter Haven Hospital. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. The apartment is suitable for families, with a capacity of four guests. Amenities include a fully equipped kitchen, a spacious yard, a private back patio, and a dedicated workstation, ensuring a comfortable and convenient stay.
10 15 reviews
Winter Haven, FL
25/06 – 29/06
$303/nighttotal: $1212 (4 )
The Modern Retreat By Legoland
1 5
apartment , Winter Haven
This four-bedroom, two-bathroom apartment is situated near Winter Haven, Florida, approximately 4.5 kilometres from LEGOLAND Florida. Sleeping eight guests comfortably, this family-friendly property boasts a fully equipped kitchen with fridge, microwave, and dishwasher, plus air conditioning, parking, and internet access; toddler essentials such as a crib and double stroller are also provided.
8.4 31 reviews
Winter Haven, FL
25/06 – 29/06
$393/nighttotal: $1572 (4 )
Spacious 4-bedroom 2-bath Abode
4 5
house , Winter Haven
This comfortable house is located in Winter Haven, Florida, just 11 kilometres from Swanns Railroad Station and Legoland Florida. The property has received excellent ratings for its cleanliness, location, and overall user experience. The house has four bedrooms and two bathrooms, spanning 214 square metres. It offers a range of amenities, including a fully equipped kitchen, a relaxing garden, air conditioning, free Wi-Fi, and private parking.
8.6 52 reviews
Winter Haven, FL
01/12 – 28/02
$135/nighttotal: $12015 (89 )
Central Private King Suit Washer Dryer 2 Miles To Hospital
1 2
apartment , Winter Haven
This Winter Haven apartment is conveniently located 3.2km from a hospital and 8.8km from Legoland Florida, ideal for medical visits or theme park trips. The 42-square-metre self-catering flat features a king suite, a fully equipped kitchenette with microwave and fridge, in-unit laundry, free Wi-Fi, and private parking, sleeping up to five guests.
9.8 71 reviews
Winter Haven, FL
20/06 – 27/06
$189/nighttotal: $1323 (7 )
Big King Bed & 2 Queens: Legoland, Family Home
1 2
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.
9.6 8 reviews
Winter Haven, FL
25/06 – 29/06
$318/nighttotal: $1272 (4 )
Newly Remodeled Lakefront Vacation Home On The Chain Of Lakes In Winter Haven
2 5
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.
9.9 51 reviews
Winter Haven, FL
10/07 – 11/07
$377/nightfor 1 night
Getaway Clubhouse 5 Mil Legoland & .5 Mil Downtown
1 4
apartment , Winter Haven
This family-friendly holiday home in Winter Haven, Florida offers three bedrooms and two bathrooms, sleeping up to eight guests, and is conveniently located near various attractions (exact distances require a specific address). The property boasts a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, plus a garden, air conditioning, internet access, parking, and ample indoor entertainment such as board games and a foosball table.
8.8 7 reviews
Winter Haven, FL
25/06 – 29/06
$316/nighttotal: $1264 (4 )
Serene Lakeside Retreat- 3 Bdr Romantic Getaway
3 5
house , Winter Haven
This lakeside house in Winter Haven, Florida, is situated 16km from Legoland Florida and 24km from various railway stations, offering serene views. The 179 square metre property sleeps up to 11 guests, boasting three bedrooms, two bathrooms, a fully equipped kitchen, a garden, terrace, free Wi-Fi, private parking, and children's amenities including an indoor play area and outdoor equipment.
9.6 413 reviews
Winter Haven, FL
25/06 – 29/06
$237/nighttotal: $948 (4 )
★3/2★spacious-lakehome☀aceloc☀4miles🎢legoland🎢
1 5
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.
10 2 reviews
Winter Haven, FL
25/06 – 29/06
$243/nighttotal: $972 (4 )
Cozy Bungalow
3 5
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.
Best family friendly Winter Haven, FL vacation rentals
Among the 467 accommodations in Winter Haven, FL, here are the 4 best family friendly rentals
8.6 26 reviews
Winter Haven, FL
01/12 – 28/02
$133/nighttotal: $11837 (89 )
Luxury Staycomfy At Winterheaven
2 2
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.
Winter Haven, FL
25/06 – 29/06
$286/nighttotal: $1144 (4 )
4br 3bath Pool Home With Golf Course View, Quiet Cul De Sac In Southern Dunes
4 5
house , Haines City
This 4-bedroom, 3-bathroom pool villa is located in a quiet cul-de-sac in Southern Dunes, Haines City, offering a golf course view and situated 14 kilometres from Legoland Florida and 14 kilometres from Swanns Railroad Station. This spacious 144 square metre holiday home accommodates up to 12 guests and features a private swimming pool, a fully equipped kitchen with a dishwasher, complimentary Wi-Fi, and an outdoor dining area.
9.9 240 reviews
Winter Haven, FL
10/07 – 11/07
$224/nightfor 1 night
Cedar Cottage
1 4
cabin , Cypress Gardens
This cedarwood cottage is situated in a peaceful residential neighbourhood in Cypress Gardens, just 6 kilometres from Legoland and within 6 kilometres of numerous restaurants and shops including Publix, Starbucks and Walmart. The one-bedroom cabin offers a private fenced-in area with a picnic table and firepit, a landscaped courtyard with a small fish pond and a spacious feel despite its 42 square metre size.
9.8 81 reviews
Winter Haven, FL
25/06 – 29/06
$377/nighttotal: $1508 (4 )
Modern 3br Home
1 5
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.
Best Winter Haven, FL vacation rentals with parking
Winter Haven, FL
25/06 – 29/06
$453/nighttotal: $1812 (4 )
White Door House!
1 5
house , Winter Haven
This detached property is located in Winter Haven, offering convenient access to Swanns Railroad Station (3.4 kilometres) and Legoland Florida (9.9 kilometres). This detached house provides complimentary private parking, free WiFi, a fully equipped kitchen, and accommodates up to 15 guests across 167 square metres with 1 bedroom and 2 bathrooms.
9.0 2 reviews
Winter Haven, FL
20/06 – 27/06
$265/nighttotal: $1855 (7 )
Golf Course Views Southern Dunes Pool Villa Large Pool Deck
3 2
house , Haines City
This Haines City villa is situated near the Southern Dunes Golf Course, 13.4km from Swann's Railroad Station and 24km from Legoland Florida, offering convenient access to local attractions and historical sites. The 162 square metre, three-bedroom property sleeps up to ten guests and boasts a private pool, garden, fully equipped kitchen, air conditioning, Wi-Fi, and in-house laundry facilities.
10 10 reviews
Winter Haven, FL
10/07 – 11/07
$520/nightfor 1 night
Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain Of Lakes
3 4
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.
10 2 reviews
Winter Haven, FL
10/07 – 11/07
$410/nightfor 1 night
Cozy Bungalow - 5 Mi Legoland & 0.5 Mi Dwntwn
3 4
apartment , Winter Haven
This lakeside property in Winter Haven is situated approximately 1.6km from Winter Haven Women's Hospital and within 1.6km of family attractions such as Indigo's Family Fun Centre and Rotary Park. This three-bedroom, three-bathroom holiday home offers 132 square metres of living space, sleeping up to eight guests, and features a fully equipped kitchen, laundry facilities, a terrace, and barbecue grills; lakeside views and water activities are also available.
Frequently Asked Questions about vacation rentals in Winter Haven, FL
What are the top family-friendly attractions in Winter Haven, FL?
Legoland Florida is a must-visit for families, with rides, shows, and a water park. The Polk Museum of Art is also a great option, with interactive exhibits and art for all ages. And the Winter Haven Public Library is a great place for kids to spend an afternoon with books and activities.
What are the best Airbnb and vacation 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 is during the spring or fall. The weather is still pleasant, but the crowds are smaller and the prices are lower. You can also try booking a few weeks in advance, especially if you're planning to visit during 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?
The annual Chain of Lakes Festival is a big event with lots of music, food, and activities. The Winter Haven Art Festival is another popular event, showcasing local artists and crafts. And the Legoland Florida theme park hosts various special events throughout the year.
What are the best vacation rentals with a pool in Winter Haven, FL?
What are the best budget-friendly activities in Winter Haven, FL?
You can take a leisurely walk or bike ride around the Chain of Lakes. There are plenty of parks and green spaces to enjoy, like the Central Park and the Lake Howard Nature Park. You can also visit the Winter Haven Public Library, which is free and has a variety of programs and exhibits.
What are the best rentals for families and kids in Winter Haven, FL?
What are the best restaurants with local dishes in Winter Haven, FL?
For a taste of local cuisine, try The Grove, they have a great menu of fresh seafood and Southern comfort food. Another great option is The Boathouse Restaurant, they have a beautiful view of the lake and serve up delicious seafood and steaks.
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, it's about 20 km long and goes around all the lakes in the area. You can also try the Winter Haven Linear Park, it's a paved trail that runs along the CSX railroad tracks.
Are there pet-friendly attractions in Winter Haven, FL?
Yes, many of the parks in Winter Haven are pet-friendly. The Central Park and the Lake Howard Nature Park both have designated areas for dogs. Legoland Florida also has a few pet-friendly areas.
What are the benefits of choosing a vacation rental in Winter Haven, FL?
Vacation rentals offer more space and privacy than a hotel room. They often have kitchens, so you can save money on food by cooking your own meals. And they're often located in more residential areas, so you can get a better feel for the local culture.
What are the top sports attractions and facilities in Winter Haven, FL?
Winter Haven is known for its golf courses, with many public and private courses available. The Chain of Lakes is also a popular spot for water sports, like boating, fishing, and waterskiing. There's also a local YMCA with a range of fitness classes and a swimming pool.
Destinations nearby
Best Winter Haven, FL vacation rentals with a balcony
9.4 28 reviews
Winter Haven, FL
20/06 – 27/06
$252/nighttotal: $1764 (7 )
Game Room + Fenced Yard: Home Near Disney World!
4 2
house , Haines City
This four-bedroom holiday home is situated in Haines City, Florida, just 14 kilometres from Swanns Railroad Station and 26 kilometres from Legoland Florida. The property has received excellent reviews for its cleanliness, location, and overall user experience. This spacious house offers 268 square metres of living space and can comfortably accommodate up to 10 guests. It features a well-equipped kitchen, a relaxing patio, a games room, and modern amenities such as air conditioning, a washing machine, a dishwasher, and free Wi-Fi.
Winter Haven, FL
20/06 – 27/06
$280/nighttotal: $1960 (7 )
Golf Course Views, Southern Dunes Pool Villa, Large Pool Deck
3 2
apartment , Haines City
This Haines City holiday home is situated near Southern Dunes Golf Club and Country Club, less than 5 km away, offering easy access to golfing and a 5 km drive to Ember Dog Park. This 162 square metre property sleeps six guests and boasts three bedrooms, two bathrooms, a private pool, fully equipped kitchen, in-unit laundry, and a terrace; enjoy self-catering convenience and proximity to local amenities.
8.5 31 reviews
Winter Haven, FL
10/07 – 11/07
$173/nightfor 1 night
Cozy Cove Stay
1 4
apartment , Winter Haven
This Winter Haven flat is conveniently located approximately 6km from Swanns Railroad Station and 13km from Legoland Florida, offering easy access to local attractions. The one-bedroom, one-bathroom apartment sleeps seven guests and includes a fully equipped kitchen, free Wi-Fi, private parking, and a balcony; nearby amenities include several other railway stations within a 19km radius.
Winter Haven, FL
20/06 – 27/06
$314/nighttotal: $2198 (7 )
Private, Large Pool Villa, Southern Dunes, Golf Course Views
4 2
apartment , Haines City
This four-bedroom, three-bathroom holiday home in Haines City, Florida, enjoys a golf-front position near Southern Dunes Golf Course and is within a 24-48 km drive of major Orlando theme parks including Legoland Florida, Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando. The property offers a private pool (with optional heating), high-speed WiFi (200 Mbps download), a fully equipped kitchen, laundry facilities, and sleeps eight guests, making it ideal for families or groups visiting the area.
Best Winter Haven, FL vacation rentals with air conditioning
9.0 42 reviews
Winter Haven, FL
20/06 – 27/06
$133/nighttotal: $931 (7 )
*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.
10 1 review
Winter Haven, FL
01/12 – 28/02
$113/nighttotal: $10057 (89 )
Sunset Upgrade Included
1 2
house , Winter Haven
This furnished flat offers lakeside living on Lake Howard, within walking distance of Winter Haven's town centre and under 1 kilometre from Winter Haven Hospital. This one-bedroom flat accommodates two guests and features a kitchen, air conditioning, and onsite laundry for an additional fee, with internet access and pets welcome.
9.0 13 reviews
Winter Haven, FL
10/07 – 11/07
$255/nightfor 1 night
Private/spacious 1br Central Near Legoland 2 Miles
1 4
apartment , Cypress Gardens
This one-bedroom duplex apartment is located in Winter Haven, Florida, just 3.2 kilometres from downtown Winter Haven, the hospital, LEGOLAND, and Peppa Pig Theme Park, making it an ideal base for exploring the area. It has received excellent user ratings, with guests praising its cleanliness, safety, and friendly service. The apartment comfortably accommodates five guests and features a private screened-in porch, a large fenced-in yard, and access to nearby golf courses, shopping centres, and entertainment options. Guests can enjoy the Florida weather on the porch, relax in the spacious yard, and easily access attractions like Cypress Gardens, which is just a short drive away.
10 19 reviews
Winter Haven, FL
01/12 – 28/02
$152/nighttotal: $13528 (89 )
Winter Haven 2 Br 2 Ba Condo 2 On Chain Of Lakes
2 2
apartment , Winter Haven
This two-bedroom, two-bathroom apartment is located on the shores of Lake Lulu in Winter Haven, offering stunning lake views and a peaceful setting just a short walk from local restaurants. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment is ideal for families or groups of up to four guests, featuring a spacious master suite with a king-size bed. Guests can enjoy a range of amenities, including a swimming pool, fitness centre, and a fully equipped kitchen with stainless steel appliances.
