467 Holiday rentals and Airbnb in Winter Haven, FL
9.0 4 reviews
Winter Haven, FL
04/07 – 05/07
A$367/nightfor 1 night
The Old Haven - An Enduring Piece Of Nostalgia
4 4
house , Winter Haven
This four-bedroom house, The Old Haven, is situated in Winter Haven, Florida, 7.4 kilometres from Legoland Florida and within a 17-20 kilometre radius of various railway stations. The 167 square metre property boasts a fully equipped kitchen, private garden, fitness centre, and accommodates up to 17 guests, offering free Wi-Fi and luggage storage.
9.8 209 reviews
Winter Haven, FL
01/12 – 28/02
A$188/nighttotal: A$16732 (89 )
Legoland Lakehouse Canoe&kayak Retreat
1 2
apartment , Winter Haven
This charming apartment is situated in Winter Haven, just under two miles from Legoland, Chain of Lakes Fieldhouse, and the town centre, offering easy access to local attractions. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience. The apartment is spacious and comfortably accommodates up to six guests. It is equipped with a modern kitchen, a private swimming pool, and a lush garden, providing plenty of space for relaxation and entertainment.
8.4 31 reviews
Winter Haven, FL
02/07 – 06/07
A$505/nighttotal: A$2020 (4 )
Spacious 4-bedroom 2-bath Abode
4 9
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.
10 15 reviews
Winter Haven, FL
03/07 – 07/07
A$309/nighttotal: A$1236 (4 )
The Modern Retreat By Legoland
1 3
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.
9.9 26 reviews
Winter Haven, FL
07/07 – 12/07
A$292/nighttotal: A$1460 (5 )
Lovely Home On Lilac Lane - Winter Haven
1 4
apartment , Winter Haven
This three-bedroom, two-bathroom house in Winter Haven, Florida, is situated in a residential neighbourhood with a community pool and walking trail, 7.6km from Legoland Florida. The 3-bedroom property sleeps six guests comfortably, offering a full kitchen with dishwasher, air conditioning, free Wi-Fi, pet-friendly facilities and parking; two futon couches provide extra sleeping space.
9.8 303 reviews
Winter Haven, FL
04/07 – 05/07
A$368/nightfor 1 night
The Old Haven - An Enduring Piece Of Nostalgia
1 4
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.
9.8 44 reviews
Winter Haven, FL
02/07 – 06/07
A$1058/nighttotal: A$4232 (4 )
Costa 5bd Lego Themed Pool Home | Private Resort |
1 9
apartment , Cypress Gardens
This LEGO-themed holiday home is located in Cypress Gardens, a mere 5 minutes from LEGOLAND and within walking distance of various eateries. This spacious 5-bedroom, 3-bathroom villa accommodates up to 12 guests, boasting a private swimming pool, mini-golf, a pool table, and a BBQ bar, with major Orlando attractions like Disney World and Universal Studios accessible within 30-40 kilometres.
9.9 35 reviews
Winter Haven, FL
16/07 – 20/07
A$305/nighttotal: A$1220 (4 )
Luxury By Legoland 106
1 2
apartment , Winter Haven
This two-bedroom, two-bathroom apartment is situated in a brand-new luxury complex less than 1.6km from LEGOLAND® Florida Resort and Peppa Pig Theme Park in Winter Haven, Florida. The ground-floor flat sleeps six, boasts a fully equipped kitchen with dishwasher, in-unit laundry, and a LEGOLAND®-themed children's bedroom; resort amenities include a heated pool, fitness centre, and BBQ areas.
9.7 651 reviews
Winter Haven, FL
01/12 – 28/02
A$116/nighttotal: A$10324 (89 )
2 - Ships Ahoy Bungalow 2 Bed/2 Bath - Unit 17
1 2
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.
8.8 5 reviews
Winter Haven, FL
04/07 – 05/07
A$463/nightfor 1 night
4 Beds Near Legoland-adventhealth Fieldhouse
3 4
apartment , Winter Haven
This one-bedroom suite is situated conveniently close to Legoland, offering easy access to the popular theme park for families visiting Winter Haven. This flat provides a private kitchenette, air conditioning, parking, and accommodates up to two guests, making it a practical choice for those seeking a comfortable base for exploring local attractions and enjoying a restful stay.
9.9 16 reviews
Winter Haven, FL
27/06 – 04/07
A$253/nighttotal: A$1771 (7 )
Serene, Family Lakefront Home With Jacuzzi
1 2
apartment , Winter Haven
This two-bedroom, two-bathroom lakeside flat in Winter Haven, Florida, boasts direct access to the Chain of Lakes, offering excellent opportunities for boating and water sports. Sleeping up to seven guests, the property includes a fully equipped kitchen, washer/dryer, free parking, and access to kayaks, boats, and jet skis (guests must provide their own equipment).
9.9 15 reviews
Winter Haven, FL
08/07 – 12/07
A$179/nighttotal: A$716 (4 )
Cozy 1br Duplex Near Legoland® | Sleeps 4
1 3
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.
Best family friendly Winter Haven, FL holiday rentals
Among the 467 accommodations in Winter Haven, FL, here are the 4 best family friendly rentals
8.4 9 reviews
Winter Haven, FL
01/12 – 28/02
A$491/nighttotal: A$43699 (89 )
Cozy Lakefront Home W/ Pool -7 Mins From Legoland
3 2
apartment , Cypress Gardens
This three-bedroom, two-bathroom lakeside property in Winter Haven, near Cypress Gardens, is conveniently located approximately 8km from Legoland Florida and offers easy access to various attractions including Baytree Golf Club and Indigo's Family Fun Center. This family-friendly apartment, sleeping eight guests, boasts a private pool, gas grill, and Tulum-inspired design, alongside access to water sports on the lake and nearby nature reserves like KICCO Wildlife Management Area and The Circle B Bar Reserve.
8.4 62 reviews
Winter Haven, FL
01/12 – 28/02
A$224/nighttotal: A$19936 (89 )
3br Home | Near Legoland & Disney | Pool | Game Room | Pet-friendly | Balmoral Resort Amenities
3 2
resort , Haines City
This house is located in Haines City, just 5 kilometres from Southern Dunes Golf Club and Southern Dunes Golf and Country Club, and within 10 kilometres of Lake Henry Golf Club and True Blue Winery. The property has received excellent ratings for its location and cleanliness, and very good ratings for its overall quality. This three-bedroom house offers 169 square metres of space. The property has a private swimming pool, a fitness centre, a games room, a fully equipped kitchen, a garden, and a patio.
9.9 29 reviews
Winter Haven, FL
01/12 – 28/02
A$277/nighttotal: A$24653 (89 )
House On Eagle Lake - The Ultimate Family Getaway
1 2
apartment , Eagle Lake
This three-bedroom, two-bathroom lakefront property in Winter Haven, Florida, boasts direct Eagle Lake views and is situated 11.7km from Legoland Florida Resort and 6.6km from Winter Haven's town centre. The spacious house offers self-check-in, sleeps seven guests comfortably, includes a fully equipped kitchen with dishwasher, and features a patio with BBQ and yard games.
9.7 297 reviews
Winter Haven, FL
08/07 – 12/07
A$177/nighttotal: A$708 (4 )
The Russell Lake House
1 3
cottage , Winter Haven
This charming cabana is located in a peaceful neighbourhood in Winter Haven, Florida, just a short drive from attractions like Legoland Florida and the Polk Museum of Art. The property has received excellent ratings for user experience, location, and cleanliness. The comfortable cabana has one bedroom and one bathroom, accommodating up to four guests in a space of 37 square metres. The property features a private pool, a spacious backyard with lake views, and a dock offering direct access to the lake.
Best Winter Haven, FL holiday rentals with parking
10 1 review
Winter Haven, FL
16/07 – 20/07
A$437/nighttotal: A$1748 (4 )
Villa Sixteen Southern Dunes
4 2
apartment , Haines City
This four-bedroom, three-bathroom villa is located within the prestigious Southern Dunes Golf & Country Club in Haines City, Florida, offering convenient access to attractions such as LEGOLAND Florida, ChampionsGate Golf Club, and Reunion Resort Golf Course (distances to these attractions are not specified). The 167 square metre property boasts a private pool, spacious patio, modern kitchen, games room with pool table, and access to Southern Dunes' amenities including a championship golf course, fitness centre, and clubhouse; it comfortably sleeps eight guests.
10 1 review
Winter Haven, FL
08/07 – 12/07
A$391/nighttotal: A$1564 (4 )
260 M² House ∙ 5 Bedrooms ∙ 10 Guests
5 3
house , Winter Haven
This newly renovated, fully furnished lakefront property in Winter Haven offers convenient access to the area's chain of lakes and is situated just 16 kilometres from Legoland and within 64 kilometres of Orlando's attractions. This spacious dwelling accommodates up to six guests across four bedrooms and two bathrooms, featuring dual living spaces including a separate downstairs master suite with a second kitchen, complimentary high-speed WiFi, free parking, and an outdoor eating area with direct lake views.
9.8 20 reviews
Winter Haven, FL
16/07 – 20/07
A$181/nighttotal: A$724 (4 )
Historic Romance Studio B
1 2
studio , Haines City
This Haines City studio apartment, situated on the ground floor of a converted doctor's surgery, offers easy access to ChampionsGate and Southern Dunes golf courses, and is approximately a 30-minute drive from the Everglades Headwaters National Wildlife Refuge. The self-contained apartment sleeps two guests, features a microwave, air conditioning, parking, and Wi-Fi, and includes a private balcony overlooking trees; nearby attractions include Jump Florida Skydiving and Chain of Lakes Park.
10 8 reviews
Winter Haven, FL
03/07 – 07/07
A$344/nighttotal: A$1376 (4 )
Modern Comfort, Pet Friendly, 2 King Beds
2 3
apartment , Winter Haven
Chain of Lakes Cottage is situated in Winter Haven, Florida, near LEGOLAND Florida and Chain of Lakes Park, offering easy access to Havendale Plaza and Northgate Shopping Centre, approximately 0.6 km and 1.6 km away respectively. This six-bedroom, three-bathroom holiday home, boasting 175 square metres of floor space, sleeps five guests and includes on-demand linen and towel service, with nearby wildlife viewing opportunities at Circle B Bar Reserve and Sertoma Park.
Frequently asked questions about holiday 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 young children. The Polk Museum of Art is also a good option for families with older children, with interactive exhibits and a great collection of art. For a more active day out, head to the Winter Haven Recreational Complex, which has a playground, a splash pad, and a skate park.
What are 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. You'll avoid the crowds and the prices will be lower than during peak season.
What are the most popular Airbnbs in Winter Haven, FL?
What are the best budget-friendly activities in Winter Haven, FL?
For a free day out, head to the Chain of Lakes and go for a swim or a walk. The Winter Haven Public Library is also a great place to spend a few hours, with free Wi-Fi and a wide selection of books. If you're looking for a cheap bite to eat, check out the food trucks that gather at the Winter Haven Farmers Market.
What are the best holiday rentals with a pool in Winter Haven, FL?
What are the best restaurants with local dishes in Winter Haven, FL?
For a taste of authentic Florida cuisine, head to The Grove, which serves up fresh seafood and Southern comfort food. If you're looking for something a bit more casual, check out The Patio, which is known for its delicious burgers and fries.
What are the best rentals for families and kids in Winter Haven, FL?
What are the best walking or cycling routes in Winter Haven, FL?
The Chain of Lakes Trail is a great option for both walking and cycling, with stunning views of the lakes and the surrounding countryside. For a shorter walk, try the Winter Haven Downtown Walking Trail, which takes you past some of the city's historic buildings.
What are the best rentals or Airbnbs with a jacuzzi in Winter Haven, FL?
Are there pet-friendly attractions in Winter Haven, FL?
Yes, many of the parks and trails in Winter Haven are pet-friendly. Legoland Florida also welcomes well-behaved dogs on leads. For a dog-friendly dining experience, check out The Patio, which has a dog-friendly patio.
What are the benefits of choosing a vacation rental in Winter Haven, FL?
Vacation rentals offer more space and privacy than a hotel room, and they often come with amenities such as a kitchen and laundry facilities. They can also be a more affordable option, especially for families or groups.
What are the top sports attractions and facilities in Winter Haven, FL?
The Winter Haven Recreational Complex is a great place for families to enjoy a variety of sports activities, including baseball, softball, basketball, and tennis. The Chain of Lakes is also a popular spot for watersports, including boating, fishing, and swimming.
Destinations nearby
Best Winter Haven, FL holiday rentals with a balcony
Winter Haven, FL
02/07 – 06/07
A$1138/nighttotal: A$4552 (4 )
Costa Lego Pool Home - 5br Winter Haven Private Resort
5 9
house , Cypress Gardens
This private resort in Winter Haven offers a secluded experience, located approximately 4.8 kilometres from Swanns Railroad Station and 4.8 kilometres from Legoland Florida. This one-bedroom accommodation for up to 23 guests features air conditioning, complimentary WiFi, a fully equipped kitchen, a private swimming pool, and terrace access, with parking also provided.
9.7 18 reviews
Winter Haven, FL
03/07 – 07/07
A$703/nighttotal: A$2812 (4 )
Lanai And Pool Elegant Villa In Winter Haven!
4 3
house , Winter Haven
This four-bedroom villa is located in Winter Haven, just 5.3 kilometres from Swann's Railroad Station and 9.8 kilometres from Legoland Florida, offering easy access to local attractions. The property has received excellent ratings for location, cleanliness, and user experience. The 474 square metre villa comfortably accommodates up to eight guests. Guests can enjoy a private swimming pool, a terrace with stunning lake views, and a fully equipped kitchen with a dishwasher, microwave, and washing machine.
10 11 reviews
Winter Haven, FL
16/07 – 20/07
A$193/nighttotal: A$772 (4 )
Historic Desire Studio D
1 2
studio , Haines City
This stylish Haines City studio apartment is situated on the second floor of a converted doctor's office building, offering convenient access to attractions such as LEGOLAND Florida and ChampionsGate Golf Club (distances to these attractions are not specified). The self-catering unit features a private balcony, a dedicated workspace, a 43" TV with cable and Roku, free on-site parking, and accommodates up to two guests, with a shared backyard and courtyard available.
10 3 reviews
Winter Haven, FL
16/07 – 20/07
A$203/nighttotal: A$812 (4 )
Historic Love, Modern Appeal C
1 2
apartment , Haines City
This studio apartment is located on the second floor of a repurposed doctor's office in Haines City, just 10km from LEGOLAND® Florida and Indigo's Family Fun Center, offering a quiet and unique stay with a touch of history. The apartment provides a comfortable and modern feel with stylish decor, perfect for a couple seeking a peaceful retreat. The accommodation has a private balcony overlooking tall trees, ideal for enjoying a relaxing moment. Guests can also enjoy the convenience of a fully equipped kitchen with a fridge and microwave oven, as well as air conditioning and free Wi-Fi.
Best Winter Haven, FL holiday rentals with air conditioning
8.8 66 reviews
Winter Haven, FL
03/07 – 07/07
A$292/nighttotal: A$1168 (4 )
Legoland 3 Bedroom Pool Home. Pet Friendly!
3 3
apartment , Winter Haven
This spacious apartment is conveniently located just 2.1 miles from Legoland, making it ideal for families visiting the theme park. It has consistently received very good ratings for cleanliness, location, and overall satisfaction. The property offers a comfortable and modern living space, suitable for up to 13 guests. Enjoy amenities such as a fully equipped kitchen, air conditioning, a swimming pool, and free parking, as well as smart TVs in every room and two bathrooms.
9.9 37 reviews
Winter Haven, FL
16/07 – 20/07
A$129/nighttotal: A$516 (4 )
New Modern Guest House! Great Location. Smoke-free
1 2
house , Dundee
This Dundee guesthouse, perfect for a family break, offers a private entrance and is conveniently located near Dundee's city centre. The self-catering property sleeps four, boasting a queen bed, sofa bed, fridge, freezer, microwave, Wi-Fi, and parking; USB charging ports add extra convenience.
10 5 reviews
Winter Haven, FL
03/07 – 07/07
A$302/nighttotal: A$1208 (4 )
Grammy's House On Lake Buckeye
3 3
apartment , Winter Haven
This mid-century flat is directly situated on the lake in Winter Haven, offering picturesque views and waterfront access, with convenient access to Winter Haven's renowned chain of lakes and local attractions. This spacious accommodation, ideal for families and accommodating up to six guests, features three bedrooms, two bathrooms, air conditioning, and a kitchen equipped with a fridge and dishwasher, perfect for both short and extended stays.
10 2 reviews
Winter Haven, FL
03/07 – 07/07
A$247/nighttotal: A$988 (4 )
Cozy Bungalow
3 3
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.
