467 Holiday rentals and Airbnb in Winter Haven, FL
9.9 35 reviews
Winter Haven, FL
27/06 – 04/07
A$261/nighttotal: A$1827 (7 )
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.
10 2 reviews
Winter Haven, FL
02/07 – 06/07
A$461/nighttotal: A$1844 (4 )
Game, Swim & Unwind: Lakeside Retreat Near Disney
5 9
apartment , Haines City
This five-bedroom, three-bathroom holiday home in Haines City, Florida, is located a short 8km drive from both Southern Dunes Golf Club and Southern Dunes Golf & Country Club. The 251-square-metre property offers a private pool, garden, and parking, accommodating up to 10 guests and including a fully equipped kitchen, laundry facilities, and internet access.
10 11 reviews
Winter Haven, FL
16/07 – 20/07
A$272/nighttotal: A$1088 (4 )
Nice Little Get•a•way
1 2
apartment , Winter Haven
This two-bedroom flat in Winter Haven offers convenient access, being just 5 minutes' drive from Legoland and a short distance to major supermarkets like Publix, Aldi, and Walmart. The property features air conditioning, a kitchen, parking, and internet, with a guest capacity of four, and is ideally situated for exploring Bok Tower Gardens and enjoying a peaceful family holiday.
Winter Haven, FL
27/06 – 04/07
A$195/nighttotal: A$1365 (7 )
Downtown Winter Haven Retreat | Arcade + Fast Wifi
3 2
apartment , Winter Haven
This downtown Winter Haven flat offers direct access to local shops and eateries, situated just moments from attractions. This three-bedroom residence accommodates up to five guests, featuring a fully equipped kitchen, air conditioning, a garden, and an arcade machine for entertainment.
8.6 8 reviews
Winter Haven, FL
07/07 – 12/07
A$202/nighttotal: A$1010 (5 )
3bed 2bath Spacious-lakehomeaceloc4mileslegoland
3 4
house , Winter Haven
This Cypress Gardens lakefront property in Winter Haven is situated 6.6km from Legoland Florida and within 22.5km of several railway stations. The 153 square metre house offers a spacious three-bedroom, two-bathroom layout sleeping up to 13 guests, complete with a fully equipped kitchen, free Wi-Fi, laundry facilities, and private parking.
8.6 52 reviews
Winter Haven, FL
27/06 – 04/07
A$153/nighttotal: A$1071 (7 )
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.
9.5 12 reviews
Winter Haven, FL
02/07 – 06/07
A$585/nighttotal: A$2340 (4 )
The Best House
1 9
apartment , Winter Haven
This four-bedroom house, situated in Winter Haven's Riverwood Circle neighbourhood, is approximately 16km from LEGOLAND Florida Resort and Peppa Pig Theme Park, and close to the Chain of Lakes for watersports. The property boasts a spacious layout sleeping up to 10 guests, offering a swimming pool, garden, fitness centre, parking, and a fully equipped kitchen including a dishwasher, alongside complimentary internet access.
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.
9.9 358 reviews
Winter Haven, FL
27/06 – 04/07
A$232/nighttotal: A$1624 (7 )
Spacious 3 Bed, 2 Bath Home Near Legoland
1 2
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.
10 18 reviews
Winter Haven, FL
27/06 – 04/07
A$143/nighttotal: A$1001 (7 )
Winter Haven Apt: 1 Mi To Polk State College!
1 2
apartment , Winter Haven
This Winter Haven apartment is conveniently located less than 1.6km from Rotary Park and Winter Haven Hospital, and under 4.8km from Winter Haven Women's Hospital and Indigo's Family Fun Center. This 50 square metre, two-bedroom flat sleeps two guests and boasts a furnished kitchen, private balcony, free Wi-Fi, on-site parking, and a shared playground.
9.9 51 reviews
Winter Haven, FL
07/07 – 12/07
A$240/nighttotal: A$1200 (5 )
Getaway Clubhouse 5 Mil Legoland & .5 Mil Downtown
3 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.
9.4 16 reviews
Winter Haven, FL
14/07 – 11/08
A$229/nighttotal: A$6412 (28 )
Winter Heaven Lakefront House
1 2
apartment , Winter Haven
This three-bedroom, two-bathroom house in Winter Haven is situated opposite Polk College, less than a few kilometres from Legoland Florida, Walmart, and the historic downtown area. Sleeping up to nine guests, this property boasts a private swimming pool, excellent user ratings, and is within easy reach of various restaurants and shopping facilities.
Best family friendly Winter Haven, FL holiday rentals
Among the 467 accommodations in Winter Haven, FL, here are the 4 best family friendly rentals
9.8 83 reviews
Winter Haven, FL
03/07 – 07/07
A$384/nighttotal: A$1536 (4 )
Modern 3br Home
3 3
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.
9.5 50 reviews
Winter Haven, FL
16/07 – 20/07
A$378/nighttotal: A$1512 (4 )
Lovely Home In Southern Dunes Golf & Country Club Gated Community
4 2
house , Haines City
This four-bedroom house is situated in the Southern Dunes Golf & Country Club gated community in Haines City, just 14 kilometres from Swanns Railroad Station (Historical) and 24 kilometres from Legoland Florida. The property has consistently received excellent ratings for location, cleanliness and overall user experience. The 158 square metre dwelling comfortably accommodates up to ten guests and features a fully equipped kitchen, a private pool, a fitness centre, and a relaxing garden. Guests can also enjoy access to a golf course, an on-site restaurant, and outdoor play equipment for children.
This one-bedroom apartment is conveniently located in Winter Haven, within a 3-mile radius of Rotary Park, Winter Haven Hospital, Lake Conine, Inman Park, and Winter Haven Women's Hospital. The property has received very good user ratings, making it a popular choice for travellers. The apartment is suitable for up to three guests and includes a fully equipped kitchen with a refrigerator, oven, and microwave. Guests can enjoy free Wi-Fi, a smart TV, and parking, making it a comfortable and convenient choice for exploring Winter Haven.
9.9 20 reviews
Winter Haven, FL
16/07 – 20/07
A$265/nighttotal: A$1060 (4 )
Legoland Escape
4 2
apartment , Cypress Gardens
This family-friendly apartment in Cypress Gardens offers unbeatable proximity to LEGOLAND Florida, just a 2-minute drive (approximately 320 meters) away. This spacious four-bedroom property accommodates up to eight guests and features a private swimming pool, a garden with a fire pit, and a fully equipped kitchen, ensuring a comfortable stay with home comforts.
Best Winter Haven, FL holiday rentals with parking
8.4 62 reviews
Winter Haven, FL
03/07 – 07/07
A$350/nighttotal: A$1400 (4 )
3br Home | Near Legoland & Disney | Pool | Game Room | Pet-friendly | Balmoral Resort Amenities
3 3
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.
9.8 32 reviews
Winter Haven, FL
27/06 – 04/07
A$257/nighttotal: A$1799 (7 )
Game Room + Fenced Yard: Home Near Disney World!
4 2
apartment , Haines City
This family-friendly holiday home is located just 5km from Southern Dunes Golf Club and 10km from Lake Henry Golf Club, making it ideal for golfers seeking a relaxing escape. It has received excellent user ratings, with guests praising its comfort and amenities. The property spans 268 square metres and comfortably accommodates up to 10 guests. Enjoy a range of features, including a fully equipped kitchen, a patio, a garden, and a tennis court, ensuring a comfortable and enjoyable stay for all.
10 11 reviews
Winter Haven, FL
27/06 – 04/07
A$144/nighttotal: A$1008 (7 )
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.
9.8 7 reviews
Winter Haven, FL
03/07 – 07/07
A$297/nighttotal: A$1188 (4 )
Bright Cypress Gardens Home Near Legoland!
3 3
house , Cypress Gardens
This Cypress Gardens holiday home is situated 3.4 kilometres from Legoland Florida, offering convenient access to the theme park and other historical railway stations within a 24-kilometre radius. The 137-square-metre property boasts three bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus free Wi-Fi, air conditioning, and private parking.
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
16/07 – 20/07
A$359/nighttotal: A$1436 (4 )
Updated Pool Villa - Southern Dunes
1 2
house , Haines City
This detached villa, the Updated Pool Villa - Southern Dunes, is situated in Haines City, offering direct access to local attractions and amenities. Spanning 180 square meters, this family-friendly residence features a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a terrace, and on-site parking, with complimentary Wi-Fi available for guests.
10 3 reviews
Winter Haven, FL
14/07 – 11/08
A$142/nighttotal: A$3976 (28 )
Winter Haven Apt 1 Mi To Polk State College!
1 2
apartment , Winter Haven
This one-bedroom flat is located just 1.6 kilometres from Polk State College in Winter Haven, making it ideal for students, faculty, or families visiting students. It is also within easy reach of attractions like Legoland Florida (6.7 kilometres) and Swanns Railroad Station (5.6 kilometres). The property enjoys excellent guest ratings for its cleanliness, location, and overall experience. This 50 square metre flat comfortably accommodates two guests and boasts a fully equipped kitchen, a balcony, and free Wi-Fi. Enjoy amenities like air conditioning, a flat-screen TV, and towels and bed linen provided, ensuring a comfortable and enjoyable stay.
Winter Haven, FL
16/07 – 20/07
A$379/nighttotal: A$1516 (4 )
Magic Poolside Retreat
4 2
house , Haines City
This Haines City villa is situated within a 6-kilometre radius of Southern Dunes Golf Club and Country Club, offering convenient access to both golf courses and regional medical facilities. This four-bedroom, two-bathroom property boasts 154 square metres of living space, a private balcony, swimming pool, and free Wi-Fi, comfortably accommodating up to eight guests and including on-site laundry facilities.
8.3 1815 reviews
Winter Haven, FL
08/07 – 12/07
A$598/nighttotal: A$2392 (4 )
Legoland® Florida Resort
1 3
resort , Winter Haven
LEGOLAND® Florida Resort is located in Winter Haven, Florida, just a short drive from attractions like Historic Bok Tower Gardens and Davidson of Dundee candy factory. The resort is highly rated for its location, cleanliness, and overall experience, making it a popular choice for families. The resort offers a variety of accommodation options, including themed rooms and bungalows. Guests can enjoy a range of amenities, including swimming pools, restaurants, bars, and a concierge service. There are also family-friendly activities such as treasure hunts, LEGO® model building sessions, and nightly entertainment.
Best Winter Haven, FL holiday rentals with air conditioning
8.0 5 reviews
Winter Haven, FL
02/07 – 06/07
A$731/nighttotal: A$2924 (4 )
Brand New Home Near Legoland & The Chain Of Lakes
1 9
apartment , Eagle Lake
This apartment in Eagle Lake offers a prime location, situated approximately 16 kilometres from Legoland, Peppa Pig World, and Sea Life Aquarium, and a 56-kilometre drive from Disney World. This four-bedroom, two-bathroom residence accommodates up to ten guests and features a resort-style swimming pool, a fitness centre, and convenient access to the chain of lakes and Tampa.
10 1 review
Winter Haven, FL
02/07 – 06/07
A$391/nighttotal: A$1564 (4 )
260 M² House ∙ 5 Bedrooms ∙ 10 Guests
5 9
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.
9.6 151 reviews
Winter Haven, FL
27/06 – 04/07
A$230/nighttotal: A$1610 (7 )
Cozy Bungalow - 5 Mi Legoland & 0.5 Mi Dwntwn
1 2
apartment , Winter Haven
This charming bungalow sits in the heart of downtown Winter Haven, just a short walk from the entertainment district and a stone's throw from shops and restaurants. The property has consistently received excellent ratings for its location, cleanliness, and user experience. The home is a three-bedroom, one-bathroom property that comfortably accommodates up to eight guests. The apartment offers a fully equipped kitchen, a washer and dryer, a cozy patio, and a range of amenities for both families and working professionals, including games, a baby chair, a crib, and a dedicated work space.
9.7 6 reviews
Winter Haven, FL
27/06 – 04/07
A$282/nighttotal: A$1974 (7 )
Work, Play Or Recharge:3br Pool Home Near Legoland
3 2
apartment , Winter Haven
This newly remodelled detached residence is situated in a quiet, private area of Winter Haven, offering a peaceful retreat with easy access to local attractions. This detached residence features three bedrooms, two bathrooms, and accommodates up to five guests, boasting a private swimming pool, a fully equipped kitchen, a dedicated workspace, an enclosed patio, in-home laundry, and a charcoal grill poolside.