467 Holiday rentals and Airbnb in Winter Haven, FL
9.8 173 reviews
Winter Haven, FL
08/07 – 12/07
185 €/nighttotal: 740 € (4 )
3/2 Great Family Home Near Legoland
1 3
apartment , Winter Haven
This apartment is conveniently located in Winter Haven, just 6.4 kilometres from Legoland and 2.2 kilometres from Winter Haven Hospital. The property has received excellent ratings for user experience, location, and cleanliness. The home has three bedrooms and two bathrooms, comfortably accommodating up to seven guests. It offers a range of amenities, including a garden, parking, Wi-Fi, air conditioning, and a kitchen with a fridge, making it ideal for a comfortable and enjoyable stay.
9.4 16 reviews
Winter Haven, FL
02/07 – 06/07
449 €/nighttotal: 1796 € (4 )
Winter Heaven Lakefront House
1 9
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.
10 2 reviews
Winter Haven, FL
02/07 – 06/07
280 €/nighttotal: 1120 € (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 38 reviews
Winter Haven, FL
27/06 – 04/07
158 €/nighttotal: 1106 € (7 )
Luxury By Legoland 104
1 2
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.
9.3 59 reviews
Winter Haven, FL
17/07 – 24/07
156 €/nighttotal: 1092 € (7 )
Hook, Line And Leisure Lakefront Gem With Porch!
3 2
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.
9.8 14 reviews
Winter Haven, FL
08/07 – 12/07
158 €/nighttotal: 632 € (4 )
The Old Haven - An Enduring Piece Of Nostalgia
4 3
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.
9.7 23 reviews
Winter Haven, FL
16/07 – 20/07
83 €/nighttotal: 332 € (4 )
Winter Haven Guest Suite
1 2
house , Cypress Gardens
This self-contained studio apartment is located in a peaceful Cypress Gardens neighbourhood, 2.25km from Legoland Florida. The 550 sq ft property features a queen bed, daybed with trundle, kitchenette with microwave and air fryer, private deck, garden, parking, Wi-Fi, and accommodates up to five guests.
9.5 12 reviews
Winter Haven, FL
02/07 – 06/07
355 €/nighttotal: 1420 € (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
03/07 – 07/07
158 €/nighttotal: 632 € (4 )
Cozy Castle- 2-bedroom House In Serene Winter Haven With Ac
2 3
apartment , Winter Haven
This Spanish Gothic residence, a century-old property, is centrally situated in Winter Haven, offering convenient access to LEGOLAND Florida, Bok Tower Gardens, and the Chain-of-Lakes, with Winter Haven Airport approximately 3 kilometres away. This two-bedroom flat accommodates up to six guests and features air conditioning and internet, ideal for families or couples, providing a comfortable base for exploring Polk County attractions such as the Lake Myrtle Sports Complex and Florida Southern College.
9.8 303 reviews
Winter Haven, FL
08/07 – 12/07
145 €/nighttotal: 580 € (4 )
The Old Haven - An Enduring Piece Of Nostalgia
1 3
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.
9.0 20 reviews
Winter Haven, FL
08/07 – 12/07
141 €/nighttotal: 564 € (4 )
Lovely Spanish Style Home
1 3
apartment , Winter Haven
This historic 100-year-old Spanish-style residence is located in Winter Haven, 100 metres from Lake Howard and close to Peace River Park, with downtown Winter Haven attractions five minutes away. This two-bedroom, two-bathroom flat accommodates up to four guests and offers essential amenities including internet, air conditioning, a kitchen, and parking, with the Central Florida chain of lakes ideal for boating and fishing nearby.
9.4 76 reviews
Winter Haven, FL
03/07 – 07/07
250 €/nighttotal: 1000 € (4 )
4 Bedroom, Legoland, Pet Friendly, Pool, Gameroom
1 3
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.
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 46 reviews
Winter Haven, FL
02/07 – 06/07
643 €/nighttotal: 2572 € (4 )
Costa 5bd Lego Themed Pool Home | Your Own 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.
10 18 reviews
Winter Haven, FL
17/07 – 24/07
88 €/nighttotal: 616 € (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.
9.4 89 reviews
Winter Haven, FL
14/07 – 11/08
96 €/nighttotal: 2688 € (28 )
Stylish-n-private 1br Retreat 2 Miles To Legoland
1 2
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.
9.6 413 reviews
Winter Haven, FL
07/07 – 12/07
142 €/nighttotal: 710 € (5 )
★3/2★spacious-lakehome☀aceloc☀4miles🎢legoland🎢
3 4
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.
Best Winter Haven, FL holiday rentals with parking
8.0 1 review
Winter Haven, FL
02/07 – 06/07
478 €/nighttotal: 1912 € (4 )
Ultimate Family Getaway: 4br Home With Pool & Games
4 9
apartment , Winter Haven
This spacious five-bedroom dwelling in Winter Haven is conveniently located approximately 5 kilometres from Legoland and offers easy access to Downtown Winter Haven and the Central Florida lakes. This family-friendly apartment accommodates up to ten guests and features a private swimming pool, a fenced yard, a pool table, and a semi-private suite with its own kitchenette, making it ideal for a holiday rental.
9.4 29 reviews
Winter Haven, FL
27/06 – 04/07
160 €/nighttotal: 1120 € (7 )
Game Room And 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.
10 3 reviews
Winter Haven, FL
27/06 – 04/07
168 €/nighttotal: 1176 € (7 )
Best Sunsets In Winter Haven. Lakefront Home 5 Minutes From Downtown!
2 2
apartment , Winter Haven
This Winter Haven holiday home is conveniently located approximately 2 kilometres from Rotary Park, offering easy access to Winter Haven Hospital and Winter Haven Women's Hospital (within 5 kilometres), and Lake Conine and Indigo's Family Fun Centre (also within 5 kilometres). The two-bedroom, two-bathroom property sleeps four guests and boasts a fully equipped kitchen, patio, smart TV, and parking; enjoy nearby recreational activities at Rotary Park or family fun at Lake Conine and Indigo's Family Fun Centre.
10 8 reviews
Winter Haven, FL
08/07 – 12/07
180 €/nighttotal: 720 € (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?
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?
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?
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?
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.
Destinations nearby
Best Winter Haven, FL holiday rentals with a balcony
Winter Haven, FL
14/07 – 11/08
186 €/nighttotal: 5208 € (28 )
Golf, Dine And Unwind Poolside! Haines City Getaway
1 2
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.
Winter Haven, FL
27/06 – 04/07
93 €/nighttotal: 651 € (7 )
Cozy 1br Minutes From Legoland & Downtown Winter Haven
1 2
apartment , Cypress Gardens
This Winter Haven flat is located 2.9 kilometres from LEGOLAND Florida and 10.9 kilometres from Swanns Railroad Station. This 93 square metre apartment, suitable for up to 7 guests, offers free Wi-Fi, air conditioning, a fully equipped kitchen, and a terrace, with complimentary private parking and car rental available on-site.
10 2 reviews
Winter Haven, FL
14/07 – 11/08
89 €/nighttotal: 2492 € (28 )
Winter Haven Apt: 1 Mi To Polk State College!
1 2
apartment , Winter Haven
This Winter Haven apartment is conveniently located within 1.6km of Rotary Park and Winter Haven Hospital, and within 4.8km of Winter Haven Women's Hospital and Indigo's Family Fun Centre. The self-catering flat offers free Wi-Fi, parking, a private balcony, and is close to various amenities including a hospital and family entertainment.
8.5 31 reviews
Winter Haven, FL
07/07 – 12/07
107 €/nighttotal: 535 € (5 )
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.
Best Winter Haven, FL holiday rentals with air conditioning
8.6 26 reviews
Winter Haven, FL
07/07 – 12/07
127 €/nighttotal: 635 € (5 )
Luxury Staycomfy At Winterheaven
2 4
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.
9.9 74 reviews
Winter Haven, FL
16/07 – 20/07
122 €/nighttotal: 488 € (4 )
Legoland On The Lake
1 2
house , Winter Haven
This Winter Haven apartment is ideally situated, 5.8km from Legoland Florida, 21km from Bok Tower Gardens, and 9.6km from Winter Haven's town centre and its restaurants. The self-catering property sleeps four guests in one bedroom and one bathroom, boasting a lake-view garden, fire pit, and keyless entry; nearby attractions include Disney World parks (48km away).
9.9 20 reviews
Winter Haven, FL
14/07 – 11/08
87 €/nighttotal: 2436 € (28 )
Cozy Castle
1 2
apartment , Winter Haven
This Spanish Gothic property, a century-old residence, is centrally located in Winter Haven, providing easy access to LEGOLAND (approximately 5 kilometres away), Bok Tower Gardens (around 10 kilometres away), and Florida Southern College. This two-bedroom flat accommodates up to six guests and features a kitchen, air conditioning, and parking, offering modern comforts within a historic setting with proximity to the Chain-of-Lakes for water activities.
10 20 reviews
Winter Haven, FL
14/07 – 11/08
49 €/nighttotal: 1372 € (28 )
Charming Boutique Apt/quiet Stay/ Near Lakes &Dw
1 2
house , Winter Haven
Cozy Vintage, a one-bedroom apartment in a peaceful Winter Haven neighbourhood, is minutes from restaurants, shops, hospitals, and a lake ideal for fishing and relaxation. Apartment D, sleeping three guests, offers a full kitchen (fridge, freezer, microwave), bathroom, and a sofa bed, with shared BBQ, patio, and parking available at this beautifully restored two-story property.
