Holiday Rentals in Winter Haven, FL

This spacious Winter Haven apartment, ideal for large groups, enjoys a waterfront location in a central Orlando neighbourhood, less than 80 kilometres from Walt Disney World.
Sleeping up to twelve guests in five queen beds and one bunk bed, the property boasts a fully equipped kitchen, private pool, game room, and is within easy reach of local shops, restaurants, and parks.

This spacious four-bedroom house in Winter Haven, Florida, is ideally located 18km from Legoland Florida Resort and within a 32km radius of other attractions including Disney World and Universal Studios.
The 4-bedroom, 2-bathroom property sleeps up to 10 guests and boasts a large garden with covered patio, full kitchen with dishwasher, air conditioning, Wi-Fi, and ample parking; professional pest control is also provided.

This expansive two-home property in Winter Haven is located just three houses from Lake Howard, offering direct access to the Chain of Lakes trail and boat docks, with Legoland and various sports venues within a 15-minute drive.
This pet- and family-friendly residence accommodates up to 16 guests with six bedrooms and three bathrooms, featuring a fully stocked kitchen, air conditioning, a fenced garden, and ample parking for four vehicles, including two covered spaces.

This fully renovated 1940s lake house is situated just a short drive from Winter Haven's charming downtown area, with its restaurants and shops, and within 10 minutes of Legoland. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious home can comfortably accommodate up to 10 guests in its four bedrooms and four bathrooms. The apartment offers a range of amenities for a comfortable stay, including a large kitchen, a dedicated games room, a swimming pool, and a spa.

This glamping experience is located at Cypress Inlet, within Cypress Gardens, adjacent to a road intersection, offering a genuine camper experience with some ambient road noise.
This fully furnished RV camper sleeps up to four guests and features air conditioning, a fridge, microwave oven, a stove, a stand-up shower, and a camper-style toilet, with pets and internet also permitted.

This three-bedroom home is located in Winter Haven, Florida, just 15 kilometres from LEGOLAND and Peppa Pig Theme Park, and within a 10-kilometre drive of shops, restaurants, and parks. The apartment is perfect for families, with a fully fenced garden and a capacity for up to eight guests.
The apartment is equipped with a modern kitchen, a 55-inch Smart TV with Netflix and Hulu, and a washer and dryer, as well as a keyless entry system for convenient check-in and check-out. Guests can also enjoy the fully fenced garden, perfect for relaxing or playing games.

This five-bedroom flat in Cypress Gardens offers serene waterfront living on Lake Florence, located just a few minutes from LEGOLAND Florida and the shops and dining of downtown Winter Haven.
This property comfortably accommodates up to 12 guests and features a private outdoor heated swimming pool, a balcony with BBQ facilities, and a dedicated games room, all within easy reach of local attractions.

This three-bedroom property is located in Winter Haven, Florida, just a short drive from Legoland and within easy reach of Orlando's main attractions. The apartment has received excellent reviews from previous guests.
This comfortable home can accommodate up to seven guests and features a well-equipped kitchen, air conditioning, a garden, parking, and internet access. Guests can enjoy a peaceful lakeside setting with direct access to water activities, or explore the nearby natural areas and local attractions.

This lakeside property in Winter Haven, Florida, is situated on Lake Otis, 7.2 kilometres from Legoland Florida and Peppa Pig Theme Park, and 45 kilometres from the Walt Disney World Resort.
This 439-square-metre house boasts four bedrooms, five bathrooms, sleeps ten guests, and includes a heated pool, a pontoon boat package, and a games room, all within easy reach of Publix and Winter Haven's town centre.

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.

This Haines City holiday home boasts a superb location, approximately 24 kilometres from Legoland Florida and 32 kilometres from both Disney's Blizzard Beach and Disney's Wide World of Sports.
This four-bedroom, three-bathroom property offers 161 square metres of living space, complete with a private pool, lanai, fully equipped kitchen, and free Wi-Fi, comfortably accommodating larger families or groups.

This three-bedroom, two-bathroom house is situated 3.5 km from Legoland Florida, offering easy access to both Lakeland and Orlando airports and convenient proximity to Cypress Gardens.
The property sleeps eight guests and boasts a private pool, two family rooms, indoor/outdoor dining areas, multiple large TVs, a fully equipped kitchen with a dishwasher, laundry facilities, and Wi-Fi; nearby attractions include Cypresswood Golf and Country Club and the KICCO Wildlife Management Area.

This four-bedroom lakefront property in Winter Haven, Florida, is located 10.3 km from Legoland Florida and within 16 km of several historic railway stations.
This spacious 307-square-metre holiday home boasts a fully equipped kitchen, a jacuzzi, free Wi-Fi, and comfortably accommodates up to 43 guests, offering a fireplace and washing machine for added convenience.

This apartment is located in the Park Lake district of Winter Haven, just a short walk from restaurants and next to the Winter Haven Fieldhouse and Chain O Lakes Park, providing easy access to outdoor activities and attractions. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment has two bedrooms and bathrooms, comfortably accommodating up to two guests. It comes with a well-equipped kitchen, air conditioning, parking, internet access, and welcomes pets, making it an ideal choice for a comfortable and convenient stay in Winter Haven.

This pet-friendly Winter Haven lodge is conveniently located near restaurants (8 km) and Legoland Florida (16 km), with Winter Haven's Antrak station a mere 2.4 km walk away.
The self-catering cottage offers keyless entry, a private yard with a dog house, one bedroom, one bathroom, sleeps two guests, and includes amenities such as free coffee, bathrobes, and a water filter.

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.