Holiday Rentals in Winter Haven, FL

This modern 4-bedroom detached house in Winter Haven is conveniently located a short distance from the city centre and 24 kilometres from Legoland, making it ideal for families and groups.
This spacious property accommodates up to 10 guests and features a private swimming pool, a pool table, a fully equipped kitchen with a mini bar, and high-speed Wi-Fi, ensuring a comfortable and entertaining stay.

This lakeside property near Eagle Lake offers three bedrooms, two bathrooms, and sleeps eight, boasting stunning lake views and proximity to Legoland Florida Resort, although precise distances aren't specified.
The self-catering holiday home includes a fully equipped kitchen with dishwasher, a private hot tub, a game room with pool table, table tennis and darts, and ample parking including a two-car garage.

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.

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.

This apartment is located in Winter Haven, a short drive from both Theatre Winter Haven and the Water Ski Museum and Hall of Fame, making it a convenient base for exploring the area. It has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This spacious property offers four bedrooms and three bathrooms, comfortably accommodating up to eleven guests. It boasts a private pool, screened-in lanai, a well-equipped kitchen, a playroom, and a soundproofed ensuite bedroom, ensuring a comfortable and enjoyable stay for families and groups.

This Winter Haven flat is located 1.6 kilometres from Polk State College and is within walking distance of the city centre, with Disney's Animal Kingdom Theme Park and Disney's Hollywood Studios a short drive away.
This pet-friendly apartment accommodates two guests, offering complimentary Wi-Fi, air conditioning, a kitchen, a terrace, and free parking, with contactless check-in and check-out available for convenience.

This two-bedroom house is located in Winter Haven, just 1.3 kilometres from Baytree Golf Club and 2.6 kilometres from LEGOLAND® Florida. It has consistently received excellent reviews from previous guests.
The property can accommodate up to five guests and comes equipped with a fully equipped kitchen, free Wi-Fi, and air conditioning. You can enjoy a range of activities nearby, including golfing, exploring the Chain of Lakes, or visiting the popular theme parks.

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.

This Haines City holiday home is located within the prestigious Southern Dunes Golf & Country Club community, approximately 1.6km from a Walmart Supercentre and various restaurants, and a 32-48km drive from major theme parks such as Walt Disney World Resort and Legoland Florida.
The three-bedroom property, sleeping up to six guests, boasts a private pool with a cage and alarm, offering waterfront views, alongside access to resort amenities including tennis courts, a children's play area, and a clubhouse with a restaurant and bar; a fully equipped kitchen with granite worktops and stainless-steel appliances is also included.

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.

This updated villa is located in the Southern Dunes area of Haines City, offering direct golf course views.
The property spans 143 square meters and features a kitchen with a fridge, microwave oven, and dishwasher, alongside air conditioning, a swimming pool, terrace/balcony, and on-site parking.

This three-bedroom apartment is located in Haines City, Florida, just 2.2 kilometres from Southern Dunes Golf Club and Southern Dunes Golf and Country Club. The apartment provides a comfortable and relaxing setting for a family holiday.
The property has two bathrooms and can accommodate up to six guests. Enjoy the convenience of a fully equipped kitchen, a private balcony, a shared swimming pool, and on-site parking.

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.

This two-bedroom, two-bathroom apartment in a gated Winter Haven community is located minutes (approximately 1-2 km) from LEGOLAND Florida and close to other attractions such as Theatre Winter Haven and Chain of Lakes Park.
The 119 square metre property offers a spacious layout sleeping up to six guests, boasting a fully equipped kitchen, in-unit laundry, smart TVs, a private garden, and access to resort-style amenities including a heated pool, fitness centre, and tennis court.

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.

This charming cottage is situated on a private canal leading to Lake Eloise, just a short distance from Cypress Gardens, Legoland and Disney World, making it ideal for families looking to explore the area. It has consistently received excellent ratings for its cleanliness, location and overall experience.
The cottage has one bedroom and one bathroom, comfortably accommodating up to four guests. The property features a fully equipped kitchen, air conditioning, a garden and private canal access for fishing, as well as a white noise machine for a peaceful night's sleep.