Compare temporary rentals in Winter Haven from 100+ providers!

This vintage apartment is located in a quiet residential area of Winter Haven, 1 mile from downtown, 4.3 miles from LEGOLAND Florida, and 2.5 miles from Chain of Lakes Park.
This one-bedroom, one-bathroom rental sleeps up to three guests and features a kitchenette with a fridge, freezer, and microwave, plus air conditioning, internet, a shared garden, and parking.

This 2-bedroom, 2-bathroom condo in central Winter Haven offers convenient access to the chain of lakes, Legoland Florida Resort, and downtown amenities, providing a local experience for exploring Central Florida.
This private residence accommodates up to 4 guests with a kitchen, air conditioning, garden, and parking, perfect for enjoying Bok Tower Gardens and nearby attractions.

This lakeside Winter Haven vacation home is situated near Indigo's Family Fun Center and Winter Haven Hospital, a short drive from Rotary Park and a 25-minute walk from Winter Haven Station.
This 1800-square-foot property boasts four bedrooms, two bathrooms, and accommodates up to nine guests, featuring a fully equipped kitchen, fitness center, terrace, and a tranquil lakeside setting ideal for water activities.

This historic B&B is in the heart of downtown Winter Haven's historic district, with restaurants, shops, and bars within walking distance. It has excellent user and location ratings.
The restored 1910 rooming house has one bedroom with a private bathroom and access to multiple shared bathrooms, a kitchen, a dining room, a living room, and a wrap-around porch with rocking chairs. The room has a small refrigerator, and there is free parking.

This Winter Haven lakeside cottage, a short 15-minute walk from Winter Haven Women's Hospital and less than a mile from Indigo's Family Fun Center and Rotary Park, offers convenient access to downtown attractions and family entertainment.
This 710-square-foot house features two bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, in-unit laundry, a terrace, and barbecue grills.

This five-bedroom, three-bathroom Winter Haven vacation home is located near Cypress Gardens, within three miles of Baytree Golf Club and LEGOLAND Florida.
The property boasts a private pool, a terrace, a fully equipped kitchen including a refrigerator, microwave, and dishwasher, free WiFi, and accommodates up to six guests, perfect for families visiting the area's attractions.

This Winter Haven vacation home is minutes from Legoland Florida, Chain of Lakes Park, and historic downtown Winter Haven.
The three-bedroom house, sleeping eight with a pull-out sofa bed, features a fully equipped kitchen, fast Wi-Fi, fenced yard, and convenient keypad entry.

This Haines City vacation home is conveniently located within a 15-minute walk of Southern Dunes Golf Club and Southern Dunes Golf and Country Club, and within 6 miles of True Blue Winery. This property has received very good user ratings, making it a popular choice for travelers.
The house offers a comfortable and spacious layout, with 1550 square feet of living space and a guest capacity of 8. Enjoy the private pool, the well-equipped kitchen, the three bathrooms, the tennis courts, and the internet access.

This lakefront home on Lake Howard in Winter Haven offers stunning water views and is a short drive from LEGOLAND and walkable downtown.
This 4-bedroom, 3-bathroom house accommodates 8 guests and features a heated saltwater pool, hot tub, private dock on Lake Howard, and water views from nearly every room.

This lakefront house on Lake Howard in Winter Haven offers 2200 square feet of living space with 4 bedrooms, 3 bathrooms, and a guest capacity of 8, featuring a heated saltwater pool, hot tub, and a private dock for fishing. Located just 5 miles from downtown Winter Haven and 10-12 miles from LEGOLAND Florida, this rental provides convenient access to local dining, shops, and central Florida attractions.

This Winter Haven vacation rental is conveniently located just 5 miles from Legoland, 23 miles from Disney World, and 35 miles from Universal Studios, making it an ideal base for exploring Central Florida's attractions. The property has received excellent user ratings, indicating a comfortable and enjoyable experience for guests.
This spacious 4-bedroom, 3-bathroom home comfortably accommodates up to 10 guests with a total floor area of 2300 square feet. Enjoy a private pool and hot tub, direct waterfront access to Lake Hamilton, a fully equipped kitchen, and convenient amenities like a laundry room and parking.

This 4-bedroom lakefront home is located in Eagle Lake, Florida, just a short drive from LEGOLAND® Florida and major theme parks like Disney, Universal Studios, and SeaWorld. The property has earned a "very good" user rating, indicating a positive experience for previous guests.
This spacious vacation rental offers 2,800 square feet of living space, comfortably accommodating up to 12 guests. It features a private pool and jacuzzi, a game room with entertainment options, a boat dock, and a lakefront balcony with stunning views.

This charming cottage is situated on a lake in Winter Haven, just a short distance from Rotary Park, Baytree Golf Club, and several hospitals. Travelers will appreciate the cottage's excellent ratings and its proximity to popular attractions.
The cozy cabin offers two bedrooms and one bathroom, comfortably accommodating up to three guests. Enjoy modern amenities, a fully equipped kitchen, a terrace, and internet access, making it perfect for a relaxing getaway.