Compare vacation rentals in Winter Haven from 100+ sites!

This lake-life inspired cottage, centrally located in Winter Haven, is within walking distance of downtown entertainment and a short drive to Legoland, Tampa, and Orlando. The cottage has excellent user, location, and cleanliness ratings.
With 2 bedrooms and 1 bathroom, the cottage can accommodate up to 8 guests. It has a well-stocked kitchen, a backyard with board and bean toss games, propane and charcoal grills, and amenities such as a foosball table, washer & dryer, and a baby crib and high chair upon request.

This lakefront Cabana is located in a quiet neighborhood in Winter Haven, offering privacy and direct access to Lake Eloise. It has excellent user, location, and cleanliness ratings.
The Cabana has one bedroom, one bathroom, and can accommodate up to four guests. It has a floor area of 400 square feet. The Cabana has a private dock, a spacious outdoor area, and access to a shared pool. It also has air conditioning, a kitchen, a microwave oven, a fridge, and a spa.

This private house is located in Winter Haven, Florida, offering easy access to nearby attractions. It has received excellent ratings for its location, cleanliness, and amenities.
The house has one bedroom and one bathroom and can accommodate up to three guests. It features a spacious backyard with a grill, dining area, corn hole tables, hammocks, and a fire pit. The house also has a covered parking space and a fenced-in backyard.

The Flamingo is a 3-bedroom, 2-bathroom accommodation in Winter Haven, Florida. It has an excellent user rating and is conveniently located 5 miles from Legoland and 30 miles from Disney World.
The Flamingo has a spacious layout with an open living room, dining room, and kitchen area. It also has a back porch and yard with trees. The accommodation is allergy-friendly, smoke-free, and has a laundry room available for guest use.

This pet-friendly cabin in Haines City is perfect for a family vacation. It has a fully equipped kitchen, air conditioning, and a garden. The cabin is also close to many popular attractions, including Legoland Florida and Disney World.
The cabin has received excellent ratings from previous guests, who praise its cleanliness, location, and amenities. It has one bedroom and one bathroom and can accommodate up to four guests. The cabin also has a fully equipped kitchen, a living room with a TV, and a private patio.

This 3-bedroom, 2-bathroom apartment is part of a duplex located on 2.6 acres of lakefront property in Winter Haven, just 4 miles from LEGOLAND. With excellent user ratings, this apartment is an ideal choice for families or groups of up to 7 people.
The apartment features a fully equipped kitchen, a living area, and a private patio or balcony overlooking the lake. Guests can enjoy access to a private Tiny Home on the same grounds, as well as amenities such as air conditioning, internet, and parking. Nearby attractions include LEGOLAND, SeaWorld, Disney, Universal, and Downtown Orlando, making it an excellent base for exploring the area.

This apartment is located in the heart of Winter Haven, within a 15-minute walk of Inman Park and Lake Conine. It has excellent user, location, and cleanliness ratings.
The apartment has 1 bedroom, 1 bathroom, and a guest capacity of 3. It features a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a terrace/balcony, a garden, and parking. The apartment also offers free WiFi, a sofa bed, a patio, and is in a smoke-free environment.

This studio, located in Winter Haven, offers a private dock on 3 acres of lakefront property, just 4 miles from LEGOLAND and an hour's drive from popular Orlando attractions like Disney World and SeaWorld. With excellent user, location, and cleanliness ratings, this studio is a top choice for travelers visiting Winter Haven.
The spacious studio accommodates up to 3 guests with two lofted beds (King and Twin) and features a fully equipped kitchen, free Wi-Fi, 55" Roku TV with streaming services, and a washer and dryer. Guests can also enjoy the garden, parking, and outdoor surveillance for added security.

This apartment in Winter Haven is family friendly and has an excellent user rating. It is conveniently located near popular landmarks and offers a peaceful ambiance.
The apartment has one bedroom, one bathroom, and can accommodate up to three guests. It features a fully equipped kitchen, air conditioning, a garden, parking, and free Wi-Fi. Guests can enjoy activities such as swimming, fishing, and biking in the nearby area.

This lakeside cottage in Winter Haven offers a tranquil escape with stunning lake views. Just 3 miles from Rotary Park, Baytree Golf Club, and Winter Haven Hospital, this highly-rated cottage provides a convenient base for exploring the city's attractions.
Inside, the cottage features a fully equipped kitchen, modern amenities like a Smart TV and internet access, and a spacious layout with 2 bedrooms and 1 bathroom, accommodating up to 3 guests. Guests can enjoy the outdoor terrace or balcony, and take advantage of the pet-friendly policy and air conditioning for a comfortable stay.

This apartment is conveniently located in the heart of Winter Haven, within walking distance of Inman Park and Lake Conine, and within 3 miles of Winter Haven Hospital and Rotary Park. With an excellent user rating, this one-bedroom, one-bathroom apartment can accommodate up to three guests.
The apartment features a fully equipped kitchen with a refrigerator, stovetop, and microwave, a sofa bed for additional sleeping arrangements, a private balcony, and complimentary WiFi. Guests can also enjoy access to a water park, a garden, barbecue grills, a swimming pool, a spa, and parking.

This waterfront vacation home is situated in Winter Haven, offering easy access to popular theme parks and attractions within a short driving distance. It has received excellent user ratings.
The apartment has a floor area of 2300 square feet and can accommodate up to 10 guests. It has 4 bedrooms and 3 bathrooms. The amenities include a fully equipped kitchen, a heated pool, a hot tub, a private pier with water sports, and a spacious terrace with a garden.

Located in a quiet neighborhood within walking distance of Southern Dunes Golf Club, this highly-rated vacation home offers a peaceful retreat for travelers visiting Haines City. With a user rating of "excellent," this 1500-square-foot, 3-bedroom home provides ample space for families or groups.
The vacation home features a fully equipped kitchen, a DVD player, a dining area, and a sitting area. Guests can enjoy amenities such as a swimming pool, a terrace/balcony, a garden, a spa, a concierge, a restaurant, a fitness center, a tennis court, and parking.

Balmoral Resort Florida is a family-friendly hotel located in Haines City, Florida, just 2.7 miles from Southern Dunes Golf Club. The resort has received very good ratings for its location, cleanliness, and user experience.
The resort offers a range of amenities and activities, including an outdoor pool, fitness center, bar/lounge, poolside bar, and free self-parking. Guests can also enjoy free water park access and limited housekeeping services. The resort's spacious rooms and suites feature air conditioning, a private balcony or terrace, and room service.

This 4-bedroom vacation rental home is located in the exclusive Southern Dunes Golf and Country Club, a gated community in Haines City, Florida, with a secluded tropical setting overlooking the 7th fairway of the award-winning Southern Dunes Golf Course. It has excellent user, location and cleanliness ratings.
The home has stylish all-ceramic flooring throughout, and modern amenities like high-speed internet, cable TV, Roku TVs, keyless entry, smart thermostat, motion sensors, door sensors, and a smart home monitor. It can accommodate up to 8 guests and has a private pool with stunning golf course views. Guests also have access to community amenities within Southern Dunes Golf and Country Club, including a children's playground, 3 community pools, a tennis court, a fitness center, and a country club with a bar and restaurant.

This family-friendly villa is located within walking distance of Southern Dunes Golf Club and Southern Dunes Golf and Country Club in Haines City. The property offers 2050 square feet of living space with 4 bedrooms and 2 bathrooms.
Guests can enjoy amenities such as free WiFi, a washing machine, a tennis court, a swimming pool, a fitness center, a restaurant, a terrace, a garden, and a smoke-free environment. The villa also provides free self-parking and cable TV.

This villa is located in Haines City, within 1 mile of Southern Dunes Golf Club and 9 miles of Lewis W Mathews Memorial Sports Complex. This house has excellent user ratings.
This 1990 square feet house has 4 bedrooms and 3 bathrooms. It features a private pool, free WiFi, a kitchen, 3 bathrooms, a washer/dryer, a dining area, a TV, a water park, a spa tub, an arcade/game room, and barbecue grills.

This Haines City vacation home is conveniently located near major tourist attractions, including Southern Dunes Golf Club, Southern Dunes Golf and Country Club, Lake Henry Golf Club, and True Blue Winery. The home has received very good user ratings and an excellent location rating.
The spacious 1820-square-foot home features 3 bedrooms and offers a private pool, fitness center, arcade/game room, patio, and a kitchen with essential appliances. Guests can enjoy a smoke-free environment and proximity to nearby attractions.

This condo is located in Haines City, within walking distance of Wal-Mart and other amenities, and a short drive from LEGOLAND® Florida. It has an excellent user rating.
The privately owned and maintained condo is located on the second floor of a 2-storey building and has a balcony. It has 2 bedrooms, 2 bathrooms, and can accommodate up to 8 guests. It features a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a communal pool, a sunbathing area, a golf club, on-site parking, and 24-hour security.

This 4-bedroom vacation home is located in Haines City, within walking distance of Southern Dunes Golf Club, and a short drive from True Blue Winery and Lewis W Mathews Memorial Sports Complex. With very good user ratings, this house has 2 bathrooms, a kitchen with a refrigerator and microwave, a washing machine, and a dining area.
It also offers amenities such as a private pool, free parking, internet access, and a smoke-free environment.

This charming 1908 apartment lies in the heart of Winter Haven, within walking distance of downtown and Lake Howard. It's also just a short drive from Legoland and Chain O'Lakes.
The apartment has received excellent ratings for its cleanliness, location, and user experience. It features 4 bedrooms, 2 bathrooms, a fully equipped kitchen, a living room, a porch, and a backyard. It can accommodate up to 9 guests and offers amenities such as air conditioning, a fitness center, parking, and a garden.

This 3-bedroom apartment is located on a private 3-acre lakefront property just 2 miles from downtown Winter Haven and 4 miles from LEGOLAND. It has excellent user, location, and cleanliness ratings.
The apartment has 2 full bathrooms and can accommodate up to 7 guests. It features a fully equipped kitchen, a laundry room, and a private porch and yard. Guests can enjoy complimentary Wi-Fi, Roku Smart TVs with streaming services, and access to outdoor amenities like designated parking and a garden.

Roe Family Lakehouse, a family-friendly cottage on Eagle Lake, is surrounded by mature trees, a spacious garden, and a private boat launch. Just 10 minutes from Legoland and less than an hour from Tampa or Disney World, it's the perfect base for exploring the area.
With excellent user, location, and cleanliness ratings, this two-bedroom, one-bathroom cottage accommodates up to five guests. It features a fully equipped kitchen, air conditioning, Wi-Fi, and a detached garage for extra space. Guests can enjoy fresh fruit from the property's fruit trees, relax in the garden, or take advantage of the public boat launch for water sports and fishing.

Located in the heart of Winter Haven, this family-friendly apartment is within walking distance of downtown and a half mile from dining and shopping, and only 15 minutes from Legoland. With excellent user, location, and cleanliness ratings, this 3-bedroom, 1-bathroom apartment comfortably accommodates up to 8 guests.
The apartment features a fully stocked kitchen, air conditioning, a private patio, and a cozy outdoor space, as well as amenities like games, puzzles, and DVDs for entertainment. It also provides a workspace for guests who need to work or study, and grilling facilities for outdoor cooking.

Located within a 15-minute walk from Inman Park and Lake Conine, this one-bedroom, one-bathroom apartment in Winter Haven has received excellent user ratings. It accommodates up to two guests and features a patio by the sea, free WiFi, a kitchen with essential appliances, and a washing machine.
The smoke-free building offers a garden with barbecue grills, air conditioning, and parking. Other amenities include a dining table, coffee/tea maker, and access to a terrace or balcony.

This 1-bedroom apartment is perfect for those looking for a winter getaway to Winter Haven. With its convenient location, excellent ratings, air conditioning, and a fully equipped kitchen, you'll have everything you need for a comfortable stay.
The apartment is also family-friendly and has a garden, making it a great choice for those traveling with children. Plus, with internet access, you can stay connected with friends and family back home.

This cozy studio in Winter Haven is minutes from the historic downtown and convenient for exploring Legoland Florida (15 min) and Bok Tower Gardens (20 min). It enjoys excellent user ratings for location, cleanliness, and comfort.
The studio features a cozy modern vintage design with a kitchenette, private bathroom, and comfortable seating area. It’s perfect for couples looking for a cozy and intimate getaway. Guests can enjoy outdoor dining and grilling in the shared common space.

This Winter Haven vacation home is conveniently located in the heart of the city, within easy walking distance of Winter Haven Hospital (0.5 miles) and Rotary Park (0.8 miles). The house has earned excellent ratings for its location, cleanliness, and user experience.
The house features 5 bedrooms and 3700 square feet of floor area, making it ideal for families or groups. It offers a fully equipped kitchen, a shared bathroom, free Wi-Fi, a DVD player, and housekeeping available on request. Guests can also enjoy a terrace/balcony, a garden, a tennis court, and parking.

Eagle Lake offers a unique accommodation, Victorian Loft, surrounded by 35 acres of organic lemon groves, only 5 miles from LEGOLAND*Florida. It has excellent user, location, and cleanliness ratings.
This one-bedroom, one-bathroom treehouse has a private entrance and accommodates two guests. It features a kitchen, air conditioning, a swimming pool, a garden, parking, and allows pets. Guests can enjoy gardening, use the outdoor hot shower, and relax by the lakeside pool.

This apartment is conveniently located in Winter Haven, within a 5-km radius of key attractions such as Rotary Park, Baytree Golf Club, and Winter Haven Hospital. It has excellent user, location, and cleanliness ratings.
The apartment features a comfortable layout with one bedroom, one bathroom, and a well-equipped kitchen. It also includes amenities such as air conditioning, a garden, parking, and internet access. Guests can enjoy the convenience of a private entrance and a sofa bed for additional sleeping arrangements.

This smoke-free vacation home is located on a lake, 1.5 miles from Lions Park and within 6 miles of Lake Henry Golf Club and Inman Park. It has excellent user, location, and cleanliness ratings.
The house has 3 bedrooms, 2 bathrooms, and a floor area of 1600 square feet. It can accommodate up to 6 guests. It features a fully equipped kitchen, air conditioning, a terrace/balcony, a garden, and parking. Guests can enjoy stunning lake views, a private yard, and free WiFi.

This apartment is conveniently located within 3 miles of major landmarks in Winter Haven, making it an ideal choice for travelers seeking a comfortable and convenient stay in the area. With a very good user rating, this apartment offers a comfortable and enjoyable experience for guests.
The apartment features a well-equipped kitchen, a comfortable living area with a sofa bed and Smart TV, and modern amenities such as free WiFi and a Smart TV. It also includes convenient amenities such as parking and in-unit laundry facilities, making it a great option for families and those seeking a hassle-free stay.

This waterfront vacation home in Winter Haven offers stunning views and easy access to water activities. It's within walking distance of Lake Conine and Inman Park, and a short drive from Winter Haven Hospital and Rotary Park. With excellent user ratings for location, cleanliness, and amenities, this house is a great choice for families or groups.
The house has 3 bedrooms, a sofa bed, and a patio, providing ample space for up to 8 guests. It features a well-equipped kitchen, a fireplace, and a private garden with barbecue grills. The house is also pet-friendly and offers free Wi-Fi.

This apartment offers a unique stay on Lake Roy, part of the Winter Haven Chain O' Lakes, with direct access to Cypress Gardens Adventure Park. Guests have rated this apartment as excellent in terms of location, cleanliness, and user experience. The apartment features two bedrooms, 1.5 bathrooms, a full kitchen, and a living room with a pool table, accommodating up to 5 guests. Aside from the spacious layout, guests will enjoy amenities like a private entrance, keyless touchpad, outdoor shower and tub, water activities, and boat rental and parking.

This vacation home in Winter Haven is conveniently located near Sertoma Park, Indigo's Billiards, Bowling & Games, and Theatre Winter Haven. It has received excellent user ratings, making it a top choice for travelers.
The house features 4 bedrooms and 2 bathrooms, accommodating up to 10 guests comfortably. It includes a fully equipped kitchen, air conditioning, a swimming pool, a terrace/balcony, a garden, parking, and free WiFi. Guests can also enjoy access to a water park, barbecue grills, and a fenced private yard.