Best Short term and Weekly rentals in Winter Haven

About: This apartment is located in Southern Dunes Golf & Country Club, minutes from golf courses, theme parks, and shopping. It is surrounded by lush greenery and has a secluded tropical ambiance.

The apartment has excellent user, location, and cleanliness ratings.

It has 4 bedrooms, 3 bathrooms, and a floor area of 1550 square feet, accommodating up to 8 guests.

This apartment offers a private pool with a lounge area and BBQ grille, award-winning golf course and amenities, spacious accommodations, and modern Scandinavian design with high-quality materials and appliances.

About: This cottage is located in Cypress Inlet Vacation Homes and Marina, near Legoland, Advent Field House, and Lake Eloise. It offers a peaceful ambiance with direct canal access to Lake Eloise and proximity to major attractions.

With excellent user, location, and cleanliness ratings, this cottage offers a comfortable stay.

The cottage features a modern interior design with a covered front porch and a layout that includes 3 Smart TVs with YouTube TV, free WiFi, a kitchen with a fridge, freezer, microwave oven, and dishwasher, and air conditioning.

Guests can enjoy nearby activities such as visiting Legoland, Disney World, and Universal Orlando Resort, or simply relax in the garden or fitness center.

About: Centrally located in Winter Haven, within walking distance of downtown entertainment and a short drive from Legoland (5.2 miles), this family-friendly cottage offers a unique and appealing experience for guests.

With excellent user, location, and cleanliness ratings, this 2-bedroom, 1-bathroom cottage accommodates up to 8 guests. It features a well-stocked kitchen with washer & dryer, a fooseball table, board games, puzzles, and DVDs, backyard board and bean toss games, and propane and charcoal grills with grilling utensils. A baby crib and high chair are available upon request.

About: This apartment is located in a gated community in southern Winter Haven, adjacent to Legoland. It offers sunsets over Round Lake and is a short drive from the city center.

The apartment has excellent ratings for its location, cleanliness, and amenities. It has 3 bedrooms, 2 bathrooms, and can accommodate up to 6 guests.

The apartment features a saltwater pool with a screened enclosure, a fully equipped kitchen, air conditioning, and Smart TVs in every room. Guests can enjoy the open floor plan and comfortable space, as well as the proximity to Legoland and other attractions.

About: Located in a quiet neighborhood near Legoland (3 minutes) and Disney (35 minutes), this B&B offers a peaceful ambiance for your stay in Cypress Gardens. It has excellent user, location, and cleanliness ratings.

The B&B features a private bedroom with a queen bed and a pull-out bed for 4, a private bathroom, and a private screened patio with seating. Amenities include a swimming pool (open from 9 AM to 8 PM), a mini-fridge, a coffee maker, complementary snacks, a hair dryer, and pool towels. Free Wi-Fi is also available.

About: This B&B is in the heart of historic downtown Winter Haven, within walking distance of bars, restaurants, shops, and entertainment. The ambiance is historic, as the building is an original 1910 rooming house.

The B&B has excellent user, location, and cleanliness ratings.

It has 1 bedroom and 3 bathrooms, and can accommodate 2 guests.

Amenities include a shared kitchen, dining room, and living room, a wrap-around porch with rocking chairs, a small fridge in the room, air conditioning, a garden, parking, and Wi-Fi.

About: This cottage is situated on a private canal in Cypress Gardens, near Legoland and Disney World, in a peaceful and quiet area. It has excellent user, location, and cleanliness ratings.

It has 1 bedroom, 1 bathroom, and can accommodate up to 4 guests.

It features a fully equipped kitchen, a cozy and comfortable interior, an outdoor area with seating and grill, a "white noise" machine for noise reduction, and private canal access to Lake Eloise for fishing.

About: This apartment is located in Winter Haven, directly across from Lake Howard boat ramp, 10 minutes from Legoland. It has excellent user, location, and cleanliness ratings.

The mid-century modern home has 3 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. It has a spacious 2300 sq ft layout and is fully furnished with new furnishings, bedding, and towels.

It has a fenced backyard with a pergola, outdoor fireplace, and soft seating. It offers activities such as kayaking, ping pong, and more. It has a direct access to Lake Howard boat ramp for water activities and is close to Legoland and other major tourist attractions.

About: This Haines City cabin with excellent ratings is located in a peaceful area, yet close to the city center. It's perfect for a relaxing getaway.

The cabin has one bedroom and one bathroom, and can accommodate up to four guests. It features a fully equipped kitchen, air conditioning, a garden, and parking. Pets are also welcome.

About: This B&B is located in the tranquil Winter Haven, offering a serene ambiance for a relaxing retreat. It's just a short distance from the city center, providing easy access to local attractions and amenities.

Highly rated for its cleanliness, location, and overall experience, this B&B offers a comfortable and welcoming stay. It features one bathroom and accommodates up to six guests. Guests can enjoy amenities such as free Wi-Fi, air conditioning, and a garden, making it an ideal choice for families and pet owners seeking a memorable vacation.

About: This apartment for 7 guests is located in Winter Haven, 4 miles from Legoland and near Lake Mariam. It has been given an excellent user rating and is surrounded by theme parks and other major attractions.

The apartment has 3 bedrooms and 2 bathrooms and a spacious layout. It offers a fully equipped kitchen, air conditioning, a garden, parking, and internet.

The unique features of this accommodation include a lakeside location with a private dock, proximity to Legoland and other major attractions, a spacious 2.6-acre property with privacy, a cozy and inviting interior design, and outdoor seating areas with lake views. Kayaking, water skiing, and motor boating are also available nearby.

About: This apartment is located in the heart of Winter Haven, near Inman Park and Lake Conine. It's in a quiet area but within walking distance of the city center.

It has excellent user, location, and cleanliness ratings.

The apartment has 1 bedroom, 1 bathroom, and can accommodate up to 3 guests.

It features a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a terrace/balcony, a garden, parking, and free WiFi. Guests can also enjoy a barbecue on the patio.

About: This apartment is located in Haines City, near Southern Dunes Golf Club and Heart of Florida Regional Medical Center. It is situated within 1 mile of Southern Dunes Golf Club and 6 miles of True Blue Winery.

The apartment has a floor area of 1750 square feet and features 4 bedrooms and 2 bathrooms. It includes a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a terrace or balcony, a garden, a concierge, a restaurant, a fitness center, a tennis court, and parking.

Guests can enjoy free WiFi, an outdoor tennis court, and free self-parking.

About: This apartment is located in Haines City, near LEGOLAND® Florida and within walking distance of Wal-Mart and other amenities. It is also close to other popular tourist destinations, such as Disney World and Universal Studios.

The apartment has received excellent user ratings, and it is easy to see why. It is spacious and well-appointed, with two bedrooms and two bathrooms. It can accommodate up to eight guests, making it ideal for families or groups of friends.

The apartment features a fully equipped kitchen, as well as a living room with a TV and DVD player. It also has a private balcony or patio, where guests can relax and enjoy the views. The complex has a communal pool, a sunbathing area, and an on-site golf club with dining options. There is also 24-hour security and a gated entrance, so guests can feel safe and secure.

About: This waterfront apartment for 10 is located in Winter Haven, Florida, just 5 miles from Legoland and 23 miles from Disney World. It has received excellent user ratings.

The 2300 square feet apartment has 4 bedrooms, 3 bathrooms, a fully equipped kitchen, a dining room, and a laundry room. It also has a heated pool, a hot tub, a terrace, a balcony, a garden, and parking.

Guests can enjoy boating and fishing from the private pier, and they can also relax in the heated pool or hot tub. The apartment is also close to Legoland and other major theme parks.

About: This private lake home is located in Eagle Lake, near Legoland (10 minutes) and Disney attractions (35-40 minutes). It is surrounded by stunning views and offers a cozy interior with a fireplace.

The apartment has very good user ratings.

The apartment has a floor area of 2800 square feet, 4 bedrooms, 4 bathrooms, and a guest capacity of 12.

It features a large pool with a diving board and jacuzzi hot tub, a lakeside screened balcony and patio, a game room with pool table, ping pong, and foosball, a boat dock and fishing, and free high-speed wireless internet.

About: This apartment is located in Winter Haven, a peaceful and picturesque city, known for its beautiful lakes and lush greenery. It is in close proximity to the city center, historical landmarks, and offers easy access to a variety of activities.

The apartment has received excellent ratings for its cleanliness, location, and user experience.

The apartment is suitable for up to 8 guests and features a spacious layout with one bathroom. It has a fully equipped kitchen, air conditioning, and a private garden. Guests can also enjoy access to a shared swimming pool and parking. The apartment's proximity to nearby attractions, such as Legoland Florida and Bok Tower Gardens, makes it an ideal choice for families and travelers seeking a comfortable and convenient stay in Winter Haven.

About: This apartment is located in a quiet neighborhood in Winter Haven. It is close to Legoland and Cypress Gardens, making it an ideal base for exploring the area.

The apartment has received excellent ratings from previous guests, who have praised its cleanliness, location, and amenities.

The apartment has 4 bedrooms, 2 bathrooms, and can accommodate up to 8 guests. It features a fully equipped kitchen, multiple TVs, a private pool, and a playroom.

The private pool is a great place to relax and cool off after a day of exploring Winter Haven. The playroom is perfect for keeping kids entertained, and the fully equipped kitchen makes it easy to prepare meals.

About: This 2-bedroom, 2-bathroom apartment is set on the scenic Lake Lulu in Winter Haven, within walking distance of restaurants. It has received excellent ratings for its location, cleanliness, and user experience.

The apartment features a full kitchen, air conditioning, a swimming pool, a fitness center, and parking. It also includes a washer and dryer, custom blinds, and closet organizers for convenience and privacy. Guests can relax in the gazebo and enjoy the natural surroundings.

About: This apartment is located in a quiet family neighborhood in Winter Haven, minutes from Legoland and Bok Tower Gardens. It has excellent user, location and cleanliness ratings.

The spacious 4-bedroom, 4-bathroom home accommodates up to 11 guests. It features an open concept living space with pool access from multiple rooms, a screened-in pool and private backyard for outdoor relaxation. The dedicated workspace and family-friendly amenities make it a great choice for families and groups.

About: This apartment is located on the waterfront of Eagle Lake, within a 15-minute drive of Legoland, Disney, and Universal Studios. It has excellent user, location, and cleanliness ratings.

The apartment has a floor area of 1690 square feet, 4 bedrooms, 2 bathrooms, and a guest capacity of 8.

It features a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, parking, and stunning lake views. Guests can enjoy boating, fishing, and birdwatching on Eagle Lake.

About: This apartment is located in the Southern Dunes community, minutes from Disney and Universal, close to entertainment and attractions. It has excellent user, location and cleanliness ratings.

With a floor area of 1950 square feet, this apartment can accommodate up to 8 guests in 4 bedrooms and 3 bathrooms.

This apartment features a private pool and spillover spa overlooking the golf course, themed bedrooms for Elsa and Captain America fans, a fully equipped kitchen with amenities for large groups, accessible property with wheelchair-accessible bedrooms and wide hallways, Pack n' Plays, highchair, and tension stair gate available upon request.

About: This apartment is located in Haines City, 3 miles from Southern Dunes Golf Club and 23 miles from Walt Disney World. It offers an excellent user rating.

The apartment has a floor area of 2540 square feet and can accommodate up to 8 guests. It features 4 bedrooms, 5 bathrooms, a fully equipped kitchen, a dining area, a private pool, a covered patio with lake views, air conditioning, internet, parking, and a step-free entry.

The apartment is close to golf courses, parks, and major tourist attractions. It also features a modern and inviting interior design and a bedroom with a bathroom on the first floor.

About: This B&B is located in the heart of Winter Haven, between four beautiful lakes, and near Legoland. The location is perfect for those who want to explore the city and its surroundings.

The B&B has excellent user, location and cleanliness ratings.

This B&B has one private suite with a king-size bed and lake views, as well as a newly renovated bathroom with plenty of storage, a kitchenette and a breakfast bar. The B&B also has a saltwater pool, a bromine Jacuzzi, a screened-in pool area for outdoor dining, and a garden. Laundry is available upon request.

About: This apartment is ideally located in Winter Haven, with an excellent location rating. It is close to many landmarks and the city center, making it an ideal base for exploring the area.

With excellent user and cleanliness ratings, this 3-bedroom, 3-bathroom apartment can accommodate up to 7 guests.

It features a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, and parking. Guests can enjoy nearby activities such as swimming, sunbathing, and exploring the surrounding area.

About: This apartment is located in Winter Haven, near Eagle Ridge Mall, Northgate Shopping Center, Legoland Florida, and is surrounded by parks, lakes, and restaurants. It has an excellent user rating.

The 5-bedroom, 3-bathroom layout can accommodate up to 10 guests. It features a fully equipped kitchen with granite countertops and Nespresso coffee bar, flat-screen TV, air conditioning, jacuzzi, and parking.

About: This apartment is located in a family-friendly neighborhood in Winter Haven, near LEGOLAND® Florida (5 miles) and Water Ski Museum and Hall of Fame (2 miles). It has an excellent user rating.

This 4-bedroom, 3-bathroom apartment can accommodate up to 11 guests.

It features a private backyard with a screened-in pool and covered lanai, a fully equipped kitchen, a dedicated desk space, games and activities for all ages, ample closet space, ceiling fans, and extra bedding in each room.

About: This apartment is located in Winter Haven, near Legoland Florida Resort (10 miles) and Chain O' Lakes Complex (5 miles). It has an excellent user rating.

It is a 3720 square feet apartment with 3 bedrooms and 3 bathrooms, with a guest capacity of 7.

This apartment features a private lakefront with a boat dock and porch swing, a heated pool, a brand-new Bullfrog hot tub, a dedicated home office with a printer, two living rooms, one with an 85-inch Samsung OLED TV and Sonos Arc™ home theater surround sound, three well-appointed bedrooms with Casper sheets and bedding, and a spa-like primary suite with a jetted tub and large two-person shower.

About: This charming B&B is nestled in the heart of Winter Haven, a historic city with many landmarks. It is surrounded by lush gardens and offers a peaceful ambiance.

The B&B has received excellent ratings for its cleanliness, location, and user experience. It features one bathroom and can accommodate up to three guests.

Amenities include air conditioning, internet, a garden, and pet-friendly policies. Nearby activities include exploring the city's historical landmarks and enjoying the beautiful natural surroundings.

About: This apartment is located in the heart of Winter Haven, within walking distance of Legoland Florida and many other attractions. It has received excellent ratings for its location, cleanliness, and user experience.

The apartment has one bedroom, one bathroom, and can accommodate up to three guests. It features a fully equipped kitchen, air conditioning, a garden, and parking. Guests can enjoy the nearby Legoland Florida, as well as other attractions and activities in the area.

About: Located on the lakeside in Winter Haven, this cottage offers serene views and is close to Rotary Park, Baytree Golf Club, and Winter Haven Hospital. It has excellent user ratings.

The cottage has 2 bedrooms, 1 bathroom, and can accommodate up to 3 guests. It features a fully equipped kitchen, smart TV, WiFi, coffee/tea maker, and dishwasher. The terrace/balcony offers stunning lake views.

About: This 1-bedroom apartment is conveniently located in the heart of Winter Haven, within easy walking distance of Inman Park and Lake Conine. It has been rated as excellent by previous guests.

The apartment can accommodate up to 3 guests and has a bedroom, a bathroom, and a cozy living area with a sofa bed. The well-equipped kitchen includes a fridge and microwave, and there is also a private balcony for relaxation. Guests have access to a water park, garden, and barbecue grills.

About: Centrally located in Winter Haven, this family-friendly apartment is within walking distance to downtown entertainment and dining, and a short boat ride away from Legoland. Guests appreciate its excellent location and cleanliness ratings.

This 4-bedroom, 2-bathroom apartment can accommodate up to 9 guests. It features a fully equipped kitchen, air conditioning, a garden, a fitness center, and parking. The backyard offers fun games and puzzles for kids, while the historic charm of the 1908 American classic home adds a unique touch.

About: This centrally located apartment in Winter Haven is just 2 miles from downtown and 4 miles from Legoland and Peppa Pig. It is surrounded by Italian, Mexican, Thai, and Japanese restaurants.

The apartment has earned excellent ratings for its location, cleanliness, and amenities. It has 3 bedrooms, 2 bathrooms, and can accommodate up to 7 guests.

The apartment has a fully equipped kitchen, air conditioning, a garden, and parking. It also has a private dock, a stroller, and toys for children.

About: This fully renovated, family-friendly lake house is centrally located in Eagle Lake, 10 minutes from Legoland, within an hour of Tampa and Disney World. It is surrounded by mature trees and fruit trees, in a quiet non-smoking, pet-free environment.

Rated excellent by previous guests for its location, cleanliness, and amenities, this cottage is the perfect place for a family vacation. It has 2 bedrooms, 1 bathroom, and can accommodate up to 5 guests.

The cottage has a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, internet, a garden, and parking. It also has over an acre of lakefront property with a public boat launch, making it the perfect place to enjoy the outdoors.

About: Centrally located in Winter Haven, this cozy 3-bedroom, 1.5-bath bungalow is within walking distance of downtown entertainment and a half mile from dining and shopping.

With excellent user, location, and cleanliness ratings, this apartment accommodates up to 8 guests and features a fully stocked kitchen, washer & dryer, games, puzzles, DVDs, and a cozy patio.

Unique amenities include a baby chair, crib, and desktop for work or school, as well as a backyard board and bean toss game, charcoal and propane grills.