Compare temporary rentals in Winter Haven from 100+ providers!

This canal-view casita in Winter Haven offers direct access to the Chain of Lakes and is located approximately 5 miles from LEGOLAND Florida Resort and 2 miles from downtown Winter Haven.
This family-friendly vacation home accommodates up to 6 guests with 3 bedrooms, 1 bathroom, a full kitchen, air conditioning, and a screened lanai, providing ample space for relaxation and entertainment.

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 Winter Haven apartment rental is conveniently located within walking distance of downtown Winter Haven, Lake Howard, and numerous restaurants, and a short drive from Legoland Florida (12 minutes) and major theme parks (45 minutes).
This three-bedroom, two-bathroom unit sleeps six guests comfortably, offering two queen beds and two twin beds, plus amenities including a microwave, dishwasher, washer/dryer, Wi-Fi, and parking; nearby attractions include the Winter Haven Hospital (5 minutes away), AdventHealth Fieldhouse (6 minutes away), and outdoor recreation at The Circle B Bar Reserve and Rotary Park.

This downtown Winter Haven condo offers prime access to shops and dining, with local attractions just minutes away.
This pet-friendly, 3-bedroom unit accommodates up to 5 guests and features a full kitchen, air conditioning, WiFi, and an arcade machine for entertainment.

This Eagle Lake apartment rental is conveniently located near LEGOLAND® Florida and offers easy access to shopping at Northgate Shopping Center and Eagle Ridge Mall, plus recreational options at Chain of Lakes Park and Winter Haven City Tennis Center.
The 1000-square-foot unit features two bedrooms, two bathrooms, a king bed and a bunk bed, accommodating up to six guests, a private pool with lake views, and amenities including WiFi, air conditioning, and a microwave.

This family-friendly vacation rental in Winter Haven is conveniently located near Legoland Florida, a 15-minute drive away, and the Polk Museum of Art, a 10-minute drive away. The 3-bedroom, 2-bathroom home sleeps up to 8 guests and includes a fully equipped kitchen, a relaxing garden, and entertainment options like board games and foosball.

This 2-bedroom, 2-bathroom condo offers prime waterfront living on Lake Winterset within the exclusive Winterset gated community, providing direct access to the renowned Chain of Lakes and situated within a 90-minute drive of both Florida coasts.
This family-friendly residence accommodates up to 6 guests with amenities including a community swimming pool, Jacuzzi, tennis courts, a kayak ramp, and a karaoke machine, all within a secure, tranquil setting ideal for outdoor activities.

This Cypress Gardens apartment is located in Winter Haven, Florida, just 5 minutes from Legoland and the new Peppa Pig theme park, and across the street from Lake Ned Park. The apartment has excellent user, location, and cleanliness ratings.
The apartment is perfect for families with 3 bedrooms and 2 bathrooms, accommodating up to 10 guests. Amenities include a private pool, a Lego-themed kids room, a crib, a full-sized bunk bed with a trundle, a bonus room/office, and a fenced-in backyard.

This Cypress Gardens hotel is located near the main attractions and landmarks, offering a convenient base for exploring the area. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The hotel has four unique rooms, each with private access and a maximum of two people per room, accommodating up to eight guests. Amenities include a rooftop deck, a mermaid pool with an observation lounge, a hot tub, a washing machine, and a shop, providing a relaxing and convenient experience.

This 4-bedroom, 4-bathroom home is located near Eagle Lake, within easy reach of both Legoland and Disneyworld. It boasts excellent user, location, and cleanliness ratings, making it a great choice for travelers. The spacious rental provides ample room for up to 12 guests, ensuring a comfortable stay for families or groups. Amenities include a private pool with a diving board, a hot tub, a garden, and access to the lake for boating and jet skiing, making it a perfect option for a relaxing vacation.

This Winter Haven lakefront rental boasts direct access to Lake Mirror and a private dock, ideal for water sports enthusiasts.
The 3-bedroom, 2-bathroom apartment features a 22x22 foot covered patio, a heated swim spa (14x8 feet), paddle boards, kayaks, outdoor TVs, and a fully equipped kitchen; it comfortably sleeps 9 guests.

This spacious Winter Haven vacation home is located within two miles of Inman Park, Lake Conine, and Winter Haven Hospital, and three miles from Indigo's Family Fun Center and Indigo's Billiards.
Boasting 3,300 square feet, this six-bedroom, four-bathroom residence comfortably sleeps 22 guests and features a fully equipped kitchen, a private game room, a hot tub, and a tennis court.

This 1-bedroom, 1-bathroom condo in Winter Haven is located just a short distance from LEGOLAND® Florida, offering convenient access to the Chain of Lakes, local shopping, and dining.
This pet-friendly residence provides parking, a fully equipped kitchen with a microwave and dishwasher, air conditioning, and in-unit laundry, accommodating up to 4 guests with self check-in.