
Island In The Sky, Winter Haven
10/23 – 10/26
$161/nighttotal: $483 (3 )
Luxury Staycomfy At Winterheaven
2 2apartment , Winter Haven
This Winter Haven vacation home is conveniently located near Inman Park and Lake Conine, a 15-minute walk away, and less than 2 miles from Winter Haven Hospital and Rotary Park.
This two-bedroom, one-bathroom house sleeps six guests and offers free Wi-Fi, a Smart TV, a fully equipped kitchen with appliances including a dishwasher, in-unit laundry, and on-site parking.
This two-bedroom, one-bathroom house sleeps six guests and offers free Wi-Fi, a Smart TV, a fully equipped kitchen with appliances including a dishwasher, in-unit laundry, and on-site parking.

Island In The Sky, Winter Haven
10/23 – 10/26
$163/nighttotal: $489 (3 )
3 Bedroom Cozy Home With The Perfect Patio
2 2apartment , Winter Haven
This Winter Haven house rental, perfect for families, offers a two-bedroom, two-bathroom home with a private patio and garden in a residential area—exact location within Winter Haven unspecified but likely near parks or green spaces.
The 6-guest home includes a fully equipped kitchen with fridge, microwave, dishwasher, and in-unit laundry; free WiFi and air conditioning are also provided.
The 6-guest home includes a fully equipped kitchen with fridge, microwave, dishwasher, and in-unit laundry; free WiFi and air conditioning are also provided.

Island In The Sky, Winter Haven
08/19 – 08/26
$180/nighttotal: $1260 (7 )
Best Sunsets In Winter Haven. Lakefront Home 5 Minutes From Downtown!
2 4apartment , Winter Haven
This Winter Haven vacation home is conveniently located 1.2 miles from Rotary Park, within 3 miles of Winter Haven Hospital and Winter Haven Women's Hospital, and also near Lake Conine and Indigo's Family Fun Center.
This two-bedroom, two-bathroom house sleeps four and features a fully equipped kitchen, patio, Smart TV, and parking; enjoy nearby outdoor recreation and family fun.
This two-bedroom, two-bathroom house sleeps four and features a fully equipped kitchen, patio, Smart TV, and parking; enjoy nearby outdoor recreation and family fun.

Island In The Sky, Winter Haven
08/19 – 08/26
$474/nighttotal: $3318 (7 )
Lakeside Adventure Retreat W/ Heated Pool, Fishing Dock, Game Room & Optional 1 Hr Boat Cruise*
4 4apartment , Winter Haven
This luxurious lakefront houseboat on Lake Otis in Winter Haven, Florida, is 4.5 miles from LEGOLAND Florida and 28 miles from Walt Disney World.
The 4,740-square-foot property sleeps 10 guests in four bedrooms and five bathrooms and boasts a heated saltwater pool, tennis court, and complimentary one-hour pontoon boat excursion (additional time fees apply).
The 4,740-square-foot property sleeps 10 guests in four bedrooms and five bathrooms and boasts a heated saltwater pool, tennis court, and complimentary one-hour pontoon boat excursion (additional time fees apply).

Island In The Sky, Winter Haven
06/26 – 06/30
$171/nighttotal: $684 (4 )
Downtown Winter Haven Retreat | Arcade + Fast Wifi
3 3apartment , Winter Haven
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 pet-friendly, 3-bedroom unit accommodates up to 5 guests and features a full kitchen, air conditioning, WiFi, and an arcade machine for entertainment.

Island In The Sky, Winter Haven
06/26 – 06/30
$227/nighttotal: $908 (4 )
Serene, Family Lakefront Home With Jacuzzi
1 3apartment , Winter Haven
This two-bedroom, two-bathroom lakefront apartment in Winter Haven offers direct access to the Chain of Lakes, perfect for boating and watersports.
The 7-guest unit features a fully equipped kitchen, washer/dryer, free parking, and kayaks, boats, and jet skis are readily available for guest use.
The 7-guest unit features a fully equipped kitchen, washer/dryer, free parking, and kayaks, boats, and jet skis are readily available for guest use.

Island In The Sky, Winter Haven
08/19 – 08/26
$240/nighttotal: $1680 (7 )
Hook, Line & Leisure: Lakefront Gem W/ Porch!
3 4house , Winter Haven
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.
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.

Island In The Sky, Winter Haven
06/26 – 06/30
$231/nighttotal: $924 (4 )
Luxury By Legoland 104
1 3apartment , Winter Haven
This two-bedroom, two-bathroom ground-floor apartment is located in a brand-new 2024 luxury complex less than one mile from LEGOLAND® Florida Resort in Winter Haven, near the Chain of Lakes.
This family-friendly rental boasts a LEGO-themed kids' bedroom, a fully equipped kitchen with dishwasher, in-unit laundry, smart TVs, and access to a heated pool, fitness center, and other resort amenities; it comfortably sleeps six guests.
This family-friendly rental boasts a LEGO-themed kids' bedroom, a fully equipped kitchen with dishwasher, in-unit laundry, smart TVs, and access to a heated pool, fitness center, and other resort amenities; it comfortably sleeps six guests.

Island In The Sky, Winter Haven
10/23 – 10/26
$122/nighttotal: $366 (3 )
Chain Of Lakes Efficiency # 4
1 2house , Winter Haven
This cozy Winter Haven efficiency unit, located in a cottage near Legoland Florida and Cypress Gardens, offers a convenient base for exploring central Florida attractions.
The 1-bedroom, 1-bathroom unit sleeps up to 2 guests and includes a queen-size bed, loveseat sleeper, kitchenette with a two-burner cooktop and bar sink, shared laundry, and access to a shared yard; pets are welcome.
The 1-bedroom, 1-bathroom unit sleeps up to 2 guests and includes a queen-size bed, loveseat sleeper, kitchenette with a two-burner cooktop and bar sink, shared laundry, and access to a shared yard; pets are welcome.

Island In The Sky, Winter Haven
06/26 – 06/30
$170/nighttotal: $680 (4 )
Lovely Spanish Style Home
1 3apartment , Winter Haven
This 2-bedroom, 2-bathroom rental home in Winter Haven offers a historic 100-year-old Spanish-style experience just 5280 feet from Lake Howard and near Peace River Park, with downtown Winter Haven's attractions a 5-minute drive away.
This accommodation is equipped with air conditioning, internet, and parking, and can host up to 4 guests, serving as an ideal base for exploring the Central Florida chain of lakes.
This accommodation is equipped with air conditioning, internet, and parking, and can host up to 4 guests, serving as an ideal base for exploring the Central Florida chain of lakes.

Island In The Sky, Winter Haven
08/19 – 08/26
$184/nighttotal: $1288 (7 )
Bright Cypress Gardens Home Near Legoland!
3 4apartment , Cypress Gardens
This 3-bedroom vacation home is located in Winter Haven, Florida, just a short drive from Cypress Gardens and close to attractions like LEGOLAND® Florida and Baytree Golf Club. Guests consistently rate this rental as "excellent" for its comfortable accommodations and convenient location.
The 1,470 square foot home comfortably sleeps up to 6 guests and includes amenities like a fully equipped kitchen, washer and dryer, internet access, and a foosball table for entertainment.
The 1,470 square foot home comfortably sleeps up to 6 guests and includes amenities like a fully equipped kitchen, washer and dryer, internet access, and a foosball table for entertainment.

Island In The Sky, Winter Haven
08/19 – 08/26
$264/nighttotal: $1848 (7 )
Lakefront 3 Story 5/3 Bungalo With Huge Yard, Great Views, A Firepit And A Dock.
5 4apartment , Winter Haven
This Winter Haven lakefront house offers direct access to water activities like kayaking and water skiing, and is conveniently located near LEGOLAND Florida and Indigo's Family Fun Center.
The 4-bedroom, 2-bathroom home sleeps 6, features a fully renovated interior with multiple sitting areas, dedicated workspaces, and several dining areas, including an outdoor space overlooking the lake, plus a spa, Wi-Fi, and parking.
The 4-bedroom, 2-bathroom home sleeps 6, features a fully renovated interior with multiple sitting areas, dedicated workspaces, and several dining areas, including an outdoor space overlooking the lake, plus a spa, Wi-Fi, and parking.













