This Winter Haven lake house boasts a direct Lake Connie waterfront location with a private dock, a short drive from LEGOLAND® Florida Resort and 32 miles from Walt Disney World. The 3-bedroom, 2-bathroom vacation rental sleeps six, features a fully equipped kitchen, private hot tub, screened patio, keyless entry, on-site laundry, and allows well-behaved pets (fee applies).
9.8 159 reviews
Winter Haven
08/03 – 08/12
$72/nighttotal: $648 (9 )
4 A Tiny House W/ Bunk Bed In Quiet Marina Unit 14
1 3
house , Winter Haven
The Cypress Inlet Tiny House is located in Winter Haven, close to Lake Eloise and a short drive from Legoland. The property has received excellent ratings for its cleanliness, location, and overall user experience. This cozy cottage comfortably sleeps up to four guests with a queen-size Murphy bed and two single bunk beds. The Cypress Inlet Tiny House offers amenities like air conditioning, internet access, a garden, and parking, as well as access to boat slips on a canal leading to Lake Eloise.
10 111 reviews
Winter Haven
12/01 – 02/28
$165/nighttotal: $14685 (89 )
Kid-friendly Home W/ Pool & Bbq
1 2
apartment , Winter Haven
This renovated three-bedroom house in Winter Haven, Florida, is conveniently located approximately 20 minutes from LEGOLAND Florida and 50 minutes from Walt Disney World Resort. This family-friendly vacation home boasts a private pool, a fully equipped kitchen with dishwasher, washer/dryer, and accommodates up to seven guests with three bedrooms and two bathrooms.
10 17 reviews
Winter Haven
06/20 – 06/27
$211/nighttotal: $1477 (7 )
2-bedroom, 2-bath Unit Offers A Family-friendly Retreat Just Mins From Legoland.
2 2
apartment , Winter Haven
This Winter Haven apartment rental is conveniently located in a gated community minutes from LEGOLAND Florida and close to several lakes, parks, and wildlife areas including the KICCO Wildlife Management Area. The 1,280-square-foot, two-bedroom, two-bathroom unit sleeps six guests and features a fully equipped kitchen, in-unit washer/dryer, smart TVs, and access to a community pool, fitness center, and playground, plus on-site LEGO sets and games.
9.0 20 reviews
Winter Haven
06/20 – 06/27
$138/nighttotal: $966 (7 )
Lovely Spanish Style Home
1 2
apartment , 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.
9.6 25 reviews
Winter Haven
06/25 – 06/29
$224/nighttotal: $896 (4 )
Family Fun Haven: 3 Bed/2 Bath/6 Mi To Legoland/pet Friendly!
3 5
apartment , Winter Haven
This 3-bedroom, 2-bathroom home is located in Winter Haven, Florida, just a short drive from grocery stores, parks, shopping, and major theme parks like LEGOLAND and Peppa Pig. The apartment is perfect for families and pet owners, offering a fully fenced backyard for outdoor enjoyment. This comfortable home sleeps up to eight guests and features a fully equipped kitchen, modern amenities like a smart TV and washer/dryer, and a safe and secure environment with a keypad entry door and monitored smoke alarm. Enjoy the Florida sunshine in the private backyard, cook meals in the well-stocked kitchen, and relax in the comfortable living spaces.
9.2 10 reviews
Winter Haven
06/25 – 06/29
$295/nighttotal: $1180 (4 )
Spacious Home, In A Quiet Neighborhood Near Legoland®-just A 12-minute Drive
4 5
apartment , Winter Haven
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.
10 2 reviews
Winter Haven
12/01 – 02/28
$194/nighttotal: $17266 (89 )
Modern Legoland Retreat
1 2
apartment , Winter Haven
This family-friendly condo in Winter Haven offers a prime location, just one mile from LEGOLAND and Peppa Pig World, placing you in a district popular with families. This accommodation accommodates up to 8 guests and features a swimming pool, jacuzzi, garden, and a kitchen equipped with a fridge, microwave, and dishwasher, with air conditioning and internet provided.
9.6 54 reviews
Winter Haven
06/25 – 06/29
$267/nighttotal: $1068 (4 )
Live Your Best Florida Life!
1 5
apartment , Winter Haven
LakeHaven, a Winter Haven vacation home, is centrally located, five minutes from Legoland Florida and 45 minutes from Walt Disney World. This three-bedroom, two-bathroom house sleeps eight, boasting a private pool, free Wi-Fi, and easy access to the Chain of Lakes for kayaking and fishing.
8.3 1813 reviews
Winter Haven
08/03 – 08/12
$194/nighttotal: $1746 (9 )
Legoland® Florida Resort
1 3
resort , Winter Haven
LEGOLAND® Florida Resort is located in Winter Haven, Florida, just steps from the LEGOLAND® Florida theme park and a short drive from other attractions like Historic Bok Tower Gardens and Davidson of Dundee candy factory. The resort has received very good ratings for location, cleanliness, and overall experience. The resort offers a variety of accommodations, including hotels and villas. Guests can enjoy amenities such as swimming pools, restaurants, bars, and a concierge service. The resort also features a range of activities for all ages, including nightly entertainment, LEGO Master Model Builder workshops, and free shuttle service to the theme park.
9.6 230 reviews
Winter Haven
06/20 – 06/27
$137/nighttotal: $959 (7 )
Sweet Cottage- 5 Mi To Legoland & 0.5 Mi To Dwntwn
1 2
apartment , Winter Haven
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.
10 9 reviews
Winter Haven
07/10 – 07/11
$266/nightfor 1 night
Downtown Winter Haven Getaway -Near Chain Of Lakes
1 4
apartment , Winter Haven
This 3-bedroom, 2-bathroom house in Downtown Winter Haven offers exclusive access to the entire property, featuring lake views of Lake Howard and is located within walking distance of local dining and entertainment. This pet-friendly rental accommodates up to 7 guests with a full kitchen, air conditioning, garden, and parking, and is conveniently situated just a 15-minute drive from Legoland Florida Resort, with optional lake tours available on the Chain of Lakes.
Our Favorite Family-Friendly Accommodations in Winter Haven
Choosing a lodging built for families in Winter Haven means city attractions are within easy reach, ensuring a much smoother trip for everyone.
Winter Haven
12/01 – 02/28
$149/nighttotal: $13261 (89 )
Lake Cannon Home
1 2
apartment , Winter Haven
This three-bedroom Winter Haven rental is minutes from Legoland Florida and situated across from a scenic lake with a walking path. The 3-bedroom apartment, boasting a fenced backyard, covered patio, private pool, lakefront deck, and ample parking for boats and RVs, comfortably sleeps eight guests and includes a fully equipped kitchen, washer/dryer, and Wi-Fi.
10 33 reviews
Winter Haven
12/01 – 02/28
$150/nighttotal: $13350 (89 )
Legoland Pool House With Suite 4br/2bth
1 2
apartment , Cypress Gardens
This Cypress Gardens guest house, located three miles from LEGOLAND Florida and 30 miles from Disney World, offers convenient access to major attractions. The one-bedroom house sleeps five with two queen beds, a queen air mattress, a full kitchen, private pool, and in-unit washer/dryer; free Wi-Fi, Roku TV, and board games are also provided.
10 1 review
Winter Haven
06/25 – 06/29
$275/nighttotal: $1100 (4 )
260 M² House ∙ 5 Bedrooms ∙ 10 Guests
5 5
house , Winter Haven
This newly renovated, family-friendly house in Winter Haven offers direct lakefront access and is conveniently located 10 miles from Legoland and under 40 miles from Orlando's theme parks. This furnished home accommodates up to 6 guests with 4 bedrooms and 2 bathrooms, featuring a flexible layout with a separate downstairs master suite, high-speed WiFi, free parking, and an outside eating area overlooking the water.
10 136 reviews
Winter Haven
08/03 – 08/12
$200/nighttotal: $1800 (9 )
The Dalt Retreat
1 3
apartment , Cypress Gardens
This 3-bedroom, 2-bathroom apartment is located in Winter Haven, Florida, just a short drive from LEGOLAND and within easy reach of both Orlando and Tampa. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience. The apartment is designed to accommodate up to eight guests and is perfect for families. It offers a fenced backyard, an in-ground pool, a dedicated video game area, a modern interior, a work-friendly desk in the main bedroom, and a variety of amenities including a grill, cooking utensils, pool supplies, and games.
Best Winter Haven accommodation with a kitchen
9.4 64 reviews
Winter Haven
07/10 – 07/11
$187/nightfor 1 night
Quaint Cottage, 6 Miles To Legoland, Pet Friendly!
1 4
apartment , Eagle Lake
This Eagle Lake cottage offers a peaceful family retreat in central Florida, conveniently located near various attractions (specific distances unavailable). The two-bedroom, one-bathroom house sleeps six comfortably, featuring a queen bed, full bed, full-size pull-out couch, fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, Wi-Fi, a fenced yard with firepit, and ample parking.
9.7 6 reviews
Winter Haven
06/20 – 06/27
$157/nighttotal: $1099 (7 )
"Chalet" Lake House/walking Path/fenced Yard/dock
1 2
apartment , Winter Haven
This lakefront ski chalet on Lake Elbert is located just over a mile from downtown Winter Haven, offering convenient access to Legoland (4.8 miles) and the Chain O' Lakes Sports Complex (2.2 miles), with Winter Haven Hospital and Polk State College also 1 mile away. This 2-bedroom, 1-bathroom apartment accommodates up to 6 guests and features direct waterfront access with a private dock, a propane grill, Adirondack chairs for 6, and a cozy den with a sofa sleeper.
10 1 review
Winter Haven
06/20 – 06/27
$149/nighttotal: $1043 (7 )
Sweet Cottage
2 2
house , Winter Haven
This cozy cottage is located in Winter Haven, Florida, just 0.5 miles from downtown and 5 miles from LEGOLAND® Florida. This 710-square-foot house features two bedrooms, one bathroom, and can comfortably accommodate eight guests, offering a fully equipped kitchen, air conditioning, Wi-Fi, a private balcony, and a garden.
10 8 reviews
Winter Haven
06/25 – 06/29
$210/nighttotal: $840 (4 )
Modern Comfort, Pet Friendly, 2 King Beds
2 5
apartment , Winter Haven
Chain of Lakes Cottage, a six-bedroom, three-bathroom house in Winter Haven, Florida, offers convenient access to LEGOLAND Florida, Chain of Lakes Park, and nearby shopping centers. This 1880-square-foot vacation rental accommodates up to five guests and features on-demand towel and linen service, proximity to nature reserves like Circle B Bar Reserve, and easy access to Chain of Lakes Park's events.
Frequently Asked Questions about accommodations in Winter Haven
What are the top attractions and must-see sites in Winter Haven, FL?
Winter Haven is known for its beautiful lakes, so you'll want to check out Legoland Florida, which is a great place for families, and the Chain of Lakes, where you can go boating, fishing, or just relax by the water. Don't miss the historic Polk Museum of Art and the exciting Explorations V Children's Museum.
Which cultural festivals and seasonal events should visitors attend in Winter Haven, FL?
The annual Winter Haven Art Festival in February is a big draw, and you'll want to check out the Winter Haven Christmas Parade in December. The city also hosts a lot of fun events throughout the year, so you'll want to check the local calendar for details.
What are the best accommodations with a pool in Winter Haven?
What are the most convenient modes of transportation within Winter Haven, FL?
Winter Haven is a pretty easy city to get around. Most places are within a short drive, and there's a good public transportation system with buses that run throughout the city. If you want to explore the surrounding areas, you can rent a car or use ride-sharing services like Uber and Lyft.
What are the best accommodations with a jacuzzi in Winter Haven?
What outdoor activities and adventures are popular in and around Winter Haven, FL?
Winter Haven is a great place to enjoy the outdoors. You can go hiking or biking on the many trails around the city, or take a boat out on one of the lakes. If you're looking for something more adventurous, you can go kayaking or paddleboarding, or even try your hand at waterskiing or wakeboarding.
What are the best accommodations for families and kids in Winter Haven?
What types of accommodations are available in Winter Haven, FL?
Winter Haven has a good selection of hotels, motels, and vacation rentals. You can find everything from budget-friendly options to luxurious resorts. There are also several campgrounds in the area if you prefer to stay outdoors.
What are the best pet friendly accommodations in Winter Haven?
The best time to visit Winter Haven is during the spring or fall when the weather is mild and the crowds are smaller. The summers can be hot and humid, but the winter months are generally pleasant.
What are the best accommodations with parking in Winter Haven?
What local dishes and culinary experiences are a must-try in Winter Haven, FL?
Winter Haven is known for its fresh seafood, so you'll want to try some of the local restaurants that specialize in dishes like grouper sandwiches and crab cakes. You should also check out the many barbecue joints in the area.
In which part of Winter Haven, FL should you consider renting accommodation?
It really depends on what you're looking for. If you want to be close to the action, you should consider staying near the downtown area. If you're looking for a more peaceful getaway, you might want to stay near one of the lakes. There are also some great options in the surrounding areas, like Lake Wales and Auburndale.
Destinations nearby
Best Winter Haven lodging with a pool
Among the 577 accommodations in Winter Haven, here are the 4 best ones with a pool
8.0 1 review
Winter Haven
06/20 – 06/27
$406/nighttotal: $2842 (7 )
Ultimate Family Getaway: 4br Home With Pool & Games
4 2
apartment , Winter Haven
This five-bedroom, three-bathroom house in Winter Haven is located within 2 miles of Legoland Florida Resort and Downtown Winter Haven, with Circle B Bar Reserve also nearby. This family-friendly rental sleeps up to 10 guests and features a private swimming pool, fire pit, fenced yard with a BBQ grill, a dedicated kids' room with bunk beds, a semi-private suite with a kitchenette, a fully equipped modern kitchen, a spacious living room with a pool table, and high-speed Wi-Fi.
10 2 reviews
Winter Haven
08/03 – 08/12
$188/nighttotal: $1692 (9 )
South Facing Golf Course Views Southern Dunes Villa
4 3
house , Haines City
This Southern Dunes Villa in Haines City, Florida boasts a tranquil setting with south-facing golf course views, conveniently located 8.8 miles from Swann's Railroad Station and within 20 miles of Legoland Florida and Disney World attractions. This 1,540-square-foot vacation home features four bedrooms, three bathrooms, and accommodates up to 12 guests, offering a fully equipped kitchen, private pool, jacuzzi, and free Wi-Fi.
Winter Haven
06/20 – 06/27
$198/nighttotal: $1386 (7 )
Golf Course Villa, Southern Dunes
3 2
apartment , Haines City
This Haines City vacation home is located a short 15-minute walk from Southern Dunes Golf Club and Country Club and 3.1 miles from Ember Dog Park. This 1,540-square-foot house features three bedrooms, two bathrooms, a private pool, and can comfortably accommodate six guests, with amenities including a fully equipped kitchen, laundry facilities, and a relaxing balcony.
Winter Haven
06/20 – 06/27
$224/nighttotal: $1568 (7 )
Private, Large Pool Villa, Southern Dunes, Golf Course Views
4 2
apartment , Haines City
This Haines City vacation rental, located within the gated Southern Dunes Golf Course and Country Club community, offers easy access to major Orlando attractions like Legoland (15 minutes), Disney World (20 minutes), Universal Studios (under 30 minutes), and SeaWorld (20 minutes), as well as a nearby Walmart Supercenter. The four-bedroom, three-bathroom home sleeps eight guests and features a private pool (optional heating available for a fee), fully equipped kitchen, laundry facilities, high-definition TVs, 200 Mbps WiFi, and enhanced COVID-19 sanitation.
Best Winter Haven accommodation with parking
Winter Haven
06/25 – 06/29
$205/nighttotal: $820 (4 )
4br 3bath Pool Home With Golf Course View, Quiet Cul De Sac In Southern Dunes
4 5
house , Haines City
This 4-bedroom, 3-bathroom pool home in Haines City's Southern Dunes district offers a golf course view and is located 8.8 miles from Swanns Railroad Station (Historical) and 14 miles from Legoland Florida. This 1550 sq ft vacation rental accommodates up to 12 guests with a private swimming pool, air conditioning, a fully equipped kitchen, sun terrace, and an on-site children's playground.
8.8 7 reviews
Winter Haven
06/20 – 06/27
$208/nighttotal: $1456 (7 )
Serene Lakeside Retreat- 3 Bdr Romantic Getaway
3 2
house , Winter Haven
This lakeside home in Winter Haven, Florida, is conveniently located 10 miles from LEGOLAND Florida and 15 miles from both the Elmer and Allied railroad stations. This 1,930-square-foot house features three bedrooms, two bathrooms, and accommodates up to 11 guests, boasting a fully equipped kitchen, free Wi-Fi, private parking, and family-friendly amenities like an indoor play area and outdoor play equipment.
9.2 19 reviews
Winter Haven
12/01 – 02/28
$307/nighttotal: $27323 (89 )
Winter Haven Retreat W/ Private Pool!
3 2
apartment , Cypress Gardens
This Winter Haven vacation home is located less than 3 miles from LEGOLAND® Florida and other family attractions, offering easy access to Cypress Gardens and other nearby entertainment options. This 1940-square-foot house comfortably sleeps six guests, boasting three bedrooms, two bathrooms, a private pool, and a fully equipped kitchen including a refrigerator, microwave, dishwasher, and stovetop, along with in-house games and internet access.
10 1 review
Winter Haven
07/10 – 07/11
$260/nightfor 1 night
2 Bm/french Country Style Dplx
2 4
apartment , Haines City
This Davenport duplex, a centrally located Haines City rental, is 18-27 miles from major theme parks like Legoland, Disney World, SeaWorld, and Universal Studios. This two-bedroom, one-bathroom vacation home sleeps four, features a modern French Country design, a private garden with a BBQ, and offers laundry facilities for an additional weekly fee.