Search accommodations in Winter Haven

577 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Winter Haven accommodations
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

577 Lodgings in Winter Haven

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.

Lake Cannon Home - Winter Haven
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.
Legoland Pool House With Suite 4br/2bth - Winter Haven
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.
260 M² House ∙ 5 Bedrooms ∙ 10 Guests - Winter Haven
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.
The Dalt Retreat - Winter Haven
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

Quaint Cottage, 6 Miles To Legoland, Pet Friendly! - Winter Haven
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.
"Chalet" Lake House/walking Path/fenced Yard/dock - Winter Haven
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.
Sweet Cottage - Winter Haven
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.
Modern Comfort, Pet Friendly, 2 King Beds - Winter Haven
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.
  • What are the best accommodations in Winter Haven?

    Among the accommodations in Winter Haven, Best Western Plus Winter Haven Inn & Suites, Holiday Inn Winter Haven By Ihg and Courtyard By Marriott Winter Haven are the most popular ones.

  • 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?

  • When is the best time to visit Winter Haven, FL?

    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

Ultimate Family Getaway: 4br Home With Pool & Games - Winter Haven
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.
South Facing Golf Course Views Southern Dunes Villa - Winter Haven
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.
Golf Course Villa, Southern Dunes - Winter Haven
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.
Private, Large Pool Villa, Southern Dunes, Golf Course Views - Winter Haven
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

4br 3bath Pool Home With Golf Course View, Quiet Cul De Sac In Southern Dunes - Winter Haven
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.
Serene Lakeside Retreat- 3 Bdr Romantic Getaway - Winter Haven
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.
Winter Haven Retreat W/ Private Pool! - Winter Haven
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.
2 Bm/french Country Style Dplx - Winter Haven
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.
©2026 cozycozy.com