Compare Vacation Rentals & Airbnb in Winter Haven, FL

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Winter Haven, FL vacation rentals
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467 Rentals and Airbnb in Winter Haven, FL

Best family friendly Winter Haven, FL vacation rentals

Among the 467 accommodations in Winter Haven, FL, here are the 4 best family friendly rentals

Tiny Paradise - Winter Haven, FL
9.8 108 reviews
Winter Haven, FL
08/07 – 12/07
$118/nighttotal: $472 (4 )

Tiny Paradise

1 3
cabin , Winter Haven
This pet-friendly Winter Haven lodge is conveniently located near restaurants (8 km) and Legoland Florida (16 km), with Winter Haven's Antrak station a mere 2.4 km walk away.
The self-catering cottage offers keyless entry, a private yard with a dog house, one bedroom, one bathroom, sleeps two guests, and includes amenities such as free coffee, bathrobes, and a water filter.
Serene Lakeside Retreat- 3 Bdr Romantic Getaway - Winter Haven, FL
8.8 7 reviews
Winter Haven, FL
07/07 – 12/07
$331/nighttotal: $1655 (5 )

Serene Lakeside Retreat- 3 Bdr Romantic Getaway

3 4
house , Winter Haven
This lakeside house in Winter Haven, Florida, is situated 16km from Legoland Florida and 24km from various railway stations, offering serene views.
The 179 square metre property sleeps up to 11 guests, boasting three bedrooms, two bathrooms, a fully equipped kitchen, a garden, terrace, free Wi-Fi, private parking, and children's amenities including an indoor play area and outdoor equipment.
5 Br Home With Large Patio, Pool & Outdoor Family Fun - 7 Mins To Legoland! - Winter Haven, FL
9.6 4 reviews
Winter Haven, FL
01/12 – 28/02
$309/nighttotal: $27501 (89 )

5 Br Home With Large Patio, Pool & Outdoor Family Fun - 7 Mins To Legoland!

5 2
apartment , Cypress Gardens
This five-bedroom Cypress Gardens holiday home is situated minutes from water sports and lakes, a 7-8 minute drive from LEGOLAND Florida, and under an hour from Walt Disney World and Universal Studios Florida.
This 161 square metre property boasts a private pool, kids' swing, basketball hoop, and BBQ, sleeping up to 12 guests and offering a king-size master suite with en-suite bathroom, plus further bedrooms with king, queen, and twin beds (convertible to king).
Getaway Clubhouse 5 Mil Legoland & .5 Mil Downtown - Winter Haven, FL
9.8 12 reviews
Winter Haven, FL
08/07 – 12/07
$265/nighttotal: $1060 (4 )

Getaway Clubhouse 5 Mil Legoland & .5 Mil Downtown

3 3
apartment , Winter Haven
This Winter Haven holiday home is conveniently located within 1.6 kilometres of Winter Haven Women's Hospital, Indigo's Family Fun Centre, Indigo's Billiards, Bowling & Games, Rotary Park, and Winter Haven Hospital, offering easy access to local amenities and attractions.
This spacious 150 square metre property boasts three bedrooms, three bathrooms, and can comfortably accommodate eight guests, featuring a fully equipped kitchen, laundry facilities, a garden, and terrace; ideal for families seeking self-catering accommodation near Winter Haven's leisure options.

Best Winter Haven, FL vacation rentals with parking

Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain Of Lakes - Winter Haven, FL
10 10 reviews
Winter Haven, FL
07/07 – 12/07
$302/nighttotal: $1510 (5 )

Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain Of Lakes

3 4
apartment , Winter Haven
This three-bedroom, two-bathroom flat in Winter Haven is a mere 3-minute drive from Sertoma Park and Inman Park, with the Winter Haven Public Library a 12-minute walk away and Indigo's Family Fun Centre just 2 minutes by car.
This pet-friendly accommodation comfortably sleeps eight guests and features on-site laundry facilities, offering convenient access to local attractions such as Theatre Winter Haven, Bartow Airbase History Museum, Bok Tower Gardens, and LEGOLAND® Florida.
Modern Comfort, Pet Friendly, 2 King Beds - Winter Haven, FL
10 8 reviews
Winter Haven, FL
07/07 – 12/07
$293/nighttotal: $1465 (5 )

Modern Comfort, Pet Friendly, 2 King Beds

2 4
apartment , Winter Haven
Chain of Lakes Cottage is situated in Winter Haven, Florida, near LEGOLAND Florida and Chain of Lakes Park, offering easy access to Havendale Plaza and Northgate Shopping Centre, approximately 0.6 km and 1.6 km away respectively.
This six-bedroom, three-bathroom holiday home, boasting 175 square metres of floor space, sleeps five guests and includes on-demand linen and towel service, with nearby wildlife viewing opportunities at Circle B Bar Reserve and Sertoma Park.
Sweet Cottage 5 Mi To Legoland & 0.5 Mi To Dwntwn - Winter Haven, FL
8.8 5 reviews
Winter Haven, FL
08/07 – 12/07
$243/nighttotal: $972 (4 )

Sweet Cottage 5 Mi To Legoland & 0.5 Mi To Dwntwn

2 3
cottage , Winter Haven
This lakeside holiday home in Winter Haven is situated near Winter Haven Women's Hospital and Indigo's Family Fun Centre, within a 2.4km walk, and close to Rotary Park and Indigo's Billiards, Bowling & Games.
The 66 square metre property offers two bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, terrace, garden, parking, and air conditioning.
Charming 3-bedroom House In Fantastic Winter Haven With Wifi, Ac, Community Pool - Winter Haven, FL
10 3 reviews
Winter Haven, FL
07/07 – 12/07
$301/nighttotal: $1505 (5 )

Charming 3-bedroom House In Fantastic Winter Haven With Wifi, Ac, Community Pool

3 4
apartment , Winter Haven
This Winter Haven holiday home is conveniently located 16km from LEGOLAND Florida, 64km from Walt Disney World Resort, and 72km from Busch Gardens Tampa Bay.
Sleeping up to six guests, this three-bedroom, two-bathroom property offers amenities including Wi-Fi, air conditioning, and access to a community pool, dog park, and walking trails, with nearby access to Winter Haven's 50 lakes.

Frequently Asked Questions about vacation rentals in Winter Haven, FL

  • What are the top family-friendly attractions in Winter Haven, FL?

    Legoland Florida is a must-visit for families, with rides, shows, and a water park. The Polk Museum of Art is also a great option, with interactive exhibits and art for all ages. And the Winter Haven Public Library is a great place for kids to spend an afternoon with books and activities.
  • What are the best Airbnb and vacation rentals in Winter Haven, FL?

    Kirkland House #11 - 1br/1 -5ba, The Russell Lake House and 2 Bedroom Apartment are the most popular Airbnb and vacation rentals in Winter Haven, FL among travelers.

  • When is the best time to book a vacation rental in Winter Haven, FL?

    The best time to book a vacation rental is during the spring or fall. The weather is still pleasant, but the crowds are smaller and the prices are lower. You can also try booking a few weeks in advance, especially if you're planning to visit during peak season.
  • What are the most popular Airbnbs in Winter Haven, FL?

    Among the Airbnbs in Winter Haven, FL, Kirkland House #11 - 1br/1 -5ba, Looking For Relaxation?near Legoland And Disney and The Russell Lake House are the most popular ones.

  • What events or festivals should visitors check out in and around Winter Haven, FL?

    The annual Chain of Lakes Festival is a big event with lots of music, food, and activities. The Winter Haven Art Festival is another popular event, showcasing local artists and crafts. And the Legoland Florida theme park hosts various special events throughout the year.
  • What are the best vacation rentals with a pool in Winter Haven, FL?

    Kirkland House #11 - 1br/1 -5ba, The Russell Lake House and 2 Bedroom Apartment are the best vacation rentals with a pool in Winter Haven, FL.

  • What are the best budget-friendly activities in Winter Haven, FL?

    You can take a leisurely walk or bike ride around the Chain of Lakes. There are plenty of parks and green spaces to enjoy, like the Central Park and the Lake Howard Nature Park. You can also visit the Winter Haven Public Library, which is free and has a variety of programs and exhibits.
  • What are the best rentals for families and kids in Winter Haven, FL?

    The best rentals for families and kids in Winter Haven, FL are The Russell Lake House, 2 Bedroom Apartment and Looking For Relaxation?near Legoland And Disney.

  • What are the best restaurants with local dishes in Winter Haven, FL?

    For a taste of local cuisine, try The Grove, they have a great menu of fresh seafood and Southern comfort food. Another great option is The Boathouse Restaurant, they have a beautiful view of the lake and serve up delicious seafood and steaks.
  • What are the best rentals or Airbnbs with a jacuzzi in Winter Haven, FL?

  • What are the best walking or cycling routes in Winter Haven, FL?

    The Chain of Lakes Trail is a popular walking and cycling route, it's about 20 km long and goes around all the lakes in the area. You can also try the Winter Haven Linear Park, it's a paved trail that runs along the CSX railroad tracks.
  • Are there pet-friendly attractions in Winter Haven, FL?

    Yes, many of the parks in Winter Haven are pet-friendly. The Central Park and the Lake Howard Nature Park both have designated areas for dogs. Legoland Florida also has a few pet-friendly areas.
  • What are the benefits of choosing a vacation rental in Winter Haven, FL?

    Vacation rentals offer more space and privacy than a hotel room. They often have kitchens, so you can save money on food by cooking your own meals. And they're often located in more residential areas, so you can get a better feel for the local culture.
  • What are the top sports attractions and facilities in Winter Haven, FL?

    Winter Haven is known for its golf courses, with many public and private courses available. The Chain of Lakes is also a popular spot for water sports, like boating, fishing, and waterskiing. There's also a local YMCA with a range of fitness classes and a swimming pool.

Destinations nearby

Best Winter Haven, FL vacation rentals with a balcony

Peaceful Lakeside Retreat - Winter Haven, FL
9.7 10 reviews
Winter Haven, FL
08/07 – 12/07
$354/nighttotal: $1416 (4 )

Peaceful Lakeside Retreat

3 3
house , Winter Haven
Peaceful Lakeside Retreat, a three-bedroom house in Winter Haven, Florida, enjoys a tranquil lakeside location 9.3km from Legoland Florida and approximately 18km from several railway stations.
This 172 square metre property boasts two living rooms, a fully equipped kitchen, a terrace, garden, spa, parking, and accommodates up to 17 guests, offering excellent value for families or large groups.
Beautiful 3 Bedroom Pool Villa In Southern Dunes - Winter Haven, FL
9.4 3 reviews
Winter Haven, FL
08/07 – 12/07
$324/nighttotal: $1296 (4 )

Beautiful 3 Bedroom Pool Villa In Southern Dunes

3 3
apartment , Haines City
This Haines City holiday home is situated within a 15-minute walk of Southern Dunes Golf Club and Country Club, and within 9.6 kilometres of both the regional medical centre and Ember Dog Park.
This three-bedroom, three-bathroom property boasts 139 square metres of living space, comfortably accommodating six guests and featuring a private pool, fully equipped kitchen, and in-house laundry facilities.
Work, Play Or Recharge:3br Pool Home Near Legoland - Winter Haven, FL
10 2 reviews
Winter Haven, FL
27/06 – 04/07
$316/nighttotal: $2212 (7 )

Work, Play Or Recharge:3br Pool Home Near Legoland

3 2
apartment , Winter Haven
This family-friendly apartment in Winter Haven is situated just a 2-minute drive from Indigo's Family Fun Centre and a 3-minute drive from Chain of Lakes Park.
Offering 195 square meters of living space, this residence accommodates up to five guests with three bedrooms and three bathrooms, featuring a private swimming pool, enclosed porch, fully equipped kitchen, and on-site barbecue grill.
Peaceful Lakeside Retreat - Winter Haven, FL
9.2 11 reviews
Winter Haven, FL
07/07 – 12/07
$382/nighttotal: $1910 (5 )

Peaceful Lakeside Retreat

3 4
apartment , Winter Haven
This lakeside property in Winter Haven is situated 1.9km from Sertoma Park and within 4.8km of Indigo's Billiards, Bowling & Games, and Indigo's Family Fun Center.
This 563 square metre house offers four bedrooms, two bathrooms, sleeps seven guests, and boasts a fully equipped kitchen, garden, free Wi-Fi, and parking; water activities are available at the lake.

Best Winter Haven, FL vacation rentals with air conditioning

2-bedroom, 2-bath Unit Offers A Family-friendly Retreat Just Mins From Legoland. - Winter Haven, FL
10 26 reviews
Winter Haven, FL
01/12 – 28/02
$294/nighttotal: $26166 (89 )

2-bedroom, 2-bath Unit Offers A Family-friendly Retreat Just Mins From Legoland.

2 2
apartment , Winter Haven
This two-bedroom, two-bathroom apartment in a gated Winter Haven community is located minutes (approximately 1-2 km) from LEGOLAND Florida and close to other attractions such as Theatre Winter Haven and Chain of Lakes Park.
The 119 square metre property offers a spacious layout sleeping up to six guests, boasting a fully equipped kitchen, in-unit laundry, smart TVs, a private garden, and access to resort-style amenities including a heated pool, fitness centre, and tennis court.
Resort Home In Haines City: Screened Lanai, Pool! - Winter Haven, FL
9.8 13 reviews
Winter Haven, FL
02/07 – 06/07
$639/nighttotal: $2556 (4 )

Resort Home In Haines City: Screened Lanai, Pool!

4 9
resort , Haines City
This Haines City holiday home, 'Resort Home In Haines City: Screened Lanai, Pool!', is situated within 5km of Ember Dog Park and Southern Dunes Golf Club, and 10km from the Lewis W. Mathews Memorial Sports Complex.
The 236 square metre property boasts five bedrooms, five bathrooms, sleeps ten guests, and includes a private pool, hot tub, games room, and is close to several golf courses.
Costa Lego Pool Home - 5br Winter Haven Private Resort - Winter Haven, FL
Winter Haven, FL
02/07 – 06/07
$1119/nighttotal: $4476 (4 )

Costa Lego Pool Home - 5br Winter Haven Private Resort

5 9
house , Cypress Gardens
This private resort in Winter Haven offers a secluded experience, located approximately 4.8 kilometres from Swanns Railroad Station and 4.8 kilometres from Legoland Florida.
This one-bedroom accommodation for up to 23 guests features air conditioning, complimentary WiFi, a fully equipped kitchen, a private swimming pool, and terrace access, with parking also provided.
Historic, Sleeps 10+, 5 Bedroom, Huge Yard, Lake, Fishing, Parks, Events\n - Winter Haven, FL
9.8 32 reviews
Winter Haven, FL
02/07 – 06/07
$501/nighttotal: $2004 (4 )

Historic, Sleeps 10+, 5 Bedroom, Huge Yard, Lake, Fishing, Parks, Events\n

5 9
apartment , Winter Haven
This five-bedroom, three-bathroom family home in Winter Haven, Florida, is located within 1.6km of Winter Haven Hospital and Rotary Park, and under 5km from Indigo's Family Fun Center.
Offering 314 square metres of living space, this property sleeps up to 10 guests and boasts a fully equipped kitchen, garden, terrace, free Wi-Fi, and a fireplace; nearby attractions include Inman Park.
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