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Winter Haven vacation rentals
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Best Vacation rentals and Airbnb offers in Winter Haven

Top Vacation Rentals for Families in Winter Haven

These family-friendly vacation rentals in Winter Haven offer spacious layouts and easy access to top city attractions.

Modern Comfort, Pet Friendly, 2 King Beds - Winter Haven
10 8 reviews
Winter Haven
12/01 – 02/28
$339/nighttotal: $30171 (89 )

Modern Comfort, Pet Friendly, 2 King Beds

2 2
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.
Getaway Clubhouse 5 Mil Legoland & .5 Mil Downtown - Winter Haven
9.9 51 reviews
Winter Haven
07/08 – 07/12
$175/nighttotal: $700 (4 )

Getaway Clubhouse 5 Mil Legoland & .5 Mil Downtown

3 3
apartment , Winter Haven
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.
Family Fun: Pool, Arcade Games - Winter Haven
9.7 42 reviews
Winter Haven
07/08 – 07/12
$196/nighttotal: $784 (4 )

Family Fun: Pool, Arcade Games

1 3
apartment , Cypress Gardens
This Cypress Gardens family home, located two miles from LEGOLAND Florida, offers easy access to area attractions.
The two-bedroom, two-bathroom vacation rental sleeps six, features a private pool with games, a dedicated bunk room, classic arcade games, and additional family-friendly games like jumbo checkers and cornhole.
Legoland® Florida Resort - Winter Haven
8.3 1815 reviews
Winter Haven
06/27 – 07/04
$315/nighttotal: $2205 (7 )

Legoland® Florida Resort

1 2
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.

Best Winter Haven vacation rentals with parking

Updated Pool Villa, Southern Dunes - Winter Haven
10 1 review
Winter Haven
07/16 – 07/20
$294/nighttotal: $1176 (4 )

Updated Pool Villa, Southern Dunes

3 2
apartment , Haines City
This apartment is located in Haines City within the Southern Dunes Golf Course & Country Club, offering proximity to Legoland (20 miles), Walt Disney World (30 miles), and SeaWorld and Universal Theme Parks (40 miles), with local shops and a Wal-Mart Supercenter within walking distance. This 1540 sq ft villa features 3 bedrooms, 2 bathrooms, and accommodates up to 6 guests, boasting a private screened-in pool lanai, high-speed WiFi, Smart TVs, and access to community amenities such as pools and tennis courts, all within a gated community with 24-hour security.
Cheerful 4 Bed, 3 Bath Home With Screened Pool - Winter Haven
9.8 28 reviews
Winter Haven
12/01 – 02/28
$388/nighttotal: $34532 (89 )

Cheerful 4 Bed, 3 Bath Home With Screened Pool

4 2
apartment , Winter Haven
This 4-bedroom apartment in Winter Haven is a short drive from Theatre Winter Haven and the Water Ski Museum and Hall of Fame, making it a great base for exploring the city's attractions. Guests consistently rate this rental as excellent, making it a popular choice for families and groups. The spacious home has multiple living areas and sleeps up to 11 guests comfortably. Amenities include a private pool, a screened-in lanai, a well-equipped kitchen, a dedicated workspace, and a game room, ensuring everyone has plenty to do during their stay.
*Centrallocated*privatekingsuitew/bath, Washer&dryer(eagle) - Winter Haven
8.4 9 reviews
Winter Haven
07/08 – 07/12
$126/nighttotal: $504 (4 )

*Centrallocated*privatekingsuitew/bath, Washer&dryer(eagle)

1 3
apartment , Winter Haven
This Winter Haven apartment is conveniently located within a 3-mile radius of attractions like Rotary Park, Winter Haven Hospital, and Inman Park, making it a great base for exploring the city. It's also highly rated by previous guests, earning a "very good" user rating.
The apartment can accommodate up to 3 guests and features a comfortable layout with one bedroom and one bathroom. Amenities include a fully equipped kitchen, air conditioning, free Wi-Fi, and parking on-site, ensuring a relaxing and convenient stay.
Game Room + Fenced Yard: Home Near Disney World! - Winter Haven
9.4 29 reviews
Winter Haven
06/27 – 07/04
$184/nighttotal: $1288 (7 )

Game Room + Fenced Yard: Home Near Disney World!

4 2
house , Haines City
This Haines City vacation home is conveniently located just 17 miles from Carters Railroad Station, 19 miles from Elmer Railroad Station, and 9 miles from Swanns Railroad Station (Historical), providing easy access to explore the surrounding area. This property consistently receives excellent ratings for cleanliness, location, and overall user experience.
This spacious 4-bedroom rental, accommodating up to 10 guests, boasts a fully equipped kitchen, a private yard, a game room, and modern amenities like free Wi-Fi and air conditioning. Enjoy a peaceful retreat with comfortable accommodations, perfect for families or groups seeking a relaxing vacation.

Frequently Asked Questions about vacation rentals in Winter Haven

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

    Legoland Florida is a no-brainer, especially for younger kids. For something different, head to the Polk Museum of Art, they have interactive exhibits and events for families. And if you're looking for some outdoor fun, the Chain of Lakes offers boat rentals and fishing spots.
  • What are the best Airbnb and vacation rentals in Winter Haven?

    Walton House #7 - 2br / 2ba, The Russell Lake House and 2 Bedroom Apartment are the most popular Airbnb and vacation rentals in Winter Haven among travelers.

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

    The best time to book a vacation rental in Winter Haven is during the shoulder seasons, spring and fall. You'll get better deals and avoid the crowds. The weather is still pleasant, too.
  • What are the most popular Airbnbs in Winter Haven?

    Among the Airbnbs in Winter Haven, Walton House #7 - 2br / 2ba, 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 Winter Haven Art Festival is a big event, it's held in February and features art, music, and food. If you're visiting in the fall, the Florida Strawberry Festival in Plant City is worth the short drive, it's a fun event with rides, concerts, and of course, strawberries!
  • What are the best vacation rentals with a pool in Winter Haven?

    Walton House #7 - 2br / 2ba, The Russell Lake House and 2 Bedroom Apartment are the best vacation rentals with a pool in Winter Haven.

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

    For a taste of Florida, try the fried green tomatoes at The Terrace Restaurant. If you're looking for something more casual, The Deck on the Lake has great views and a good selection of seafood. And for a sweet treat, you can't go wrong with a slice of pie at the Winter Haven Pie Company.
  • What are the best rentals for families and kids in Winter Haven?

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

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

    The Chain of Lakes Trail is a great option for both walking and cycling, it's a paved trail that goes around several of the lakes. For a shorter walk, check out the Winter Haven Public Library gardens, they're beautiful and peaceful.
  • What are the best rentals or Airbnbs with a jacuzzi in Winter Haven?

  • Are there pet-friendly attractions in Winter Haven, FL?

    Yes, there are! Legoland Florida is pet-friendly, they have a designated area for dogs. The Chain of Lakes is also a great place to take your furry friend for a walk or a swim.
  • What are the benefits of choosing a vacation rental in Winter Haven, FL?

    Vacation rentals offer more space and privacy than hotels, and you can often find rentals with amenities like kitchens and laundry facilities. They're also a good option for families and groups, as you can often find rentals with multiple bedrooms and bathrooms.

Destinations nearby

Best Vacation Rentals with Balconies in Winter Haven

Start your morning right with a vacation rental in Winter Haven featuring a private balcony and stunning views.

Private/spacious 1br Central Near Legoland 2 Miles - Winter Haven
9.0 13 reviews
Winter Haven
06/27 – 07/04
$121/nighttotal: $847 (7 )

Private/spacious 1br Central Near Legoland 2 Miles

1 2
apartment , Cypress Gardens
This vacation home is centrally located in Winter Haven, 2 miles from downtown, the hospital, LEGOLAND, and Peppa Pig. It has an excellent user rating.
The apartment has 1 bedroom, 1 bathroom, and a guest capacity of 5. It features a fully equipped kitchen, a comfortable living room, a spacious master bedroom, a private screened-in porch, a large fenced-in yard, and access to a community pool. Activities or services available at the accommodation include a private screened-in porch, a large fenced-in yard, and access to a community pool.
Winter Haven Apt: 1 Mi To Polk State College! - Winter Haven
10 2 reviews
Winter Haven
07/16 – 07/20
$113/nighttotal: $452 (4 )

Winter Haven Apt: 1 Mi To Polk State College!

1 2
apartment , Winter Haven
This Winter Haven apartment rental is conveniently located within one mile of Rotary Park and Winter Haven Hospital, and within three miles of Winter Haven Women's Hospital and Indigo's Family Fun Center.
The pet-friendly unit features a private balcony, a fully equipped kitchen, free Wi-Fi, and free self-parking, along with in-unit amenities such as a ceiling fan, shower, and iron/ironing board.
Costa Lego Pool Home - 5br Winter Haven Private Resort - Winter Haven
Winter Haven
07/02 – 07/06
$800/nighttotal: $3200 (4 )

Costa Lego Pool Home - 5br Winter Haven Private Resort

5 9
house , Cypress Gardens
This Winter Haven residence offers a private resort feel, situated 3 miles from Legoland Florida and providing direct access to a terrace.
This 1-bedroom, 3-bathroom home accommodates 23 guests and features a private swimming pool, fully equipped kitchen, air conditioning, free WiFi, and free private parking.
South Facing Golf Course Villa, Updates Throughout! - Winter Haven
Winter Haven
07/07 – 07/12
$270/nighttotal: $1350 (5 )

South Facing Golf Course Villa, Updates Throughout!

4 4
apartment , Haines City
This Haines City vacation home is located less than a mile from Southern Dunes Golf Club and Country Club, and within six miles of regional medical facilities and a dog park.
This 1,540-square-foot house features four bedrooms, three bathrooms, a private pool, and can comfortably accommodate eight guests, offering in-house laundry and a fully equipped kitchen.

Best Winter Haven vacation rentals with air conditioning

The Lake Alfred Citrus Wood Guest Cabin\n\n - Winter Haven
9.8 50 reviews
Winter Haven
07/16 – 07/20
$125/nighttotal: $500 (4 )

The Lake Alfred Citrus Wood Guest Cabin\n\n

1 2
cabin , Lake Alfred
This Lake Alfred cottage is located 1 mile from Lake Conine and within 3 miles of Lions Park and Inman Park, offering easy access to outdoor recreation and local amenities.
The one-bedroom, one-bathroom rental sleeps three guests and includes Wi-Fi, air conditioning, on-site laundry, and is pet-friendly, perfect for a relaxing getaway near Auburndale City Park and Winter Haven Hospital.
Charming Boutique Apt/quiet Stay/ Near Lakes &Dw - Winter Haven
10 20 reviews
Winter Haven
06/27 – 07/04
$172/nighttotal: $1204 (7 )

Charming Boutique Apt/quiet Stay/ Near Lakes &Dw

1 2
house , Winter Haven
Cozy Vintage Apartment D in Winter Haven offers a peaceful location near a lake, minutes from restaurants, shops, hospitals, and universities.
This one-bedroom, one-bathroom unit features a full kitchen, living room with a sofa bed, accommodating up to three guests and includes access to a shared backyard, parking, and a BBQ grill.
Carefree Cove On Lake Connie - With Hot Tub! - Winter Haven
9.7 82 reviews
Winter Haven
07/07 – 07/12
$198/nighttotal: $990 (5 )

Carefree Cove On Lake Connie - With Hot Tub!

1 4
apartment , Winter Haven
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).
Cozy 2-bedroom House In A Beautiful Winter Haven Area Near Legoland And Boktower - Winter Haven
10 3 reviews
Winter Haven
07/03 – 07/07
$204/nighttotal: $816 (4 )

Cozy 2-bedroom House In A Beautiful Winter Haven Area Near Legoland And Boktower

2 3
apartment , Winter Haven
This 2-bedroom, 1-bathroom vacation rental is located in Winter Haven, just a 4-minute drive from LEGOLAND® Florida and Chain Of Wakes.
This pet-friendly apartment offers Wi-Fi, air conditioning, a garden, spa, and parking, with nearby opportunities for motorboating, cycling, and fishing.
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