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Best Vacation rentals and Airbnb offers in Winter Haven
10 2 reviews
Winter Haven
06/25 – 06/29
$174/nighttotal: $696 (4 )
Cozy Bungalow
3 5
house , Winter Haven
This Winter Haven bungalow is conveniently located half a mile from downtown and five miles from LEGOLAND Florida. The 1420-square-foot home features three bedrooms, one bathroom, a fully equipped kitchen with a dishwasher and microwave, and accommodates up to 15 guests, with a terrace, garden, and free Wi-Fi.
9.8 7 reviews
Winter Haven
12/01 – 02/28
$191/nighttotal: $16999 (89 )
- Hidden Gem - Spacious, Minimal And Clean! Legoland + Disney
4 2
apartment , Winter Haven
This Winter Haven vacation home is conveniently located within 6 miles of Sertoma Park, Winter Haven Hospital, and Inman Park, with easy access to Lake Conine and Auburndale City Park. This four-bedroom, two-bathroom house sleeps nine guests and includes in-house laundry facilities, essential bathroom amenities, and is close to parks offering walking trails and picnic areas.
9.8 38 reviews
Winter Haven
07/10 – 07/11
$359/nightfor 1 night
Florida Dream Vacation House
1 4
apartment , Cypress Gardens
This Winter Haven home, near Legoland and Disney, offers easy access to Cypress Gardens and other Central Florida attractions. The 3-bedroom, 2-bathroom house sleeps 8, features a private pool, game room with pool table, foosball, and piano, in-house washer/dryer, and TVs with Roku and Netflix access in each bedroom.
9.6 8 reviews
Winter Haven
06/25 – 06/29
$227/nighttotal: $908 (4 )
Newly Remodeled Lakefront Vacation Home On The Chain Of Lakes In Winter Haven
2 5
apartment , Winter Haven
This lakefront houseboat on Winter Haven's Chain of Lakes offers stunning sunrise views, proximity to Winter Haven Municipal Airport and Brown's Seaplane Base, and easy access to LEGOLAND Florida and other theme parks. The three-bedroom, two-bathroom vessel sleeps five guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, a screened lanai, a backyard, Wi-Fi, air conditioning, smart TVs, and allows pets.
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 8 reviews
Winter Haven
06/20 – 06/27
$90/nighttotal: $630 (7 )
Vintage 1br Apartment Near Downtown Winter Haven
1 2
apartment , Winter Haven
This vintage apartment is located in a quiet residential area of Winter Haven, 1 mile from downtown, 4.3 miles from LEGOLAND Florida, and 2.5 miles from Chain of Lakes Park. This one-bedroom, one-bathroom rental sleeps up to three guests and features a kitchenette with a fridge, freezer, and microwave, plus air conditioning, internet, a shared garden, and parking.
Winter Haven
12/01 – 02/28
$142/nighttotal: $12638 (89 )
Walk To Winter Haven Hospital: Convenient Apt
1 2
apartment , Winter Haven
This apartment is situated in a prime Winter Haven district, 4 blocks from Winter Haven Hospital and 6 blocks from Downtown, with LEGOLAND Florida Resort 5 miles away. This 1100 square foot dwelling accommodates up to 2 guests and includes a full kitchen, free WiFi, on-site laundry, and mini-split A/C and heating.
9.9 299 reviews
Winter Haven
07/10 – 07/11
$177/nightfor 1 night
The Lake Alfred Citrus Wood Guest Cabin
1 4
cabin , Lake Alfred
This Lake Alfred guesthouse, near Interstate 4 and minutes from Winter Haven Municipal Airport, offers easy access to Legoland Florida (under 20 minutes), Walt Disney World, and Busch Gardens (45 minutes). The one-bedroom, one-bathroom cottage sleeps three, features a fully equipped kitchen, 50-inch HDTV with streaming services, 400 Mbps Wi-Fi, in-unit laundry, and a peaceful setting in the Green Swamp Forest with a private garden and parking.
9.0 13 reviews
Winter Haven
07/10 – 07/11
$182/nightfor 1 night
Private/spacious 1br Central Near Legoland 2 Miles
1 4
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.
10 2 reviews
Winter Haven
12/01 – 02/28
$132/nighttotal: $11748 (89 )
Charming 3-bedroom House In Tranquil Winter Haven W/lake Access
3 2
apartment , Winter Haven
This Winter Haven home is conveniently located a 4-minute drive from Indigo's Family Fun Center and Sertoma Park, offering easy access to LEGOLAND Florida and other area attractions. This 3-bedroom, 2-bathroom house sleeps 6 guests and features a fully equipped kitchen with microwave and dishwasher, in-house Wi-Fi, a smart TV, washer/dryer, and proximity to Circle B Bar Reserve and Chain of Lakes Park.
9.5 12 reviews
Winter Haven
07/10 – 07/11
$388/nightfor 1 night
The Best House
1 4
apartment , Winter Haven
This four-bedroom Winter Haven rental is situated in the Riverwood Circle neighborhood, approximately 10 minutes from LEGOLAND Florida Resort and Peppa Pig Theme Park, offering convenient access to the Chain of Lakes. The 4-bedroom, 3-bathroom house sleeps 10 guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, a swimming pool, fitness center, and free parking; enjoy nearby boating and jet skiing on the Chain of Lakes.
9.7 7 reviews
Winter Haven
06/25 – 06/29
$218/nighttotal: $872 (4 )
The Lake House Casita-legoland/chain Of Lakes/dock
1 5
apartment , Winter Haven
This canal-view casita in Winter Haven offers direct access to the Chain of Lakes and is located approximately 5 miles from LEGOLAND Florida Resort and 2 miles from downtown Winter Haven. This family-friendly vacation home accommodates up to 6 guests with 3 bedrooms, 1 bathroom, a full kitchen, air conditioning, and a screened lanai, providing ample space for relaxation and entertainment.
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.
9.6 4 reviews
Winter Haven
12/01 – 02/28
$221/nighttotal: $19669 (89 )
5 Br Home With Large Patio, Pool & Outdoor Family Fun - 7 Mins To Legoland!
5 2
apartment , Cypress Gardens
This five-bedroom Winter Haven vacation home, minutes from Cypress Gardens and a 7-8 minute drive from LEGOLAND Florida, offers easy access to area attractions and water sports. This 1910-square-foot rental boasts a private pool, a charcoal BBQ, sleeps 10-12 guests comfortably, and includes amenities such as a full kitchen, multiple bathrooms, and Smart TV.
8.3 1813 reviews
Winter Haven
06/20 – 06/27
$254/nighttotal: $1778 (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.
Winter Haven
07/10 – 07/11
$185/nightfor 1 night
Family Friendly 2br 1ba Close To Legoland
2 4
house , Cypress Gardens
This family-friendly 2 bedroom, 1 bathroom house is located in Winter Haven, just 1.8 miles from Legoland Florida and 6.8 miles from Swanns Railroad Station. This 1000 square foot residence accommodates up to 9 guests and features air conditioning, free WiFi, a kitchenette with a microwave, and free private parking, with a strict no-party policy.
10 15 reviews
Winter Haven
06/25 – 06/29
$246/nighttotal: $984 (4 )
The Modern Retreat By Legoland
1 5
apartment , Winter Haven
This four-bedroom, two-bathroom Winter Haven apartment rental is conveniently located seven minutes from LEGOLAND Florida. The family-friendly unit sleeps eight guests comfortably and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus amenities like air conditioning, parking, and internet access; a crib and double stroller are also provided.
Best Winter Haven vacation rentals with parking
8.6 8 reviews
Winter Haven
06/25 – 06/29
$162/nighttotal: $648 (4 )
3bed 2bath Spacious-lakehomeaceloc4mileslegoland
3 5
house , Winter Haven
This Cypress Gardens lake house in Winter Haven, Florida, is 4.1 miles from Legoland Florida and within 14 miles of several train stations. This 1,650-square-foot home features a spacious 3-bedroom, 2-bathroom layout, accommodating up to 13 guests, and includes amenities such as a fully equipped kitchen, in-unit laundry, free Wi-Fi, and private parking.
Winter Haven
06/25 – 06/29
$324/nighttotal: $1296 (4 )
White Door House!
1 5
house , Winter Haven
White Door House, a vacation rental in Winter Haven, is located 6.2 miles from Legoland Florida and 2.1 miles from Swanns Railroad Station (Historical). This 1800 square foot house accommodates up to 15 guests with 1 bedroom, 2 bathrooms, a full kitchen, and complimentary WiFi, with free private parking available.
Winter Haven
06/20 – 06/27
$183/nighttotal: $1281 (7 )
Charming And Cozy Winter Haven Oasis
1 2
apartment , Winter Haven
This 1-bedroom condo in Winter Haven is located a short distance from Bok Tower Gardens and Northgate Shopping Center. This 500 square feet unit accommodates up to 4 guests with a queen bed and a sofa bed, offering air conditioning, heating, internet, and 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.
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?
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?
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?
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?
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.
10 3 reviews
Winter Haven
06/25 – 06/29
$275/nighttotal: $1100 (4 )
South Facing Villa - Modern Finishes
4 5
apartment , Haines City
This Haines City vacation home is located a 15-minute walk from Southern Dunes Golf Club and Country Club, and within 6 miles of a regional medical center and Ember Dog Park. This 1,540-square-foot property boasts four bedrooms, three bathrooms, a private pool, barbecue grills, and accommodates up to eight guests, offering a fully equipped kitchen and in-house laundry facilities.
Winter Haven
06/25 – 06/29
$250/nighttotal: $1000 (4 )
Golf Course Views, Southern Dunes Pool Villa, Large Pool Deck
3 5
apartment , Haines City
This Haines City vacation home is located within a 15-minute walk of Southern Dunes Golf Club and Country Club, and a short 3-mile drive from Ember Dog Park. This 1740-square-foot property features three bedrooms, two bathrooms, a private pool, and can comfortably accommodate six guests, boasting a fully equipped kitchen, laundry facilities, and a balcony overlooking the garden.
9.5 13 reviews
Winter Haven
07/10 – 07/11
$279/nightfor 1 night
Getaway Clubhouse
3 4
house , Winter Haven
This Winter Haven vacation home is ideally situated 5 miles from LEGOLAND Florida and 5 miles from downtown Winter Haven, offering easy access to major attractions and convenient proximity to multiple railroad stations. This 1610-square-foot house features three bedrooms, two bathrooms, and accommodates up to 15 guests, boasting a fully equipped kitchen, free Wi-Fi, air conditioning, and a relaxing garden.
9.4 28 reviews
Winter Haven
06/20 – 06/27
$180/nighttotal: $1260 (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.
Best Winter Haven vacation rentals with air conditioning
8.4 31 reviews
Winter Haven
06/25 – 06/29
$281/nighttotal: $1124 (4 )
Spacious 4-bedroom 2-bath Abode
4 5
house , Winter Haven
This 4-bedroom home is conveniently located in Winter Haven, Florida, just a short drive from Swanns Railroad Station and Legoland Florida. The property has received excellent ratings for user experience, location, and cleanliness. This spacious home offers 2,300 square feet of living space, perfect for families or groups. The property features a fully equipped kitchen, private parking, free Wi-Fi, a patio and garden, and air conditioning.
9.7 103 reviews
Winter Haven
12/01 – 02/28
$69/nighttotal: $6141 (89 )
1 Comfy & Cozy Cottage - Unit 18
1 2
apartment , Cypress Gardens
This cozy cottage is located on a private canal leading to Lake Eloise, just a short drive from Legoland and Disney World, offering a peaceful escape near the action. The cottage has received excellent ratings for location, cleanliness, and overall experience. The cottage features one bedroom and one bathroom, accommodating up to four guests comfortably. Enjoy amenities like a fully equipped kitchen, air conditioning, a private garden, and access to the canal for fishing and water activities.
This 3-bedroom apartment is located on a private 3-acre lakefront property just 2 miles from downtown Winter Haven and 4 miles from LEGOLAND. It has excellent user, location, and cleanliness ratings. The apartment has 2 full bathrooms and can accommodate up to 7 guests. It features a fully equipped kitchen, a laundry room, and a private porch and yard. Guests can enjoy complimentary Wi-Fi, Roku Smart TVs with streaming services, and access to outdoor amenities like designated parking and a garden.
10 2 reviews
Winter Haven
12/01 – 02/28
$133/nighttotal: $11837 (89 )
Cozy 1-bedroom Retreat Near Downtown & Legoland
1 2
apartment , Winter Haven
This Winter Haven apartment rental is minutes from downtown, LEGOLAND Florida, and a hospital, offering easy highway access and a 45-minute drive to Walt Disney World. The one-bedroom, one-bathroom unit sleeps two guests and features a small kitchenette with a mini-fridge, microwave, and electric hot plate, plus convenient proximity to Indigo's Family Fun Center and Willowbrook Golf Course.