The 10 best vacation homes in Winter Haven, US | Booking.com
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Vacation Homes in Winter Haven

Find the vacation homes that appeal to you the most

The best vacation homes in Winter Haven

Check out our selection of great vacation homes in Winter Haven

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Getaway Clubhouse

Winter Haven

Getaway Clubhouse is located in Winter Haven, just 4.3 miles from Legoland Florida and 8.7 miles from Phosmico Railroad Station (Historical). This vacation home offers accommodations with a balcony.

A
Anna B
From
United States
Very clean! Very convenient to our convention. We had everything we needed. I would definitely stay there again!
Scored out of 10, guest rating 10.0
Exceptional - What previous guests thought, 8 reviews
Location 9.3
Price from
$143
1 night, 2 adults
Check availability

Large 3Bedrooms 1 Bath Near DownTown Dining

Winter Haven

Large 3Bedrooms 1 Bath Near DownTown Dining is located in Winter Haven, just 3.8 miles from Legoland Florida and 3.9 miles from Swanns Railroad Station (Historical).

K
Kim
From
United States
Great location for softball tournament in Winter Haven! Hosts were very kind and attentive
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 9 reviews
Location 9.0
Price from
$135
1 night, 2 adults
Check availability

Lakeside Lofts at Lake Martha

Winter Haven

Lakeside Lofts at Lake Martha offers accommodations in Winter Haven, 4.5 miles from Legoland Florida and 10 miles from Phosmico Railroad Station (Historical).

d
daniel
From
United States
A great property to stay with family near Lego Land. This trumps staying at a hotel. We had the whole place to ourselves on a quiet street. It’s near local shops and downtown area. The home is updated with all amnesties included. The owner was polite and attentive. Everything I asked him he messaged me right away. A++++ we will be surely rebooking in the future. Thank you!!
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 16 reviews
Location 9.3
Price from
$182.16
1 night, 2 adults
Check availability

Peaceful Lakeside Retreat

Winter Haven

Providing a garden, Peaceful Lakeside Retreat provides accommodations in Winter Haven. This vacation home features free private parking, a 24-hour front desk, and free Wifi.

B
Brian
From
United States
So peaceful relaxing on the dock by the lake. Awesome location.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 7 reviews
Location 9.6
Price from
$183
1 night, 2 adults
Check availability

Stylish-N-Private 1BR Retreat 2 Miles to LegoLand

Winter Haven

Stylish-N-Private 1BR Retreat 2 Miles to LegoLand offers accommodations in Winter Haven, 11 miles from Phosmico Railroad Station (Historical) and 12 miles from Conshul Railroad Station.

A
Alexia
From
United States
The place was very cute, clean, and perfect for our family of three. The owners were very responsive and helped us quickly if we needed anything. A very great stay!
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 13 reviews
Location 9.1
Price from
$80.19
1 night, 2 adults
Check availability

Groovy Funhouse Getaway - 4 bdrm near Legoland

Winter Haven

Groovy Funhouse Getaway - 4 bdrm near Legoland is a recently renovated vacation home in Winter Haven where guests can make the most of its outdoor swimming pool, garden, and barbecue facilities.

S
Skelton
From
Abkhazia
I love the set up it was very clean colorful and they everything we needed as of we lived there
Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 31 reviews
Location 7.0
Price from
$193.50
1 night, 2 adults
Check availability

Stylish Lake home with HUGE POOL, Arcade with PS5,and Theater Just 5 min from Legoland

Winter Haven

Stylish Lake home with HUGE POOL, Arcade with PS5, and Theater Just 5 min from Legoland offers accommodations in Winter Haven, 2.3 miles from Legoland Florida and 6.2 miles from Swanns Railroad...

A
Anna
From
United States
The owner is extremely responsive and communicative, and she goes as far as she needs to, to ensure comfort and happiness. We had absolutely amazing time. The house is really well set up. There is everything you need to entertain your kids. The game room, the movie theatre room and the pool. The house is on the lake with absolutely adorable view! The whole house is beautifully staged and decorated. Very comfortable to sleep in, cook if you need to, and enjoy your family time. Great experience! Definitely recommending. Everything was amazing! This is true little treasure. The house, the little lake view, the host. You will not be disappointed in a stay here. Highly recommending!
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 11 reviews
Location 8.5
Price from
$359.10
1 night, 2 adults
Check availability

Cozy Lakefront Home w/ Pool -7 mins from Legoland

Winter Haven

Cozy Lakefront Home w/ Pool -7 mins from Legoland is located in Winter Haven, just 2.3 miles from Legoland Florida and 6 miles from Swanns Railroad Station (Historical).

R
Reyes
From
United States
The location was 6 mins from Legoland, place was beautiful, incredibly comfortable, and the host was so kind and responsive. I can't rave enough about this place. Forget staying on Legoland property this was way way way better.
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 8 reviews
Location 9.6
Price from
$237.50
1 night, 2 adults
Check availability

2Bed 1Bath CentralLocation 2 Mile LEGOLAND and Dining

Cypress Gardens (Near Winter Haven)

2Bed 1Bath CentralLocation 2 Mile LEGOLAND and Dining offers accommodations in Cypress Gardens, 7.1 miles from Swanns Railroad Station (Historical) and 11 miles from Phosmico Railroad Station...

K
Kurtis
From
United States
Great experience. It was nice and had everything needed for a one night stay. Would definitely book again and share info with friends
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 5 reviews
Location 10.0
Price from
$108
1 night, 2 adults
Check availability

Adams Estate

Lake Alfred (Near Winter Haven)

Offering pool with a view, Adams Estate provides accommodations in Lake Alfred. There's a private entrance at the vacation home for the convenience of those who stay.

d
david
From
United States
Clean and location was great for our golf trip. Bottled water ,coffee and snack basket were great !!
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 10 reviews
Location 9.6
Price from
$229
1 night, 2 adults
Check availability
All vacation homes in Winter Haven

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Winter Haven and surrounding area in the past month

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Save money on vacation homes in Winter Haven and nearby – budget options available

  • Scored out of 10, guest rating 8.1
    Very Good - What previous guests thought, 6 reviews

    3Bed 2Bath Spacious-LakeHomeAceLoc4milesLEGOLAND offers accommodations in Cypress Gardens, 4.4 miles from Legoland Florida and 4.9 miles from Swanns Railroad Station (Historical).

  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 5 reviews

    2Bed 1Bath CentralLocation 2 Mile LEGOLAND and Dining offers accommodations in Cypress Gardens, 7.1 miles from Swanns Railroad Station (Historical) and 11 miles from Phosmico Railroad Station (...

  • Cozy Bungalow

    Winter Haven
    Budget options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Cozy Bungalow offers accommodations in Winter Haven, 4.3 miles from Legoland Florida and 8.7 miles from Phosmico Railroad Station (Historical).

  • Lake Silver Retreat lll

    Winter Haven
    Budget options available

    Lake Silver Retreat lll is located in Winter Haven, just 10 miles from Carters Railroad Station and 11 miles from Tanco Railroad Station.

  • Lake Silver V - Lake House with Dock - Legoland Getaway! is located in Winter Haven, just 2.6 miles from Swanns Railroad Station (Historical) and 5.2 miles from Legoland Florida.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    6 Mi to Legoland Retreat with Pool and Fenced Yard is located in Winter Haven, just 3.1 miles from Swanns Railroad Station (Historical) and 5.8 miles from Legoland Florida.

  • Emerald Anchor Escape

    Winter Haven
    Budget options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Emerald Anchor Escape offers accommodations in Winter Haven, 3.7 miles from Swanns Railroad Station (Historical) and 6.1 miles from Legoland Florida. Guests may go for a swim in the private pool.

  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 3 reviews

    Lanai and Pool Elegant Villa in Winter Haven! offers accommodations in Winter Haven, 3.3 miles from Swanns Railroad Station (Historical) and 6.4 miles from Legoland Florida.

Great access to the city center. Check these vacation homes in Winter Haven and nearby

  • Otis Sunrise Villa offers accommodations in Winter Haven, 4 miles from Legoland Florida and 4.3 miles from Swanns Railroad Station (Historical).

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    6.4 miles from Legoland Florida in Winter Haven, Lakefront Winter Haven Retreat Hot Tub and Patio! provides accommodations with access to a hot tub.

  • 4 Mi to Legoland Poolside Paradise! is located in Winter Haven, just 4.7 miles from Swanns Railroad Station (Historical) and 8.6 miles from Phosmico Railroad Station (Historical).

  • Waterfront Vacation Rental on Lake Mirror! offers accommodations in Winter Haven, 8.2 miles from Carters Railroad Station and 10 miles from Phosmico Railroad Station (Historical).

  • Serene Lake Views Winter Haven Home is located in Winter Haven, just 6.9 miles from Legoland Florida and 8.2 miles from Carters Railroad Station.

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 11 reviews

    Hook, Line and Leisure Lakefront Gem, 2 Mi to Dtwn is located in Winter Haven, just 9.4 miles from Carters Railroad Station and 11 miles from Phosmico Railroad Station (Historical).

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    5 miles from Swanns Railroad Station (Historical) in Winter Haven, Waterfront Winter Haven Home with Dock and Hot Tub! provides accommodations with access to a hot tub.

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 11 reviews

    Winter Haven Home with Pool Near Legoland! offers accommodations in Winter Haven, 2.8 miles from Legoland Florida and 5.3 miles from Swanns Railroad Station (Historical).

Enjoy breakfast in Winter Haven and nearby

  • Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 8 reviews

    Cozy Lakefront Home w/ Pool -7 mins from Legoland is located in Winter Haven, just 2.3 miles from Legoland Florida and 6 miles from Swanns Railroad Station (Historical).

  • Scored out of 10, guest rating 8.0
    Very Good - What previous guests thought, 11 reviews

    Stylish Lake home with HUGE POOL, Arcade with PS5, and Theater Just 5 min from Legoland offers accommodations in Winter Haven, 2.3 miles from Legoland Florida and 6.2 miles from Swanns Railroad...

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 7 reviews

    Bright Cypress Gardens Home Near Legoland! is located in Cypress Gardens, just 12 miles from Dearborn Railroad Station and 13 miles from Tanco Railroad Station.

  • Scored out of 10, guest rating 8.0
    Very Good - What previous guests thought, 15 reviews

    Spacious 4-bedroom 2-bath Abode is located in Winter Haven, just 7.7 miles from Legoland Florida and 7.9 miles from Phosmico Railroad Station (Historical).

  • Lake Lulu Escape offers accommodations in Winter Haven, 2.9 miles from Legoland Florida and 5.6 miles from Swanns Railroad Station (Historical).

  • Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 6 reviews

    Winter Haven Retreat with Private Pool! offers accommodations in Winter Haven, 2.1 miles from Legoland Florida and 6 miles from Swanns Railroad Station (Historical).

  • Sunrise on Lake Idylwild is located in Winter Haven, just 8.9 miles from Tanco Railroad Station and 9 miles from Elmer Railroad Station.

  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 3 reviews

    Providing a garden, Modern 3 Bed 2 Bath Home 3 minutes from Legoland features accommodations in Winter Haven. This vacation home provides air-conditioned accommodations with a patio.

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Hotels in Winter Haven

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