Skip to main content

Holiday Homes in Winter Haven

Find the holiday homes that appeal to you the most

The best holiday homes in Winter Haven

Check out our pick of great holiday homes in Winter Haven

Filter by:

Review score

BlockHaven near Legoland, Disney

Winter Haven

BlockHaven near Legoland, Disney is a recently renovated holiday home in Winter Haven, where guests can make the most of its garden and barbecue facilities.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
Price from
US$184.92
1 night, 2 adults

Kid-friendly Home w Pool & BBQ

Winter Haven

Located in Winter Haven, Kid-friendly Home w Pool & BBQ provides accommodation with private pool, free WiFi and free private parking for guests who drive.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 5 reviews
Price from
US$170
1 night, 2 adults

Getaway Clubhouse

Winter Haven

Set in Winter Haven, 5.6 km from Swanns Railroad Station (Historical) and 7 km from Legoland Florida, Getaway Clubhouse offers air-conditioned accommodation with a balcony and free WiFi.

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 10 reviews
Price from
US$143
1 night, 2 adults

Peaceful Lakeside Retreat

Winter Haven

Situated in Winter Haven, 7.1 km from Swanns Railroad Station (Historical) and 10 km from Legoland Florida, Peaceful Lakeside Retreat offers a garden and air conditioning.

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 7 reviews
Price from
US$210
1 night, 2 adults

Cozy Lakefront Home w/ Pool -7 mins from Legoland

Winter Haven

Boasting air-conditioned accommodation with a private pool, lake view and a patio, Cozy Lakefront Home w/ Pool -7 mins from Legoland is situated in Winter Haven.

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 8 reviews
Price from
US$237.50
1 night, 2 adults

Adams Estate

Lake Alfred (Near Winter Haven)

Set in Lake Alfred, Adams Estate provides a private pool. There is a private entrance at the holiday home for the convenience of those who stay.

D
Daniel
From
United Kingdom
Clean, spacious and had all the amenities
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 10 reviews
Price from
US$245
1 night, 2 adults

3Bed 2Bath Spacious-LakeHomeAceLoc4milesLEGOLAND

Cypress Gardens (Near Winter Haven)

Situated in Cypress Gardens, 7 km from Legoland Florida and 7.9 km from Swanns Railroad Station (Historical), 3Bed 2Bath Spacious-LakeHomeAceLoc4milesLEGOLAND features spacious air-conditioned...

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 6 reviews
Price from
US$112.50
1 night, 2 adults

Slice of Paradise 2.0- Golf Course View Villa

Haines City (Near Winter Haven)

Featuring air-conditioned accommodation with a private pool, Slice of Paradise 2.0- Golf Course View Villa is located in Haines City.

E
ELIZABETH
From
United Kingdom
Well located. Like that there is security at the entrance. The house was lovely with lots of homely touches. Has everything you might need. I managed to leave something behind, but no problem, it is being sent to me in the uk! Fantastic service.😍
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 6 reviews
Price from
US$135.95
1 night, 2 adults

Brand New Home by LegoLandPeppa Pig Park!

Lake Wales (Near Winter Haven)

Set in Lake Wales, 11 km from Legoland Florida and 24 km from Swanns Railroad Station (Historical), Brand New Home by LegoLandPeppa Pig Park! offers air conditioning.

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 10 reviews
Price from
US$256.50
1 night, 2 adults

Canterbury Oasis

Haines City (Near Winter Haven)

Located 19 km from Swanns Railroad Station (Historical), Canterbury Oasis offers accommodation with a patio, as well as a garden and a bar.

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 7 reviews
Price from
US$130.50
1 night, 2 adults
All holiday homes in Winter Haven

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes in Winter Haven and surroundings in the past month

See all

Popular with guests booking holiday homes in Winter Haven

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 7 reviews

Popular with guests booking holiday homes in Winter Haven

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 4 reviews

Popular with guests booking holiday homes in Winter Haven

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 10 reviews

Popular with guests booking holiday homes in Winter Haven

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

Popular with guests booking holiday homes in Winter Haven

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 17 reviews

Popular with guests booking holiday homes in Winter Haven

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews

Popular with guests booking holiday homes in Winter Haven

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews

Popular with guests booking holiday homes in Winter Haven

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 14 reviews

Popular with guests booking holiday homes in Winter Haven

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 10 reviews

Enjoy breakfast in Winter Haven and nearby

Cozy Bungalow

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

Set in Winter Haven, 5.6 km from Swanns Railroad Station (Historical) and 7 km from Legoland Florida, Cozy Bungalow offers spacious air-conditioned accommodation with a balcony and free WiFi.

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

Set in Winter Haven, 4.9 km from Swanns Railroad Station (Historical) and 9.3 km from Legoland Florida, 6 Mi to Legoland Retreat with Pool and Fenced Yard offers spacious air-conditioned accommodation...

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

3.6 km from Swanns Railroad Station (Historical), Historic home lake access, near parks and venues is a recently renovated property located in Winter Haven and provides air-conditioned rooms with free...

From US$295.98 per night
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 3 reviews

Set in Winter Haven, 5.4 km from Swanns Railroad Station (Historical), Lanai and Pool Elegant Villa in Winter Haven!

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

Located in Winter Haven, 5.3 km from Swanns Railroad Station (Historical) and 10 km from Legoland Florida, Lakefront Winter Haven Retreat Hot Tub and Patio! offers air conditioning.

Situated in Winter Haven, 5.3 km from Legoland Florida and 7.5 km from Swanns Railroad Station (Historical), 4 Mi to Legoland Poolside Paradise!

Located in Winter Haven, 11 km from Legoland Florida and 13 km from Carters Railroad Station, Waterfront Vacation Rental on Lake Mirror! offers air conditioning.

Located in Winter Haven, 11 km from Legoland Florida and 13 km from Carters Railroad Station, Serene Lake Views Winter Haven Home offers air conditioning.

Great access to the city centre. Check these holiday homes in Winter Haven and nearby

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

Featuring air-conditioned accommodation with a heated pool, Waterfront Winter Haven Home with Dock and Hot Tub! is located in Winter Haven.

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

Boasting air-conditioned accommodation with a private pool, lake view and a patio, Cozy Lakefront Home w/ Pool -7 mins from Legoland is situated in Winter Haven.

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

Situated in Winter Haven in the Florida region, Spacious 4-bedroom 2-bath Abode features a patio.

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

Set in Winter Haven, 3.4 km from Legoland Florida and 10 km from Swanns Railroad Station (Historical), Winter Haven Retreat with Private Pool!

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 14 reviews

Stylish-N-Private 1BR Retreat 2 Miles to LegoLand is set in Winter Haven, 19 km from Conshul Railroad Station, 21 km from Dearborn Railroad Station, and 23 km from Tanco Railroad Station.

From US$159.27 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 4 reviews

Featuring air-conditioned accommodation with a patio, Modern 3 Bed 2 Bath Home 3 minutes from Legoland is set in Winter Haven. Located 1.6 km from Legoland Florida, the property provides a garden.

Boasting garden views, Luxury 3BR with Private POOL & GAME ROOM, only 4 MIN to LEGOLAND features accommodation with a bar and a patio, around 3.6 km from Legoland Florida.

Situated in Winter Haven, 2.7 km from Legoland Florida and 14 km from Swanns Railroad Station (Historical), Lakefront Retreat In Winterset offers air conditioning. A hot tub is available for guests.

Save money on holiday 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

Situated in Cypress Gardens, 7 km from Legoland Florida and 7.9 km from Swanns Railroad Station (Historical), 3Bed 2Bath Spacious-LakeHomeAceLoc4milesLEGOLAND features spacious air-conditioned...

From US$220.41 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 7 reviews

2Bed 1Bath CentralLocation 2 Mile LEGOLAND and Dining is situated in Cypress Gardens, 17 km from Phosmico Railroad Station (Historical), 19 km from Conshul Railroad Station, as well as 21 km from...

From US$192.36 per night

<h2>Spacious Accommodation</h2> Pool 9min Legoland Disney Universal 40 Min in Cypress Gardens offers a spacious holiday home with three bedrooms and two bathrooms.

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, 10 km from Swanns Railroad Station (Historical), 15 km from Phosmico Railroad Station (Historical), and 17 km from Conshul...

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 7 reviews

Situated in Auburndale, 10 km from Carters Railroad Station and 11 km from Swanns Railroad Station (Historical), Lake Views and Private Porch Auburndale Family Home features air-conditioned...

Adams Estate

Lake Alfred
Budget options available
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 10 reviews

Set in Lake Alfred, Adams Estate provides a private pool. There is a private entrance at the holiday home for the convenience of those who stay.

From US$557.76 per night
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 4 reviews

Situated in Winter Haven in the Florida region, Serene Lakeside Retreat- 3 Bdr Romantic Getaway features a patio. Guests can benefit from a balcony and a picnic area.

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review

Set in Winter Haven, 5.8 km from Legoland Florida and 17 km from Swanns Railroad Station (Historical), Playground Access Winter Haven Getaway with Patio!

Holiday Homes with swimming pools in Winter Haven and nearby

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 3 reviews

Set in Winter Haven, 4.9 km from Legoland Florida and 17 km from Swanns Railroad Station (Historical), The Luxury Lakehouse offers air conditioning.

FAQ about holiday homes in Winter Haven