Search Vacation Homes in Winter Haven

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winter Haven vacation homes

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"House was great, perfect central location. Very quiet neighborhood nice farm outside peaceful back yard seating area. "
United States
Wade
The price is ¥12,741
¥43,073 total
includes taxes & fees
Mar 11 - Mar 12
BlockHaven near Legoland & Disney

Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events

Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Winter Haven
9.8 out of 10, Exceptional, (28 reviews)
"Awesome look forward to future stay "
United States
cheryl d.
The price is ¥32,092
¥76,428 total
includes taxes & fees
Mar 16 - Mar 17
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events

Cozy 1 bedroom home in Winter Haven perfect for your getaway.

Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"Yes the dogs liked it and they enjoyed walking in the neighborhood."
United States
John W.
Cozy 1 bedroom home in Winter Haven perfect for your getaway.

Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful stay in Winter Haven for our family Legoland trip, including our dog!The house was spotless, cozy, and easily accommodated all of us.Close to the park, would definitely stay again."
United States
Oscar G.
The price is ¥17,495
¥48,120 total
includes taxes & fees
Mar 10 - Mar 11
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Heated Pool and Hot tub-near Legoland, Disney, Theme parks
Winter Haven
9.8 out of 10, Exceptional, (45 reviews)
"We had a great stay!"
United States
Harper B.
The price is ¥36,447
¥72,566 total
includes taxes & fees
Mar 31 - Apr 1
Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Cheerful 4 Bed, 3 Bath Home with Screened Pool
Winter Haven
10.0 out of 10, Exceptional, (24 reviews)
"Very lovely place to stay for a family vacation."
United States
Charley L.
The price is ¥37,078
¥76,902 total
includes taxes & fees
Mar 23 - Mar 24
Cheerful 4 Bed, 3 Bath Home with Screened Pool

Large Family Home, Legoland, Pet Friendly, 7 Beds

Large Family Home, Legoland, Pet Friendly, 7 Beds
Winter Haven
10.0 out of 10, Exceptional, (23 reviews)
"Everything was very nice and comfortable. "
United States
Gary B.
The price is ¥48,670
¥96,321 total
includes taxes & fees
Mar 22 - Mar 23
Large Family Home, Legoland, Pet Friendly, 7 Beds

Spacious 4-bedroom house in pleasant Winter Haven with AC

Spacious 4-bedroom house in pleasant Winter Haven with AC
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"An outstanding stay! The house was extremely clean, welcoming, and had all the amenities that made our family vacation unforgettable in our visit to Legoland park"
Mexico
Monica
The price is ¥28,716
¥75,236 total
includes taxes & fees
Mar 23 - Mar 24
Spacious 4-bedroom house in pleasant Winter Haven with AC

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Winter Haven
9.8 out of 10, Exceptional, (9 reviews)
"Great location, clean and great communication with hosts "
United States
Angie Y.
The price is ¥19,723
¥48,833 total
includes taxes & fees
Mar 22 - Mar 23
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia
Winter Haven
9.8 out of 10, Exceptional, (11 reviews)
"Home was charming and clean."
United States
Dave V.
The price is ¥18,934
¥46,609 total
includes taxes & fees
Mar 23 - Mar 24
The Old Haven - An Enduring Piece of Nostalgia

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Winter Haven
9.6 out of 10, Exceptional, (4 reviews)
"Wonderful home "
United States
Joshlynn
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

Large 3/1 Near DownTown and Dining

Large 3/1 Near DownTown and Dining
Winter Haven
7.4 out of 10, Good, (10 reviews)
"Clean, quiet and comfortable beds. "
United States
Jason
The price is ¥20,354
¥40,152 total
includes taxes & fees
Mar 22 - Mar 23
Large 3/1 Near DownTown and Dining

Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17

Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"Excellent property, rooms cleans, spacious. The game room beautifully. The backyard absolutely amazing. We give 20 starts to this property. Really recommend for a family trip, we enjoy our stay 100%"
United States
Mildrenys
The price is ¥53,658
¥157,446 total
includes taxes & fees
Mar 10 - Mar 11
Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17

BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!

BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"Awesome quiet and cozy place The host is very communicative and the house had everything we need"
United States
Patricia M.
The price is ¥10,366
¥44,675 total
includes taxes & fees
Mar 11 - Mar 12
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"Nice place very convenient for us. Would stay again"
United States
John G.
The price is ¥19,723
¥45,417 total
includes taxes & fees
Mar 9 - Mar 10
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Family Friendly Lake House W/ Pool Near Legoland

Family Friendly Lake House W/ Pool Near Legoland
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved our stay and highly recommend this home, especially for families! The house was clean, quiet, and spacious, featuring a well-stocked kitchen with high-quality cookware, multiple coffee makers, and kids' essentials. When we weren't at Legoland, we spent our time enjoying the heated salt-water pool, game room, and the dock for fishing and kayaking. Catching the sunrise over the lake was absolutely gorgeous. The hosts were incredibly friendly, flexible, and communicative--adding...
United States
Matthew B.
Family Friendly Lake House W/ Pool Near Legoland

Disney Castle Cove - Private Pool & Community Boat Ramp close to Legoland

Disney Castle Cove - Private Pool & Community Boat Ramp close to Legoland
Winter Haven
Disney Castle Cove - Private Pool & Community Boat Ramp close to Legoland

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

Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"The host was very accommodating and responsive. The house is clean, roomy, cute, and comfortable. There is so much to see and do in Winter Haven - I’ll return and stay at Rick’s Retreat again!"
United States
Mary R.
The price is ¥24,850
¥56,644 total
includes taxes & fees
Mar 21 - Mar 22
Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes

Charming 7-Bedroom Estate with AC & Resort-Style Pool – Winter Haven

Charming 7-Bedroom Estate with AC & Resort-Style Pool – Winter Haven
Winter Haven
8.0 out of 10, Very Good, (4 reviews)
"Great houseGreat location"
United States
Jose S.
The price is ¥71,001
¥159,358 total
includes taxes & fees
Mar 9 - Mar 10
Charming 7-Bedroom Estate with AC & Resort-Style Pool – Winter Haven
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Haven Hotel Reviews

Find out more about Winter Haven

Winter Haven Vacation Homes information

Number of reviews
147
Accommodation
24624 Vacation Homes
Lowest Price
¥40,152
Highest Price
¥159,358