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, (3 reviews)
"Great location. Great communication with host. "
United States
Reid
The price is R$ 297
R$ 1.245 total
includes taxes & fees
1 May - 2 May
BlockHaven near Legoland & Disney

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 R$ 833
R$ 2.143 total
includes taxes & fees
4 May - 5 May
Large Family Home, Legoland, Pet Friendly, 7 Beds

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, (31 reviews)
"Great communication with the host , house was clean and has lots of room to spread out. We enjoyed our stay. The park across the street had loud music playing at night which isn’t the host’s fault. Coffee bar was well stocked and kitchen is very nice. "
United States
Seth L.
The price is R$ 989
R$ 2.370 total
includes taxes & fees
4 May - 5 May
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events

Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!

Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
Winter Haven
10.0 out of 10, Exceptional, (53 reviews)
"It was pet friendly. "
United States
Ibia
The price is R$ 827
R$ 1.887 total
includes taxes & fees
3 May - 4 May
Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!

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, (3 reviews)
"Great get away for 2! Perfect size. Very clean and nicely decorated. The host was very responsive. Highly recommend this property. "
United States
Anonymous traveler
The price is R$ 550
R$ 939 total
includes taxes & fees
7 May - 8 May
Cozy 1 bedroom home in Winter Haven perfect for your getaway.

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Cheerful 4 Bed, 3 Bath Home with Screened Pool
Winter Haven
9.8 out of 10, Exceptional, (27 reviews)
"Excellent location, house was immaculate and beautiful. We stayed over xmas and there was even a tree for us. Highly recommend this place and would stay here again. "
United States
Eli R.
The price is R$ 924
R$ 2.161 total
includes taxes & fees
4 May - 5 May
Cheerful 4 Bed, 3 Bath Home with Screened Pool

Private/Spacious 1BR Central Near LegoLand 2 Miles

Private/Spacious 1BR Central Near LegoLand 2 Miles
Winter Haven
9.2 out of 10, Wonderful, (12 reviews)
"clean room"
United States
sandra
The price is R$ 405
R$ 861 total
includes taxes & fees
1 May - 2 May
Private/Spacious 1BR Central Near LegoLand 2 Miles

Large 3/1 Near DownTown and Dining

Large 3/1 Near DownTown and Dining
Winter Haven
7.2 out of 10, Good, (13 reviews)
"Clean, quiet and comfortable beds. "
United States
Jason
The price is R$ 645
R$ 1.272 total
includes taxes & fees
3 May - 4 May
Large 3/1 Near DownTown and Dining

The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia
Winter Haven
9.8 out of 10, Exceptional, (14 reviews)
"Nice location, comfortable stay."
United States
Karthik D.
The price is R$ 600
R$ 1.486 total
includes taxes & fees
3 May - 4 May
The Old Haven - An Enduring Piece of Nostalgia

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
9.8 out of 10, Exceptional, (6 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 R$ 532
R$ 1.549 total
includes taxes & fees
1 May - 2 May
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

Spacious 4-bedroom house in pleasant Winter Haven with AC

Spacious 4-bedroom house in pleasant Winter Haven with AC
Winter Haven
9.6 out of 10, Exceptional, (4 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 R$ 810
R$ 2.276 total
includes taxes & fees
5 May - 6 May
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, (12 reviews)
"Great location, clean and great communication with hosts "
United States
Angie Y.
The price is R$ 625
R$ 1.557 total
includes taxes & fees
3 May - 4 May
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

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)
"Everything was very clean! "
United States
Emilly D.
The price is R$ 814
R$ 1.316 total
includes taxes & fees
4 May - 5 May
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

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 R$ 247
R$ 1.339 total
includes taxes & fees
1 May - 2 May
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 R$ 625
R$ 1.453 total
includes taxes & fees
3 May - 4 May
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, (5 reviews)
"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.
The price is R$ 758
R$ 2.457 total
includes taxes & fees
4 May - 5 May
Family Friendly Lake House W/ Pool Near 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, (10 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 R$ 715
R$ 1.713 total
includes taxes & fees
13 May - 14 May
Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes

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, (3 reviews)
"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 R$ 1.748
R$ 5.046 total
includes taxes & fees
27 May - 28 May
Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17

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

Charming 7-Bedroom Estate with AC & Resort-Style Pool – Winter Haven
Winter Haven
7.6 out of 10, Good, (5 reviews)
"Great for large families to gather in stay."
United States
Christopher S.
The price is R$ 2.024
R$ 4.765 total
includes taxes & fees
4 May - 5 May
Charming 7-Bedroom Estate with AC & Resort-Style Pool – Winter Haven

Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds
Winter Haven
10.0 out of 10, Exceptional, (6 reviews)
"Great welcoming and answered every question I had. Highly recommend this lovely cottage. "
United States
Kristofer G.
The price is R$ 539
R$ 1.208 total
includes taxes & fees
4 May - 5 May
Modern Comfort, Pet Friendly, 2 King Beds
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
202
Accommodation
23135 Vacation Homes
Lowest Price
R$ 861
Highest Price
R$ 5.046