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 AED 141
AED 828 total
includes taxes & fees
31 May - 1 Jun
BlockHaven near Legoland & Disney

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 AED 404
AED 691 total
includes taxes & fees
18 May - 19 May
Cozy 1 bedroom home in Winter Haven perfect for your getaway.

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 AED 613
AED 1,520 total
includes taxes & fees
18 May - 19 May
Large Family Home, Legoland, Pet Friendly, 7 Beds

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 AED 545
AED 1,302 total
includes taxes & fees
18 May - 19 May
Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!

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, (28 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 AED 680
AED 1,585 total
includes taxes & fees
18 May - 19 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 AED 298
AED 633 total
includes taxes & fees
18 May - 19 May
Private/Spacious 1BR Central Near LegoLand 2 Miles

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 AED 441
AED 1,092 total
includes taxes & fees
18 May - 19 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 AED 329
AED 1,044 total
includes taxes & fees
21 May - 22 May
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

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, (32 reviews)
"The host was very attentive, and responsive to our questions and comments. "
United States
Matt O.
The price is AED 727
AED 1,753 total
includes taxes & fees
24 May - 25 May
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events

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)
"Very clean, welcoming home, close to the Wedding Venue 650. Close to Legoland as well. Host was very kind and accommodating. Will definitely stay again when going to this area!!"
United States
Cheryl G.
The price is AED 459
AED 1,111 total
includes taxes & fees
17 Jun - 18 Jun
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 AED 585
AED 960 total
includes taxes & fees
18 May - 19 May
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

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 AED 544
AED 1,597 total
includes taxes & fees
18 May - 19 May
Spacious 4-bedroom house in pleasant Winter Haven with AC

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 AED 248
AED 1,058 total
includes taxes & fees
18 May - 19 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 AED 459
AED 1,046 total
includes taxes & fees
18 May - 19 May
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Legoland & Lakes Pool Home | Pet Friendly

Legoland & Lakes Pool Home | Pet Friendly
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay in Winterhaven, Florida. The house was so spacious and beautifully decorated. We had everything we could need. The pool is amazing. The home owner was very attentive and a pleasure to work with. We will come back."
United States
Julie
The price is AED 522
AED 2,030 total
includes taxes & fees
20 May - 21 May
Legoland & Lakes Pool Home | Pet Friendly

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 AED 525
AED 1,207 total
includes taxes & fees
18 May - 19 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, (4 reviews)
"Great home with lots of room and things to do. Everything was easy and we love staying here!"
United States
Megan D.
The price is AED 1,265
AED 3,683 total
includes taxes & fees
20 May - 21 May
Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17

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 AED 26,446
AED 33,622 total
includes taxes & fees
25 May - 26 May
Family Friendly Lake House W/ Pool Near Legoland

Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds
Winter Haven
10.0 out of 10, Exceptional, (7 reviews)
"Great welcoming and answered every question I had. Highly recommend this lovely cottage. "
United States
Kristofer G.
The price is AED 396
AED 891 total
includes taxes & fees
19 May - 20 May
Modern Comfort, Pet Friendly, 2 King Beds

Kissimmee Retreat with Jacuzzi and Games

Kissimmee Retreat with Jacuzzi and Games
Kissimmee
The price is AED 343
AED 870 total
includes taxes & fees
18 May - 19 May
Kissimmee Retreat with Jacuzzi and Games
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