A castle entrance with flags and banners, including a LEGO Kingdoms banner.

Search Holiday Homes in Winter Haven

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Winter Haven holiday homes

Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (6 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
The price is £177
includes taxes & fees
28 Jun - 29 Jun
BlockHaven near Legoland & Disney
Outdoor dining

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, (57 reviews)
"We really enjoyed our stay. Safe, quiet neighborhood, outdoor area was fantastic, beds were comfortable. Would stay again for sure. "
United States
Tara G.
The price is £262
includes taxes & fees
29 Jun - 30 Jun
Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
Smart TV

Large Family Home, Legoland, Pet Friendly, 7 Beds

Large Family Home, Legoland, Pet Friendly, 7 Beds
Winter Haven
10.0 out of 10, Exceptional, (24 reviews)
"Everything was very nice and comfortable. "
United States
Gary B.
The price is £322
includes taxes & fees
29 Jun - 30 Jun
Large Family Home, Legoland, Pet Friendly, 7 Beds
Fridge, microwave, oven, stovetop

3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724

3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
Winter Haven
9.4 out of 10, Exceptional, (67 reviews)
"The accommodation at this property was exceptional. It felt safe, and was safe Parking was great, proximity to dinning and shopping was withing 5 minutes drive, and the location was peaceful and safe."
United States
Dwight
The price is £201
includes taxes & fees
28 Jun - 29 Jun
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
Interior

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, (4 reviews)
"This is such a cozy 1 bedroom unit and the side yard was such a great bonus amenity."
United States
Christopher V.
The price is £145
includes taxes & fees
29 Jun - 30 Jun
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Living area

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 £201
includes taxes & fees
28 Jun - 29 Jun
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
Fridge, microwave, oven, stovetop

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, (33 reviews)
"The house was great!"
United States
Kristin H.
The price is £355
includes taxes & fees
29 Jun - 30 Jun
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Terrace/patio

The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia
Winter Haven
9.8 out of 10, Exceptional, (15 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
The price is £223
includes taxes & fees
28 Jun - 29 Jun
The Old Haven - An Enduring Piece of Nostalgia
4 bedrooms, free WiFi, bed sheets

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 £242
includes taxes & fees
28 Jun - 29 Jun
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
4 bedrooms, iron/ironing board, WiFi, bed sheets

White Door House!

White Door House!
Winter Haven
The price is £369
includes taxes & fees
14 Jul - 15 Jul
White Door House!
Fridge, microwave, oven, stovetop

Family Friendly Lake House W/ Pool Near Legoland

Family Friendly Lake House W/ Pool Near Legoland
Winter Haven
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful place! Perfect place to relax and close to all the Orlando attractions. "
United States
Brandon B.
The price is £401
includes taxes & fees
29 Jun - 30 Jun
Family Friendly Lake House W/ Pool Near Legoland
Dining

Hook, Line & Leisure: Lakefront Gem w/ Porch!

Hook, Line & Leisure: Lakefront Gem w/ Porch!
Florence Villa
9.6 out of 10, Exceptional, (29 reviews)
"The house is well updated and comfortable. Everything was very clean and well appointed. Kitchen well stocked for cooking and eating in. Lovely view of the lake from 2 bedrooms, living room and screened porch. Host was very responsive and checked in to see if we needed anything. Caretakers of property across street and also helpful and welcoming. Only 40-45 minutes from Disney. Was a good home base for our 12 day stay. Neighborhood generally quiet and friendly."
United States
Carolyn B.
The price is £297
includes taxes & fees
27 Jul - 28 Jul
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Fridge, microwave, oven, stovetop

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)
"Nice house for our stay."
United States
Debi K.
The price is £233
includes taxes & fees
28 Jun - 29 Jun
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Fridge, microwave, oven, stovetop

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 £221
includes taxes & fees
28 Jun - 29 Jun
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
TV

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, (11 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 £246
includes taxes & fees
28 Jun - 29 Jun
Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes
TV, fireplace

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 £318
includes taxes & fees
20 Jul - 21 Jul
Spacious 4-bedroom house in pleasant Winter Haven with AC
Fridge, microwave, oven, stovetop

3br Modern home w/hot tub>5min from LEGOLAND

3br Modern home w/hot tub>5min from LEGOLAND
Winter Haven
10.0 out of 10, Exceptional, (26 reviews)
"Great property!"
United States
Glenn C.
The price is £335
includes taxes & fees
28 Jun - 29 Jun
3br Modern home w/hot tub>5min from LEGOLAND
Smart TV, fireplace

The Love of my life.SmartHouse

The Love of my life.SmartHouse
Winter Haven
2.0 out of 10, (1 review)
The price is £192
includes taxes & fees
28 Jun - 29 Jun
The Love of my life.SmartHouse
Smart TV, fireplace

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 £212
includes taxes & fees
21 Jul - 22 Jul
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Interior

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 £915
includes taxes & fees
21 Jul - 22 Jul
Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Music in the pool"
Anaysi 3-night trip
Posted 1 hour ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Haven

Winter Haven Holiday Homes information

Number of reviews
199
Accommodation
23171 Holiday Homes
Lowest Price
£145
Highest Price
£915