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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winter Haven holiday homes

A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

1. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (7 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 £182
includes taxes & fees
30 Sept - 1 Oct
BlockHaven near Legoland & Disney
A modern living room with a grey sofa, a dining area with a round table and chairs, a kitchen with white cabinets, a clock, and a decorative wall piece.

2. 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 £146
includes taxes & fees
4 Oct - 5 Oct
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
A modern kitchen with a stainless steel refrigerator, white cabinetry, a double sink, and a painting of flowers on the wall.

3. New Haven 5 mi to Legoland & 0.5 mi to dwntwn

New Haven 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
10.0 out of 10, Exceptional, (1 review)
The price is £212
includes taxes & fees
29 Sept - 30 Sept
New Haven 5 mi to Legoland & 0.5 mi to dwntwn
A living room with a grey sofa, a wooden coffee table, a patterned rug, a TV, and a wall mural of underwater scenes.

4. 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 £219
includes taxes & fees
1 Oct - 2 Oct
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
A wooden house with a porch, steps, and a fenced area with plants.

5. 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 £228
includes taxes & fees
29 Sept - 30 Sept
The Old Haven - An Enduring Piece of Nostalgia
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

6. Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Winter Haven
9.8 out of 10, Exceptional, (13 reviews)
"Nice house for our stay."
United States
Debi K.
The price is £243
includes taxes & fees
29 Sept - 30 Sept
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

7. 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, (68 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 £214
includes taxes & fees
29 Sept - 30 Sept
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
A modern kitchen with stainless steel appliances, a dining area with a wooden bowl centerpiece, and a living room with a sofa and cushions.

8. Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds
Winter Haven
9.8 out of 10, Exceptional, (11 reviews)
"Great place. Perfect for my small group on a short visit. Shower is amazing. Had all amenities. Christopher was fantastic. "
United States
Judy A.
The price is £194
includes taxes & fees
5 Oct - 6 Oct
Modern Comfort, Pet Friendly, 2 King Beds
A compact living space with a dining area, kitchen, and a seating area with a sofa and a rug.

9. Family-Friendly 2BR Near LEGOLAND with Parking

Family-Friendly 2BR Near LEGOLAND with Parking
Winter Haven
8.6 out of 10, Excellent, (21 reviews)
"Absolutely great location for Legoland. The house had everything my family of 5 needed. Nice and quiet neighborhood. We would stay again! "
United States
Carolyn S.
The price is £153
includes taxes & fees
29 Sept - 30 Sept
Family-Friendly 2BR Near LEGOLAND with Parking
A living room with a brick fireplace, a sofa, a coffee table, and a dining area in the background.

10. 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 £297
includes taxes & fees
29 Sept - 30 Sept
Spacious 4-bedroom house in pleasant Winter Haven with AC
A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

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

Hook, Line & Leisure: Lakefront Gem w/ Porch!
Florence Villa
9.6 out of 10, Exceptional, (29 reviews)
"Nice place to stay for a weekend, had plenty of beds and baths, was clean and close to Lake Silver."
United States
Kelley K.
The price is £314
includes taxes & fees
1 Oct - 2 Oct
Hook, Line & Leisure: Lakefront Gem w/ Porch!
A living room with a grey sectional sofa, a white round coffee table, a fluffy rug, and a decorative mirror on the wall.

12. 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 £175
includes taxes & fees
29 Sept - 30 Sept
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
A kitchen with a dishwasher, a dining area with a chandelier, and a living room with a couch and a painting.

13. Your Winter Haven Oasis Awaits 3-bedroom house near Legoland in Winter Haven

Your Winter Haven Oasis Awaits 3-bedroom house near Legoland in Winter Haven
Lucerne Park
The price is £151
includes taxes & fees
29 Sept - 30 Sept
Your Winter Haven Oasis Awaits 3-bedroom house near Legoland in Winter Haven
An outdoor hot tub area with a pool, surrounded by chairs and a table.

14. Legoland Splash Escape with pool and hot tub!

Legoland Splash Escape with pool and hot tub!
Winter Haven
10.0 out of 10, Exceptional, (73 reviews)
"We had a great time staying here. The house was well maintained. The kids enjoyed the pool."
United States
Amy
The price is £246
includes taxes & fees
6 Oct - 7 Oct
Legoland Splash Escape with pool and hot tub!
A bedroom with a large bed, a ceiling fan, a mirror, and a small bedside table with a lamp.

15. 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
9.6 out of 10, Exceptional, (8 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 £219
includes taxes & fees
12 Oct - 13 Oct
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
A patio with a round table and chairs, a blue umbrella, and a view of a lake with a dock and a gazebo.

16. Peaceful Lakeside Retreat

Peaceful Lakeside Retreat
Winter Haven
9.4 out of 10, Exceptional, (13 reviews)
"This property was very nice! It was very relaxing and provided me with a very nice host location for family that I was visiting in the area. The property manager was extremely professional and accommodating."
United States
Shelby R.
The price is £311
includes taxes & fees
2 Oct - 3 Oct
Peaceful Lakeside Retreat
A kitchen with white cabinets, a dining table with chairs, and a ceiling fan.

17. 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, (3 reviews)
"Nice place very convenient for us. Would stay again"
United States
John G.
The price is £221
includes taxes & fees
15 Oct - 16 Oct
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

18. 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 £7,675
includes taxes & fees
17 Oct - 18 Oct
Family Friendly Lake House W/ Pool Near Legoland

19. Peaceful Place

Peaceful Place
Winter Haven
10.0 out of 10, Exceptional, (26 reviews)
"Great property!"
United States
Glenn C.
The price is £278
includes taxes & fees
29 Sept - 30 Sept
Peaceful Place
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
"My favorite! Stay here about 5 times a year."
Ingrid 3-night trip
Posted less than an hour ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Haven

Winter Haven Holiday Homes information

Number of reviews
274
Accommodation
23350 Holiday Homes
Lowest Price
£146
Highest Price
£7,675