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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winter Haven vacation homes

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

1. 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 ￥9,946
￥40,239 total
includes taxes & fees
Aug 17 - Aug 18
BlockHaven near Legoland & Disney
Interior

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 ￥17,520
￥30,102 total
includes taxes & fees
Sep 11 - Sep 12
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Terrace/patio

3. 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 ￥19,112
￥49,931 total
includes taxes & fees
Aug 14 - Aug 15
The Old Haven - An Enduring Piece of Nostalgia
Coffee/tea maker, fridge, microwave, oven

4. 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 ￥19,909
￥50,975 total
includes taxes & fees
Aug 29 - Aug 30
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
4 bedrooms, WiFi (free), bed sheets

5. 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 ￥16,067
￥47,770 total
includes taxes & fees
Aug 16 - Aug 17
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
Coffee/tea maker, fridge, microwave, oven

6. 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 ￥19,924
￥45,267 total
includes taxes & fees
Aug 17 - Aug 18
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
TV, fireplace

7. 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 ￥14,653
￥58,459 total
includes taxes & fees
Sep 11 - Sep 12
Spacious 4-bedroom house in pleasant Winter Haven with AC
Living area

8. 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 ￥10,328
￥45,289 total
includes taxes & fees
Aug 20 - Aug 21
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
Outdoor dining

9. Legoland Splash Escape with pool and hot tub!

Legoland Splash Escape with pool and hot tub!
Winter Haven
10.0 out of 10, Exceptional, (66 reviews)
"We had a wonderful stay. Property was as listed and pool and activities were great for our family. "
United States
Christy H.
The price is ￥20,083
￥52,171 total
includes taxes & fees
Aug 24 - Aug 25
Legoland Splash Escape with pool and hot tub!
TV

10. Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown

Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown
Winter Haven
10.0 out of 10, Exceptional, (12 reviews)
"The house was really great. It was also very clean, updated, comfortable and very close to great restaurants. Highly recommend this house."
United States
Felix P.
The price is ￥19,924
￥50,367 total
includes taxes & fees
Aug 19 - Aug 20
Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown
Smart TV, fireplace, printers

11. Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds
Winter Haven
10.0 out of 10, Exceptional, (9 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 ￥20,848
￥44,696 total
includes taxes & fees
Aug 27 - Aug 28
Modern Comfort, Pet Friendly, 2 King Beds
Smart TV, fireplace

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 ￥21,518
￥36,533 total
includes taxes & fees
Aug 20 - Aug 21
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Interior

13. Peaceful Lakeside Retreat

Peaceful Lakeside Retreat
Winter Haven
9.2 out of 10, Wonderful, (12 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 ￥25,885
￥68,689 total
includes taxes & fees
Aug 26 - Aug 27
Peaceful Lakeside Retreat
Dining

14. 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 ￥21,979
￥67,957 total
includes taxes & fees
Sep 11 - Sep 12
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Coffee/tea maker, fridge, microwave, oven

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

Historic Manor, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Winter Haven
9.8 out of 10, Exceptional, (33 reviews)
"Perfect place to stay!"
United States
Rich S.
The price is ￥31,559
￥76,086 total
includes taxes & fees
Aug 25 - Aug 26
Historic Manor, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Interior

16. Cozy 2-bedroom house in a beautiful Winter Haven area near Legoland and BokTower

Cozy 2-bedroom house in a beautiful Winter Haven area near Legoland and BokTower
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"The host was amazing. Felt very welcomed! Great house to stay "
United States
Michelle M.
The price is ￥22,218
￥42,151 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 2-bedroom house in a beautiful Winter Haven area near Legoland and BokTower
Dining

17. Lakefront Heated Pool Home w/ Hot Tub, Dock & Sunset Views Near LEGOLAND

Lakefront Heated Pool Home w/ Hot Tub, Dock & Sunset Views Near LEGOLAND
Winter Haven
The price is ￥33,711
￥80,455 total
includes taxes & fees
Sep 7 - Sep 8
Lakefront Heated Pool Home w/ Hot Tub, Dock & Sunset Views Near LEGOLAND
Coffee/tea maker, fridge, microwave, oven

18. Peaceful Place

Peaceful Place
Winter Haven
10.0 out of 10, Exceptional, (26 reviews)
"Great property!"
United States
Glenn C.
The price is ￥24,705
￥58,464 total
includes taxes & fees
Aug 31 - Sep 1
Peaceful Place
Interior

19. 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 ￥25,104
￥31,306 total
includes taxes & fees
Aug 26 - Aug 27
Your Winter Haven Oasis Awaits 3-bedroom house near Legoland in Winter Haven
4 bedrooms, iron/ironing board, WiFi, bed sheets

20. White Door House!

White Door House!
Winter Haven
The price is ￥24,909
￥70,754 total
includes taxes & fees
Sep 12 - Sep 13
White Door House!
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.
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Top Winter Haven Hotel Reviews

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8/10 Good
"Stayed for four days and really loved how close the hotel was to everything. There was so much available at the resort that you honestly didn’t need to leave. The biggest downside was the timeshare pressure. The way they try to push you into attending a timeshare tour felt very pushy and honestly a little slimy. I’m on vacation to relax, not to be hounded about sitting through a sales presentation for hours. The resort itself was nice, but the timeshare antics really took away from the experience. Because of that, I probably wouldn’t stay again."
Michael 4-night trip
Posted less than an hour ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Find out more about Winter Haven

Winter Haven Vacation Homes information

Number of reviews
292
Accommodation
22305 Vacation Homes
Lowest Price
￥30,102
Highest Price
￥80,455