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

Winter Haven Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winter Haven holiday rentals

Outdoor pool

1. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (194 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is HK$557
HK$624 total
includes taxes & fees
9 Sept - 10 Sept
Lake Ida Beach Resort
Living area

2. 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 HK$546
HK$2,042 total
includes taxes & fees
1 Sept - 2 Sept
BlockHaven near Legoland & Disney
Interior

3. 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 HK$862
HK$1,474 total
includes taxes & fees
31 Aug - 1 Sept
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Exterior detail

4. Tiny Paradise

Tiny Paradise
Winter Haven
9.6 out of 10, Exceptional, (14 reviews)
"Check in was easy, this little house had everything we needed! Owner very responsive to needs very quickly through app. We would stay again!"
United States
Cheryl K.
The price is HK$572
HK$1,017 total
includes taxes & fees
9 Sept - 10 Sept
Tiny Paradise
Interior

5. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, Wonderful, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
The price is HK$549
HK$1,167 total
includes taxes & fees
30 Aug - 31 Aug
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
Living area

6. View Private Suite near LEGOLAND & Hospital

View Private Suite near LEGOLAND & Hospital
Winter Haven
The price is HK$494
HK$1,017 total
includes taxes & fees
4 Sept - 5 Sept
View Private Suite near LEGOLAND & Hospital
Private kitchen

7. 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 HK$980
HK$2,470 total
includes taxes & fees
25 Sept - 26 Sept
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Terrace/patio

8. 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 HK$941
HK$2,387 total
includes taxes & fees
26 Sept - 27 Sept
The Old Haven - An Enduring Piece of Nostalgia
Living area

9. 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 HK$494
HK$2,243 total
includes taxes & fees
30 Aug - 31 Aug
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
Exterior

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

New Haven 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
The price is HK$862
HK$2,165 total
includes taxes & fees
30 Aug - 31 Aug
New Haven 5 mi to Legoland & 0.5 mi to dwntwn
Dining

11. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
The price is HK$670
HK$1,346 total
includes taxes & fees
26 Sept - 27 Sept
Charming Lakeside Cottage
Living area

12. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
9.0 out of 10, Wonderful, (6 reviews)
"Wonderful little cottage filled with fun for the whole family. Cozy backyard to enjoy some sunshine and read a book. Close to downtown shops and restaurants. Owners were quick to respond to questions. Would happily stay here again."
United States
Rachel B.
The price is HK$901
HK$2,209 total
includes taxes & fees
4 Sept - 5 Sept
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Living area

13. Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds
Winter Haven
10.0 out of 10, Exceptional, (10 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 HK$769
HK$1,872 total
includes taxes & fees
1 Sept - 2 Sept
Modern Comfort, Pet Friendly, 2 King Beds
Private kitchen

14. 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 HK$980
HK$2,226 total
includes taxes & fees
22 Sept - 23 Sept
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
Interior

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

Hook, Line & Leisure: Lakefront Gem w/ Porch!
3.0 star property
Florence Villa
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
United States
John
The price is HK$1,293
HK$3,167 total
includes taxes & fees
31 Aug - 1 Sept
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Living area

16. 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, (14 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 HK$1,019
HK$2,529 total
includes taxes & fees
30 Aug - 31 Aug
Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown
Outdoor dining

17. Legoland Splash Escape with pool and hot tub!

Legoland Splash Escape with pool and hot tub!
Winter Haven
10.0 out of 10, Exceptional, (69 reviews)
"We had a great time staying here. The house was well maintained. The kids enjoyed the pool."
United States
Amy
The price is HK$988
HK$2,589 total
includes taxes & fees
31 Aug - 1 Sept
Legoland Splash Escape with pool and hot tub!
Living area

18. 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 HK$1,058
HK$1,828 total
includes taxes & fees
30 Aug - 31 Aug
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Living area

19. 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 HK$878
HK$3,053 total
includes taxes & fees
20 Sept - 21 Sept
Spacious 4-bedroom house in pleasant Winter Haven with AC
Dining

20. 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 HK$1,082
HK$3,321 total
includes taxes & fees
25 Sept - 26 Sept
Hook, Line & Leisure: Lakefront Gem w/ Porch!
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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Awesome place to stay very quiet neighborhood"
Kristienrei 3-night trip
Posted 5 hours ago
Hilton Vacation Club Mystic Dunes Orlando

Find out more about Winter Haven

Search for holiday rentals in Winter Haven on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Haven using one of the methods below:

  • View our selection of featured holiday rentals in Winter Haven
  • Use the map to find apartments and other holiday homes in the Winter Haven neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Haven while they last

Look no further and take a look at our great range of rental properties in Winter Haven!

Frequently asked questions

Can I find a holiday rental in Winter Haven?

Yes, there are holiday rentals in Winter Haven close to LEGOLAND® Florida, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Winter Haven speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave time to check out the gardens and entertainment venues during your visit.

What are some of the best holiday rentals that Winter Haven has to offer?

Formosa Valley Resort by UNE Homes: This holiday home rental outside of Winter Haven is equipped with an outdoor pool, air conditioning and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

How many holiday rentals are there in Winter Haven?

Choose from 60 Expedia holiday rentals in Winter Haven for a memorable holiday.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Peppa Pig Theme Park Florida, whereas The Circle B Bar Reserve and Inman Park are a couple of great spots to enjoy the outdoors. Theatre Winter Haven and Chain of Lakes Park are other places to visit while you're in town.

What are holiday rentals like in Winter Haven?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Haven. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.