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

Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winter Haven vacation rentals

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 ￥9,339
￥39,442 total
includes taxes & fees
Sep 27 - Sep 28
BlockHaven near Legoland & Disney
A swimming pool with a fence, lounge chairs, and a palm tree.

2. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (197 reviews)
"Clean room and private area loved it"
United States
Heather
The price is ￥10,497
￥11,757 total
includes taxes & fees
Oct 9 - Oct 10
Lake Ida Beach Resort
A building with a red door, numbered 132C, and a small porch area with a metal stool and a green bucket with a wooden stick.

3. Tiny Paradise

Tiny Paradise
Winter Haven
9.6 out of 10, Exceptional, (15 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 ￥11,589
￥20,600 total
includes taxes & fees
Sep 29 - Sep 30
Tiny Paradise
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.

4. 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 ￥17,463
￥30,163 total
includes taxes & fees
Oct 3 - Oct 4
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.

5. 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 ￥17,463
￥43,847 total
includes taxes & fees
Sep 26 - Sep 27
New Haven 5 mi to Legoland & 0.5 mi to dwntwn
A dining area with a glass table and two yellow chairs, a ceiling fan, and a door with a window.

6. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"Very nice property. The cottage was very clean and well laid out. Recommend 10/10"
United States
Ron O.
The price is ￥13,573
￥27,268 total
includes taxes & fees
Oct 5 - Oct 6
Charming Lakeside Cottage
A compact living space with a loft bed, a TV mounted on the wall displaying streaming services, a small bathroom, and a wooden floor.

7. 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 ￥11,113
￥23,623 total
includes taxes & fees
Sep 27 - Sep 28
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A wooden house with a porch, steps, and a fenced area with plants.

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 ￥19,050
￥47,863 total
includes taxes & fees
Sep 26 - Sep 27
The Old Haven - An Enduring Piece of Nostalgia
A spacious living room with a sofa, a recliner, and a glass coffee table. There is a kitchen area in the background with a microwave and refrigerator.

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

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
9.2 out of 10, Wonderful, (7 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 ￥18,256
￥44,728 total
includes taxes & fees
Sep 30 - Oct 1
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
A modern living room with a grey sofa, a grey armchair, a flat-screen TV, a white entertainment unit, and a kitchen area visible through an open doorway.

10. View Private Suite near LEGOLAND & Hospital

View Private Suite near LEGOLAND & Hospital
Winter Haven
The price is ￥9,971
￥20,537 total
includes taxes & fees
Oct 13 - Oct 14
View Private Suite near LEGOLAND & Hospital
A bedroom with a large bed, a ceiling fan, a mirror, and a small bedside table with a lamp.

11. 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 ￥12,408
￥43,619 total
includes taxes & fees
Sep 28 - Sep 29
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

12. 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 ￥19,844
￥48,109 total
includes taxes & fees
Sep 26 - Sep 27
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

13. 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 ￥26,115
￥63,945 total
includes taxes & fees
Oct 8 - Oct 9
Hook, Line & Leisure: Lakefront Gem w/ Porch!
A modern kitchen with stainless steel appliances, a dining area with a wooden bowl centerpiece, and a living room with a sofa and cushions.

14. 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 ￥17,131
￥39,970 total
includes taxes & fees
Oct 1 - Oct 2
Modern Comfort, Pet Friendly, 2 King Beds
A living room with a brick fireplace, a sofa, a coffee table, and a dining area in the background.

15. 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 ￥18,796
￥60,420 total
includes taxes & fees
Sep 28 - Sep 29
Spacious 4-bedroom house in pleasant Winter Haven with AC
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a built-in oven.

16. Legoland & Lakes Pool Home w/ Private Suite

Legoland & Lakes Pool Home w/ Private Suite
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"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
Legoland & Lakes Pool Home w/ Private Suite
A living room with a grey sofa, a wooden coffee table, a patterned rug, a TV, and a wall mural of underwater scenes.

17. 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 ￥10,001
￥43,358 total
includes taxes & fees
Sep 27 - Sep 28
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
A living room with a grey sectional sofa, a white round coffee table, a fluffy rug, and a decorative mirror on the wall.

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 ￥21,366
￥36,908 total
includes taxes & fees
Sep 27 - Sep 28
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

19. 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 ￥18,992
￥44,062 total
includes taxes & fees
Sep 28 - Sep 29
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

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)
"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 ￥19,526
￥64,751 total
includes taxes & fees
Sep 27 - Sep 28
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.
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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

10/10 Excellent
"Todo muy limpio"
guillermo 3-night trip
Posted 2 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

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
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  • 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!

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Frequently asked questions

Can I find a vacation rental in Winter Haven?

Yes, there are vacation rentals in Winter Haven close to LEGOLAND® Florida, or you can choose a more secluded option if you'd like a relaxing place to 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's the top vacation rental that Winter Haven has to offer?

Formosa Valley Resort by UNE Homes: This vacation home rental outside 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 vacation rentals are there in Winter Haven?

Choose from 57 Expedia vacation rentals in Winter Haven for a memorable vacation.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Indigo's Family Fun Center, whereas Inman Park and The Circle B Bar Reserve 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 vacation rentals like in Winter Haven?

Vacation rentals are private properties you can book for a few days or a quick weekend in Winter Haven. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.