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

Winter Haven Vacation Rentals

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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Winter Haven vacation rentals

A swimming pool with a fence, lounge chairs, and a palm tree.

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
$69 nightly
The price is $77
Oct 3 - Oct 4
Total with taxes and fees
Lake Ida Beach Resort
A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

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
$235 nightly
The price is $263
Sep 8 - Sep 9
Total with taxes and fees
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.

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.
$172 nightly
The price is $190
Sep 10 - Sep 11
Total with taxes and fees
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
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.

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.
$113 nightly
The price is $124
Sep 9 - Sep 10
Total with taxes and fees
Tiny Paradise
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
$284 nightly
The price is $312
Sep 3 - Sep 4
Total with taxes and fees
The Old Haven - An Enduring Piece of Nostalgia
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.

6. View Private Suite near LEGOLAND & Hospital

View Private Suite near LEGOLAND & Hospital
Winter Haven
$118 nightly
The price is $130
Sep 4 - Sep 5
Total with taxes and fees
View Private Suite near LEGOLAND & Hospital
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

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.
$287 nightly
The price is $315
Sep 12 - Sep 13
Total with taxes and fees
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

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

New Haven 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
$251 nightly
The price is $275
Sep 4 - Sep 5
Total with taxes and fees
New Haven 5 mi to Legoland & 0.5 mi to dwntwn

9. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
$156 nightly
The price is $172
Sep 3 - Sep 4
Total with taxes and fees
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.

10. 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.
$135 nightly
The price is $149
Sep 3 - Sep 4
Total with taxes and fees
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A living room with two blue sofas, a patterned ottoman, a ceiling fan, and a large abstract painting.

11. 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.
$294 nightly
The price is $325
Sep 11 - Sep 12
Total with taxes and fees
Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown
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.

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.
$254 nightly
The price is $279
Sep 3 - Sep 4
Total with taxes and fees
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
A modern kitchen with stainless steel appliances, a dining area with a wooden bowl centerpiece, and a living room with a sofa and cushions.

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.
$208 nightly
The price is $230
Sep 3 - Sep 4
Total with taxes and fees
Modern Comfort, Pet Friendly, 2 King Beds
A living room with a grey sofa, a wooden coffee table, a patterned rug, a TV, and a wall mural of underwater scenes.

14. 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.
$258 nightly
The price is $285
Sep 7 - Sep 8
Total with taxes and fees
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.

15. 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.
$209 nightly
The price is $231
Sep 3 - Sep 4
Total with taxes and fees
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
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
$460 nightly
The price is $509
Sep 25 - Sep 26
Total with taxes and fees
Legoland & Lakes Pool Home w/ Private Suite
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a built-in oven.

17. Legoland & Lakes Pool Home w/ Private Suite

Legoland & Lakes Pool Home w/ Private Suite
3.0 star property
Winter Haven
$452 nightly
The price is $506
Sep 25 - Sep 26
Total with taxes and fees
Legoland & Lakes Pool Home w/ Private Suite
A wooden table and chairs on a deck with a view of a lake and dock area.

18. Serene, Cozy, Lakefront Home with boat dock and Large Screened in porch!

Serene, Cozy, Lakefront Home with boat dock and Large Screened in porch!
Winter Haven
9.6 out of 10, Exceptional, (7 reviews)
"Everything was just as it was listed great place to stay"
United States
Renee T.
$336 nightly
The price is $372
Sep 3 - Sep 4
Total with taxes and fees
Serene, Cozy, Lakefront Home with boat dock and Large Screened in porch!

19. Peaceful Place

Peaceful Place
Winter Haven
10.0 out of 10, Exceptional, (26 reviews)
"Great property!"
United States
Glenn C.
$312 nightly
The price is $344
Sep 3 - Sep 4
Total with taxes and fees
Peaceful Place
A living room with a brick fireplace, a sofa, a coffee table, and a dining area in the background.

20. 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
$360 nightly
The price is $399
Sep 8 - Sep 9
Total with taxes and fees
Spacious 4-bedroom house in pleasant Winter Haven with AC
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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Excelente"
Christian 2-night trip
Posted less than an hour ago
Hilton Vacation Club Mystic Dunes Orlando

Find out more about Winter Haven

Everything you need to know about Winter Haven vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Haven vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Haven vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Haven. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Haven in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Haven rentals

At Expedia, we put the best Winter Haven vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Haven vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 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 vacation rentals are there in Winter Haven?

Choose from 61 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 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 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.