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

Winter Haven Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (198 reviews)
"Clean room and private area loved it"
United States
Heather
$70 nightly
The price is $79
Nov 15 - Nov 16
Total with taxes and fees
Lake Ida Beach Resort
A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

2. The Russell Lake House

The Russell Lake House
Winter Haven
9.8 out of 10, Exceptional, (25 reviews)
"Nice place!"
United States
Jake D.
$181 nightly
The price is $201
Nov 6 - Nov 7
Total with taxes and fees
The Russell Lake House
A kitchen with white cabinets, a dining table with chairs, and a ceiling fan.

3. 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, (4 reviews)
"Nice place very convenient for us. Would stay again"
United States
John G.
$244 nightly
The price is $270
Nov 9 - Nov 10
Total with taxes and fees
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

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, (14 reviews)
"Nice house for our stay."
United States
Debi K.
$276 nightly
The price is $304
Nov 7 - Nov 8
Total with taxes and fees
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

5. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (8 reviews)
"Very nice house for a small family! Close to everything!"
United States
Yuliett
$211 nightly
The price is $237
Nov 12 - Nov 13
Total with taxes and fees
BlockHaven near Legoland & Disney
Living area

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)
"Nice place and convenient"
United States
Tim M.
$242 nightly
The price is $269
Nov 8 - Nov 9
Total with taxes and fees
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
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.

7. 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.
$242 nightly
The price is $267
Nov 6 - Nov 7
Total with taxes and fees
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
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.

8. Tiny Paradise

Tiny Paradise
Winter Haven
9.6 out of 10, Exceptional, (17 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.
$102 nightly
The price is $114
Nov 11 - Nov 12
Total with taxes and fees
Tiny Paradise
A wooden house with a porch, steps, and a fenced area with plants.

9. The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia
Winter Haven
9.8 out of 10, Exceptional, (17 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
$272 nightly
The price is $300
Nov 9 - Nov 10
Total with taxes and fees
The Old Haven - An Enduring Piece of Nostalgia
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.
$127 nightly
The price is $141
Nov 8 - Nov 9
Total with taxes and fees
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A modern kitchen with a stainless steel refrigerator, white cabinetry, a double sink, and a painting of flowers on the wall.

11. 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)
$237 nightly
The price is $261
Nov 8 - Nov 9
Total with taxes and fees
New Haven 5 mi to Legoland & 0.5 mi to dwntwn
A kitchen with white cabinets, a black countertop, a window with blinds, and a light fixture.

12. Cozy 1-Bedroom Retreat Near Downtown & Legoland

Cozy 1-Bedroom Retreat Near Downtown & Legoland
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
$137 nightly
The price is $152
Nov 7 - Nov 8
Total with taxes and fees
Cozy 1-Bedroom Retreat Near Downtown & Legoland
An outdoor hot tub area with a pool, surrounded by chairs and a table.

13. Legoland Splash Escape with pool and hot tub!

Legoland Splash Escape with pool and hot tub!
Winter Haven
9.8 out of 10, Exceptional, (78 reviews)
"Great location"
United States
Michelle
$282 nightly
The price is $313
Nov 8 - Nov 9
Total with taxes and fees
Legoland Splash Escape with pool and hot tub!
Private kitchen

14. Peaceful Place

Peaceful Place
Winter Haven
10.0 out of 10, Exceptional, (28 reviews)
"Great property!"
United States
Glenn C.
$348 nightly
The price is $388
Nov 9 - Nov 10
Total with taxes and fees
Peaceful Place
A wooden table and chairs on a deck with a view of a lake and dock area.

15. 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, (8 reviews)
"Beautiful property extra clean and host was great. We saved it as one of our favorite places for a quick weekend getaway. We will be back for sure!"
United States
Brian M.
$346 nightly
The price is $384
Nov 23 - Nov 24
Total with taxes and fees
Serene, Cozy, Lakefront Home with boat dock and Large Screened in porch!
A kitchen with a dining table, chairs, and a ceiling fan.

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

Cozy 3br 2ba Winter Haven Getaway Chain of Lakes
Winter Haven
10.0 out of 10, Exceptional, (15 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.
$299 nightly
The price is $299
Nov 16 - Nov 17
Total with taxes and fees
Cozy 3br 2ba Winter Haven Getaway Chain of Lakes
A compact living space with a dining area, kitchen, and a seating area with a sofa and a rug.

17. 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.
$178 nightly
The price is $198
Nov 8 - Nov 9
Total with taxes and fees
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.

18. 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
$359 nightly
The price is $399
Nov 16 - Nov 17
Total with taxes and fees
Spacious 4-bedroom house in pleasant Winter Haven with AC
A living room with a grey sectional sofa, a white round coffee table, a fluffy rug, and a decorative mirror on the wall.

19. 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.
$200 nightly
The price is $222
Nov 8 - Nov 9
Total with taxes and fees
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
A bedroom with a large bed, a ceiling fan, a mirror, and a small bedside table with a lamp.

20. 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.
$262 nightly
The price is $291
Nov 16 - Nov 17
Total with taxes and fees
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
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

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent
"The staff was very nice and attentive. The room was clean and comfortable. Everything is walking distance. Great location."
Layla 1-night trip
Posted less than an hour ago
Margaritaville Resort Orlando with H2O Waterpark

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 $102 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 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 53 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 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 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.