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Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
$66 nightly
The price is $73
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, (24 reviews)
"Host was attentive and excellent!!!"
United States
jason s.
$190 nightly
The price is $210
Oct 18 - Oct 19
Total with taxes and fees
The Russell Lake House
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

3. 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.
$290 nightly
The price is $318
Oct 18 - Oct 19
Total with taxes and fees
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.

4. Lakefront Vibes w/ Lanai! Bird-watching Paradise

Lakefront Vibes w/ Lanai! Bird-watching Paradise
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
$361 nightly
The price is $404
Oct 18 - Oct 19
Total with taxes and fees
Lakefront Vibes w/ Lanai! Bird-watching Paradise
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.

5. 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.
$256 nightly
The price is $281
Oct 17 - Oct 18
Total with taxes and fees
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
A wooden house with a porch, steps, and a fenced area with plants.

6. The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia
Winter Haven
9.8 out of 10, Exceptional, (16 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
Oct 18 - Oct 19
Total with taxes and fees
The Old Haven - An Enduring Piece of Nostalgia
Living area

7. 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.
$254 nightly
The price is $281
Oct 18 - Oct 19
Total with taxes and fees
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
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
9.4 out of 10, Exceptional, (16 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.
$118 nightly
The price is $130
Oct 25 - Oct 26
Total with taxes and fees
Tiny Paradise
A modern kitchen with a stainless steel refrigerator, white cabinetry, a double sink, and a painting of flowers on the wall.

9. 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)
$251 nightly
The price is $275
Oct 17 - Oct 18
Total with taxes and fees
New Haven 5 mi to Legoland & 0.5 mi to dwntwn
A wooden table and chairs on a deck with a view of a lake and dock area.

10. 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)
"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.
$361 nightly
The price is $399
Oct 19 - Oct 20
Total with taxes and fees
Serene, Cozy, Lakefront Home with boat dock and Large Screened in porch!
A covered deck with a view of the water, a seating area with cushions, and a chair.

11. Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17

Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17
Winter Haven
10.0 out of 10, Exceptional, (8 reviews)
"Great home with lots of room and things to do. Everything was easy and we love staying here!"
United States
Megan D.
$778 nightly
The price is $860
Oct 19 - Oct 20
Total with taxes and fees
Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17
A kitchen with white cabinets, a dining table with chairs, and a ceiling fan.

12. 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, (3 reviews)
"Nice place very convenient for us. Would stay again"
United States
John G.
$268 nightly
The price is $294
Oct 17 - Oct 18
Total with taxes and fees
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
A bedroom with a bed covered in a colorful quilt, a small nightstand with a lamp, a window with curtains, and a TV stand with a TV.

13. 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
$214 nightly
The price is $240
Nov 12 - Nov 13
Total with taxes and fees
BlockHaven near Legoland & Disney
A modern living room with a black sofa, wooden flooring, and a ceiling fan.

14. Large Family Home, Legoland, Pet Friendly, 7 Beds

Large Family Home, Legoland, Pet Friendly, 7 Beds
Winter Haven
10.0 out of 10, Exceptional, (26 reviews)
"Everything was very nice and comfortable. "
United States
Gary B.
$366 nightly
The price is $405
Oct 19 - Oct 20
Total with taxes and fees
Large Family Home, Legoland, Pet Friendly, 7 Beds
A compact living space with a loft bed, a TV mounted on the wall displaying streaming services, a small bathroom, and a wooden floor.

15. 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
Oct 18 - Oct 19
Total with taxes and fees
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A kitchen with white cabinets, a black countertop, a window with blinds, and a light fixture.

16. Cozy 1-Bedroom Retreat Near Downtown & Legoland

Cozy 1-Bedroom Retreat Near Downtown & Legoland
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
$158 nightly
The price is $175
Nov 1 - Nov 2
Total with taxes and fees
Cozy 1-Bedroom Retreat Near Downtown & Legoland
A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

17. Lakefront Vibes w/ Lanai! Bird-Watching Paradise

Lakefront Vibes w/ Lanai! Bird-Watching Paradise
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.
$368 nightly
The price is $407
Oct 18 - Oct 19
Total with taxes and fees
Lakefront Vibes w/ Lanai! Bird-Watching Paradise
A dark brown leather sectional sofa with multiple cushions, a carpeted floor, and two wall-mounted dog portraits.

18. 10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney

10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
2.0 star property
Winter Haven
$419 nightly
The price is $456
Oct 19 - Oct 20
Total with taxes and fees
10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
A dining area with a glass table and two yellow chairs, a ceiling fan, and a door with a window.

19. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"Truly great people. We had a wonderful time! Peaceful and relaxing!!"
United States
Jeremy Kyle W.
$160 nightly
The price is $177
Oct 18 - Oct 19
Total with taxes and fees
Charming Lakeside Cottage
Fully equipped kitchen with stainless steel appliances & huge kitchen island

20. Family Friendly Lake House W/ Pool Near Legoland

Family Friendly Lake House W/ Pool Near Legoland
Winter Haven
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful place! Perfect place to relax and close to all the Orlando attractions. "
United States
Brandon B.
$8,276 nightly
The price is $9,169
Oct 21 - Oct 22
Total with taxes and fees
Family Friendly Lake House W/ Pool Near Legoland
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 & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

8/10 Good
"Nice"
Fredrick 5-night trip
Posted 3 hours ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

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 $105 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.