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Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (197 reviews)
"Clean room and private area loved it"
United States
Heather
$66 nightly
The price is $73
Oct 13 - Oct 14
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, (8 reviews)
"Very nice house for a small family! Close to everything!"
United States
Yuliett
$234 nightly
The price is $262
Oct 5 - Oct 6
Total with taxes and fees
BlockHaven near Legoland & Disney
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
9.4 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 4 - Oct 5
Total with taxes and fees
Tiny Paradise
A compact living space with a loft bed, a TV mounted on the wall displaying streaming services, a small bathroom, and a wooden floor.

4. 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 4 - Oct 5
Total with taxes and fees
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
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.

5. View Private Suite near LEGOLAND & Hospital

View Private Suite near LEGOLAND & Hospital
Winter Haven
$118 nightly
The price is $130
Oct 4 - Oct 5
Total with taxes and fees
View Private Suite near LEGOLAND & Hospital
A modern kitchen with a stainless steel refrigerator, white cabinetry, a double sink, and a painting of flowers on the wall.

6. 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)
$252 nightly
The price is $276
Oct 4 - Oct 5
Total with taxes and fees
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.

7. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"Very nice property. The cottage was very clean and well laid out. Recommend 10/10"
United States
Ron O.
$156 nightly
The price is $172
Oct 5 - Oct 6
Total with taxes and fees
Charming Lakeside Cottage
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.

8. 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.
$257 nightly
The price is $282
Oct 4 - Oct 5
Total with taxes and fees
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

9. 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.
$292 nightly
The price is $320
Oct 4 - Oct 5
Total with taxes and fees
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
A living room with a grey sofa, a wooden coffee table, a patterned rug, a TV, and a wall mural of underwater scenes.

10. 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.
$262 nightly
The price is $289
Oct 4 - Oct 5
Total with taxes and fees
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
Living area

11. 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
$257 nightly
The price is $284
Oct 4 - Oct 5
Total with taxes and fees
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
A compact hotel room with a bed, a sofa, a desk, a kitchenette, and a TV.

12. Private King Suite with W/D near LEGOLAND & Winter Haven Hospital

Private King Suite with W/D near LEGOLAND & Winter Haven Hospital
Winter Haven
8.4 out of 10, Very good, (9 reviews)
"Minor issues with the toilet but it was taken care of immediately. Overall a pleasant stay."
Canada
Mike S.
$166 nightly
The price is $183
Oct 4 - Oct 5
Total with taxes and fees
Private King Suite with W/D near LEGOLAND & Winter Haven Hospital
A compact living space with a dining area, kitchen, and a seating area with a sofa and a rug.

13. 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.
$189 nightly
The price is $209
Oct 4 - Oct 5
Total with taxes and fees
Family-Friendly 2BR Near LEGOLAND with Parking
A wooden house with a porch, steps, and a fenced area with plants.

14. 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
$286 nightly
The price is $314
Oct 4 - Oct 5
Total with taxes and fees
The Old Haven - An Enduring Piece of Nostalgia
A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

15. 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.
$371 nightly
The price is $410
Oct 4 - Oct 5
Total with taxes and fees
Lakefront vibes w/ lanai bird watching paradise
A bedroom with a large bed, a ceiling fan, a mirror, and a small bedside table with a lamp.

16. 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.
$265 nightly
The price is $293
Oct 12 - Oct 13
Total with taxes and fees
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
A modern kitchen with stainless steel appliances, a dining area with a wooden bowl centerpiece, and a living room with a sofa and cushions.

17. 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.
$214 nightly
The price is $237
Oct 6 - Oct 7
Total with taxes and fees
Modern Comfort, Pet Friendly, 2 King Beds
A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

18. 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 4 - Oct 5
Total with taxes and fees
Lakefront Vibes w/ Lanai Bird Watching Paradise
A wooden table and chairs on a deck with a view of a lake and dock area.

19. 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.
$361 nightly
The price is $399
Oct 4 - Oct 5
Total with taxes and fees
Serene, Cozy, Lakefront Home with boat dock and Large Screened in 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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"We had a great state"
Bob 5-night trip
Posted 2 hours 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 $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.