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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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winter Haven vacation rentals

Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors

1. 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
$231 nightly
The price is $259
Sep 20 - Sep 21
Total with taxes and fees
BlockHaven near Legoland & Disney
Outdoor pool, pool umbrellas, sun loungers

2. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (196 reviews)
"Clean room and private area loved it"
United States
Heather
$79 nightly
The price is $88
Sep 20 - Sep 21
Total with taxes and fees
Lake Ida Beach Resort
Exterior detail

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.
$113 nightly
The price is $124
Sep 30 - Oct 1
Total with taxes and fees
Tiny Paradise
Interior

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.
$172 nightly
The price is $190
Oct 3 - Oct 4
Total with taxes and fees
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Coffee/tea maker, fridge, microwave, oven

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)
$249 nightly
The price is $273
Sep 19 - Sep 20
Total with taxes and fees
New Haven 5 mi to Legoland & 0.5 mi to dwntwn
Interior

6. 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 20 - Sep 21
Total with taxes and fees
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
Smart TV

7. View Private Suite near LEGOLAND & Hospital

View Private Suite near LEGOLAND & Hospital
Winter Haven
$118 nightly
The price is $130
Sep 20 - Sep 21
Total with taxes and fees
View Private Suite near LEGOLAND & Hospital
TV

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.
$254 nightly
The price is $279
Sep 19 - Sep 20
Total with taxes and fees
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Coffee/tea maker, fridge, microwave, oven

9. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
$156 nightly
The price is $172
Sep 19 - Sep 20
Total with taxes and fees
Charming Lakeside Cottage
Coffee/tea maker, fridge, microwave, oven

10. 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
Sep 19 - Sep 20
Total with taxes and fees
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Terrace/patio

11. 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
$270 nightly
The price is $298
Sep 20 - Sep 21
Total with taxes and fees
The Old Haven - An Enduring Piece of Nostalgia
4 bedrooms, WiFi (free), bed sheets

12. 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.
$257 nightly
The price is $284
Sep 21 - Sep 22
Total with taxes and fees
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
House (3 Bedrooms) | Interior

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
$361 nightly
The price is $404
Sep 20 - Sep 21
Total with taxes and fees
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Living area

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.
$254 nightly
The price is $281
Sep 20 - Sep 21
Total with taxes and fees
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
TV, fireplace

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
$360 nightly
The price is $398
Sep 21 - Sep 22
Total with taxes and fees
Spacious 4-bedroom house in pleasant Winter Haven with AC
TV

16. 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.
$306 nightly
The price is $338
Sep 20 - Sep 21
Total with taxes and fees
Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown
Smart TV, fireplace, printers

17. 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.
$214 nightly
The price is $237
Sep 20 - Sep 21
Total with taxes and fees
Modern Comfort, Pet Friendly, 2 King Beds
Smart TV, fireplace

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.
$205 nightly
The price is $227
Sep 20 - Sep 21
Total with taxes and fees
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Smart TV

19. 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.
$165 nightly
The price is $182
Sep 21 - Sep 22
Total with taxes and fees
Private King Suite with W/D near LEGOLAND & Winter Haven Hospital
Dining

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.
$350 nightly
The price is $389
Sep 20 - Sep 21
Total with taxes and fees
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

8/10 Good
"The resort is beautiful, clean, and very well maintained. The staff was very nice and welcoming, and our beds were super comfortable, which is always a toss-up at most hotels! Our only real complaint was the water pressure and the shower. We could not figure out how to get the shower temperature right—it was scalding hot, and we couldn’t get any cold water to come through. The sink had cold water, so we knew it wasn’t an issue with the water supply, but we just couldn’t get the shower to cooperate. We also tried calling the front desk for assistance, but unfortunately, no one answered. Overall, we really enjoyed our stay and thought the resort itself was beautiful. Hopefully, the shower issue and front desk availability are things they can improve, because otherwise it was a great experience!"
Melissa 1-night trip
Posted 1 hour ago
Kompose Boutique Resort at Theme Parks

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 59 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.