Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

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

Vacation Home in Winter Haven

BlockHaven near Legoland & Disney
3.5 star property
10.0 out of 10, Exceptional, (1 review)
"House was great, perfect central location. Very quiet neighborhood nice farm outside peaceful back yard seating area. "
United States
Wade
$231 nightly
The price is $259
Feb 1 - Feb 2
Total with taxes and fees
BlockHaven near Legoland & Disney
TV

Cottage in Winter Haven

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
10.0 out of 10, Exceptional, (2 reviews)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
$257 nightly
The price is $282
Jan 26 - Jan 27
Total with taxes and fees
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
TV, fireplace

Vacation Home in Winter Haven

Spacious 4-bedroom house in pleasant Winter Haven with AC
10.0 out of 10, Exceptional, (2 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
$333 nightly
The price is $368
Jan 26 - Jan 27
Total with taxes and fees
Spacious 4-bedroom house in pleasant Winter Haven with AC
Interior

Vacation Home in Winter Haven

Cozy 1 bedroom home in Winter Haven perfect for your getaway.
10.0 out of 10, Exceptional, (1 review)
"Yes the dogs liked it and they enjoyed walking in the neighborhood."
United States
John W.
$148 nightly
The price is $163
Jan 29 - Jan 30
Total with taxes and fees
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Outdoor pool, pool umbrellas, sun loungers

Cottage in Winter Haven

Lake Ida Beach Resort
3.0 star property
7.2 out of 10, Good, (188 reviews)
"We have stayed here several times. "
United States
Martha
$79 nightly
The price is $88
Jan 24 - Jan 25
Total with taxes and fees
Lake Ida Beach Resort
Exterior detail

Apartment in Winter Haven

Tiny Paradise
9.4 out of 10, Exceptional, (8 reviews)
"I have stayed on property a few times, first experience with tiny Paradise very quaint and clean enjoyed my stay."
United States
SUSAN
$113 nightly
The price is $124
Jan 26 - Jan 27
Total with taxes and fees
Tiny Paradise
Interior

Apartment in Winter Haven

The Unique cozy studio
10.0 out of 10, Exceptional, (1 review)
"Cool little place, love the outdoor private patio.Very close to everything downtown"
United States
Cory M.
$170 nightly
The price is $183
Jan 25 - Jan 26
Total with taxes and fees
The Unique cozy studio
Outdoor dining

Apartment in Winter Haven

⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance
10.0 out of 10, Exceptional, (3 reviews)
"The place was clean and tidy, accessible to a lot of stores and attractions in the surrounding area, and the hosts were SO nice and easy to contact throughout our stay-even checking in on us to make sure everything was going good. Would totally stay again!"
United States
Kaitlyn F.
$124 nightly
The price is $136
Jan 25 - Jan 26
Total with taxes and fees
⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance
Smart TV, foosball

Vacation Home in Winter Haven

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
9.4 out of 10, Exceptional, (66 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
$249 nightly
The price is $276
Jan 27 - Jan 28
Total with taxes and fees
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
House (3 Bedrooms) | Interior

Cottage in Winter Haven

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
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
$394 nightly
The price is $438
Feb 3 - Feb 4
Total with taxes and fees
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Smart TV, fireplace, printers

Vacation Home in Winter Haven

Modern Comfort, Pet Friendly, 2 King Beds
10.0 out of 10, Exceptional, (3 reviews)
"Great welcoming and answered every question I had. Highly recommend this lovely cottage. "
United States
Kristofer G.
$237 nightly
The price is $262
Jan 25 - Jan 26
Total with taxes and fees
Modern Comfort, Pet Friendly, 2 King Beds
Paper towels

Vacation Home in Winter Haven

Private/Spacious 1BR Central Near LegoLand 2 Miles
9.6 out of 10, Exceptional, (8 reviews)
"Location was great. Internet was great. Bed was good. Cleaned and comfortable.."
United States
Maria
$156 nightly
The price is $172
Jan 27 - Jan 28
Total with taxes and fees
Private/Spacious 1BR Central Near LegoLand 2 Miles
Fridge, microwave, stovetop, coffee/tea maker

Apartment in Winter Haven

Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
$127 nightly
The price is $145
Jan 31 - Feb 1
Total with taxes and fees
Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
Fridge, microwave, oven, stovetop

Vacation Home in Winter Haven

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
10.0 out of 10, Exceptional, (1 review)
"Nice place very convenient for us. Would stay again"
United States
John G.
$264 nightly
The price is $290
Jan 25 - Jan 26
Total with taxes and fees
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Microwave

Apartment in Winter Haven

Cozy 1-Bedroom Retreat Near Downtown & Legoland
10.0 out of 10, Exceptional, (2 reviews)
$158 nightly
The price is $175
Feb 14 - Feb 15
Total with taxes and fees
Cozy 1-Bedroom Retreat Near Downtown & Legoland
TV

Vacation Home in Winter Haven

Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes
10.0 out of 10, Exceptional, (1 review)
"The host was very accommodating and responsive. The house is clean, roomy, cute, and comfortable. There is so much to see and do in Winter Haven - I’ll return and stay at Rick’s Retreat again!"
United States
Mary R.
$310 nightly
The price is $342
Jan 26 - Jan 27
Total with taxes and fees
Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes
Fridge, microwave, oven, stovetop

Vacation Home in Winter Haven

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
9.8 out of 10, Exceptional, (7 reviews)
"Great location, clean and great communication with hosts "
United States
Angie Y.
$281 nightly
The price is $309
Jan 25 - Jan 26
Total with taxes and fees
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Living area

Vacation Home in Winter Haven

BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
$270 nightly
The price is $298
Feb 1 - Feb 2
Total with taxes and fees
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
Interior

Villa in Winter Haven

Family Vacation Home · 8 Minutes from Legoland Florida
10.0 out of 10, Exceptional, (1 review)
"Beautiful clean home. Lots of amenities. However it here were glass decorations on table. We moved them out of reach of 2 and 4 year old. Otherwise BEAUTIFUL! Definitely would stay here again."
United States
Roberta W.
$341 nightly
The price is $377
Jan 30 - Jan 31
Total with taxes and fees
Family Vacation Home · 8 Minutes from Legoland Florida
4 bedrooms, free WiFi, bed sheets

Vacation Home in Winter Haven

Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
10.0 out of 10, Exceptional, (3 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.
$338 nightly
The price is $373
Feb 2 - Feb 3
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

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent
"The room was clean everyday, breakfast was great as well. The employees were really welcoming and helpful. Very kind when my sister and I checked in. "
Anthony 3-night trip
Posted 1 day ago
Holiday Inn Resort Kissimmee by the Parks 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 $96 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?

The Berkley, Orlando: This vacation home rental outside of Winter Haven offers a furnished patio, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave, and a coffee maker. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Winter Haven?

Choose from 70 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 Rotary 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.