Winter Haven Vacation Rentals

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Our top choices for Winter Haven vacation rentals

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
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
Apr 19 - Apr 20
Total with taxes and fees
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (191 reviews)
"We have stayed here several times. "
United States
Martha
$75 nightly
The price is $84
Apr 20 - Apr 21
Total with taxes and fees
Lake Ida Beach Resort

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Great communication with host. "
United States
Reid
$243 nightly
The price is $272
Apr 27 - Apr 28
Total with taxes and fees
BlockHaven near Legoland & Disney

Resort Home w Pool Games BBQ - Near Disney

Resort Home w Pool Games BBQ - Near Disney
2.5 star property
Kissimmee
Resort Home w Pool Games BBQ - Near Disney

Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (206 reviews)
"Camp Mack is a wonderful place to stay!"
United States
Tommy
$116 nightly
The price is $130
May 3 - May 4
Total with taxes and fees
Camp Mack Lodge, Marina & RV Resort

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.2 out of 10, Wonderful, (267 reviews)
"We love staying at this resort, great area"
United States
Mary
$132 nightly
The price is $150
Apr 16 - Apr 17
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando

Harmony Ensuite Room Shared Home No Car

Harmony Ensuite Room Shared Home No Car
2.5 star property
Kissimmee
$174 nightly
The price is $198
Apr 23 - Apr 24
Total with taxes and fees
Harmony Ensuite Room Shared Home No Car

Spacious Kissimmee Villa - 3 Mi to Disney World!

Spacious Kissimmee Villa - 3 Mi to Disney World!
3.0 star property
Windsor Hills
$411 nightly
The price is $411
Apr 19 - Apr 20
Total with taxes and fees
Spacious Kissimmee Villa - 3 Mi to Disney World!

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,875 reviews)
"Nice place to stay and close to the parks. "
United States
Kena
$104 nightly
The price is $118
Apr 16 - Apr 17
Total with taxes and fees
Vacation Village Orlando, Celebration

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very Good, (3,105 reviews)
"Great location and amenities."
United States
Jennifer
$275 nightly
The price is $312
Apr 16 - Apr 17
Total with taxes and fees
Regal Oaks Resort Vacation Townhomes by IDILIQ

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
$349 nightly
The price is $388
Apr 19 - Apr 20
Total with taxes and fees
Serenity - Family & Pet Friendly, Amazing Location

Bright 3BR Resort Condo Near Disney + Pools

Bright 3BR Resort Condo Near Disney + Pools
3.0 star property
Davenport
$342 nightly
The price is $352
Apr 20 - Apr 21
Total with taxes and fees
Bright 3BR Resort Condo Near Disney + Pools

Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse

Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse
3.5 star property
Kissimmee
$493 nightly
The price is $560
Apr 17 - Apr 18
Total with taxes and fees
Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse

Super YES - Many Amenities Relax GYM Courts

Super YES - Many Amenities Relax GYM Courts
2.0 star property
Kissimmee
$288 nightly
The price is $327
Apr 21 - Apr 22
Total with taxes and fees
Super YES - Many Amenities Relax GYM Courts

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
Davenport
9.2 out of 10, Wonderful, (553 reviews)
"Quiet, comfortable beds "
United States
Nicole
$133 nightly
The price is $149
May 5 - May 6
Total with taxes and fees
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Elita Inn

Elita Inn
3.0 star property
Dundee
7.4 out of 10, Good, (29 reviews)
"Very nice accommadations..friendly staff"
United States
lance
$80 nightly
The price is $90
May 15 - May 16
Total with taxes and fees
Elita Inn

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,858 reviews)
"Loved it had everything we needed"
United States
Kimberlee
$97 nightly
The price is $110
Apr 22 - Apr 23
Total with taxes and fees
Barefoot Suites

5 Mi to Disney: Family-friendly Kissimmee Retreat!

5 Mi to Disney: Family-friendly Kissimmee Retreat!
3.5 star property
Kissimmee
$261 nightly
The price is $293
Apr 22 - Apr 23
Total with taxes and fees
5 Mi to Disney: Family-friendly Kissimmee Retreat!

Orlando Getaway With Pool View Balcony

Orlando Getaway With Pool View Balcony
4.0 star property
Celebration
Orlando Getaway With Pool View Balcony

Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes
4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (209 reviews)
"The Formosa house was very clean and spacious for my family of 9 . The rooms are spacious and each had their own bathroom except for the two theme rooms that had a shared bathroom but it was very convenient. Kitchen has everything you need. The host was very fast to response with any questions. Definitely will be staying here again. We loved our stay here "
United States
jacqueline
$532 nightly
The price is $592
Apr 16 - Apr 17
Total with taxes and fees
Formosa Valley Resort by UNE Homes
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

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 $110 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.

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 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 Indigo's Family Fun Center, whereas The Circle B Bar Reserve and Rotary Park are a couple of great spots to enjoy the outdoors. Winter Haven City Tennis Center and Theatre Winter Haven 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.