Winter Haven Vacation Rentals

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Vacation Rentals in Winter Haven

Our top choices for Winter Haven vacation rentals

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2813)
"Lovely property will stay here everytime"
$94 nightly
The price is $107
Sep 28 - Sep 29
Total with taxes and fees
Vacation Village at Parkway

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1590)
"Great place"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5605)
"I had a great stay "
$155 nightly
The price is $172
Aug 31 - Sep 1
Total with taxes and fees
Summer Bay Orlando by Exploria Resorts

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1383)
"The best hotel "
Reunion Resort & Golf Club

Magical Dreams

4.0 star property
10.0 out of 10, Exceptional, (1)
"estaba algo caliente pero nos contactamos con los encargados y nos solucionaron el problema "
$121 nightly
The price is $138
Aug 30 - Aug 31
Total with taxes and fees
Magical Dreams

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1892)
"Beautiful, perfect for a family getaway"
$117 nightly
The price is $132
Sep 1 - Sep 2
Total with taxes and fees
The Berkley, Orlando

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very Good, (2969)
"Excellent service and stay "
$281 nightly
The price is $319
Sep 1 - Sep 2
Total with taxes and fees
Regal Oaks Resort Vacation Townhomes by IDILIQ

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (138)
"Great place, would definitely stay there again "
$110 nightly
The price is $125
Sep 27 - Sep 28
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1374)
"Very nice resort "
$219 nightly
The price is $249
Sep 1 - Sep 2
Total with taxes and fees
Encantada Resort Vacation Townhomes by IDILIQ

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1145)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (136)
"It’s a great place "
Grand Lake Resort

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (144)
"Fairly quiet, beautiful view. We would 100% stay here again."
Lifetime of Vacations Resort

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (170)
"Great stay"
$480 nightly
The price is $534
Aug 31 - Sep 1
Total with taxes and fees
Formosa Valley Resort by UNE Homes

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1764)
"We have stayed numerous times. We love the property and love staying across the street from Fun Spot. Its nice to be able to stroll out every evening, shop, dine and have some fun. The 2 bedroom was very nice, clean and super roomy! We will be back as usual."
$103 nightly
The price is $117
Sep 9 - Sep 10
Total with taxes and fees
Barefoot Suites

Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool

9.6 out of 10, Exceptional, (48)
"Great location Sun all day and communication with management company was fantastic Will definitely stay again I’ve stayed for over 30 yrs and the best villa yet"
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool

Summerville Vacation Homes by Columbia Management

4.0 star property
8.4 out of 10, Very Good, (151)
"Not enough parking "
Summerville Vacation Homes by Columbia Management

Royal Laguna Villas By Magical Memories

3.5 star property
7.0 out of 10, Good, (2336)
"the apartment is comfortable and pleasant but the air conditioning does not work, there is only a ceiling fan in the main room and in the living room. They did not give us the card for the pool area and it was a problem to pay and get the lockbox code."
Royal Laguna Villas By Magical Memories

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

3.5 star property
9.2 out of 10, Wonderful, (484)
"Very nice hotel...Very safe and clean "
$113 nightly
The price is $126
Sep 5 - Sep 6
Total with taxes and fees
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Luxury 20 bedroom Reunion Villas @ Disney's Doorstep

9.2 out of 10, Wonderful, (96)
"Excellent facilities close to many places to golf and have fun"
Luxury 20 bedroom Reunion Villas @ Disney's Doorstep

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very Good, (577)
"This was the 2nd time we’ve stayed at Regal Palms and will definitely be back again. "
Villas At Regal Palms
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

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 $107 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 144 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.