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, (2779)
"Its always a nice place to stay "
$98 nightly
The price is $112
Aug 25 - Aug 26
Total includes 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, (1575)
"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, (5601)
"I had a great stay "
$155 nightly
The price is $172
Aug 24 - Aug 25
Total includes taxes and fees
Summer Bay Orlando by Exploria Resorts

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (138)
"Great place, would definitely stay there again "
$114 nightly
The price is $130
Sep 19 - Sep 20
Total includes taxes and fees
Barefoot'n Resort Kissimmee Orlando

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1377)
"The best hotel "
Reunion Resort & Golf Club

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1882)
"Very nice property for family vacation)"
$107 nightly
The price is $121
Aug 26 - Aug 27
Total includes taxes and fees
The Berkley, Orlando

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very Good, (2961)
"Excellent service and stay "
$278 nightly
The price is $316
Aug 24 - Aug 25
Total includes taxes and fees
Regal Oaks Resort Vacation Townhomes by IDILIQ

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1371)
"Love that there was a private as well as a community pool"
$224 nightly
The price is $255
Aug 24 - Aug 25
Total includes 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, (1144)
"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, (135)
"Always a great place to stay"
Grand Lake Resort

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (143)
"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, (167)
"My children and I enjoyed our stay. This place is close to everything. The property managers responds within minutes for any inquires. You can also reach someone by phone at any hour. The home was very clean with everything you need! I would definitely recommend!"
$434 nightly
The price is $482
Aug 24 - Aug 25
Total includes taxes and fees
Formosa Valley Resort by UNE Homes

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1762)
"Location. Everything. Excelente.perfect"
$89 nightly
The price is $101
Sep 16 - Sep 17
Total includes taxes and fees
Barefoot Suites

Champions Gate condos by UNE

4.0 star property
9.2 out of 10, Wonderful, (27)
"Beautiful grounds and great location "
$276 nightly
The price is $314
Aug 24 - Aug 25
Total includes taxes and fees
Champions Gate condos by UNE

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, (483)
"Very nice hotel...Very safe and clean "
$91 nightly
The price is $101
Aug 23 - Aug 24
Total includes taxes and fees
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Encore Resort

4.0 star property
6.4 out of 10, (117)
"Great place "
Encore Resort

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

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2257)
"We had a great family vacation "
Caribe Cove Resort
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

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.