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Top Holiday Rentals in Winter Haven

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2793)
"Lovely property will stay here everytime"
The price is £83
includes taxes & fees
15 Sept - 16 Sept
Vacation Village at Parkway

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1579)
"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, (5603)
"I had a great stay "
The price is £117
includes taxes & fees
27 Aug - 28 Aug
Summer Bay Orlando by Exploria Resorts

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1381)
"The best hotel "
The price is £211
includes taxes & fees
27 Aug - 28 Aug
Reunion Resort & Golf Club

Magical Dreams

3.0 star property
10.0 out of 10, Exceptional, (1)
"estaba algo caliente pero nos contactamos con los encargados y nos solucionaron el problema "
The price is £95
includes taxes & fees
24 Aug - 25 Aug
Magical Dreams

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1885)
"Beautiful, perfect for a family getaway"
The price is £89
includes taxes & fees
25 Aug - 26 Aug
The Berkley, Orlando

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2963)
"Excellent service and stay "
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 "
The price is £91
includes taxes & fees
4 Sept - 5 Sept
Barefoot'n Resort Kissimmee Orlando

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1372)
"Very nice resort "
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, (135)
"Always a great place to stay"
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, (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!"
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."
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, (483)
"Very nice hotel...Very safe and clean "
The price is £75
includes taxes & fees
5 Sept - 6 Sept
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

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 holiday rental in Winter Haven?

Yes, there are holiday rentals in Winter Haven close to LEGOLAND® Florida, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Winter Haven has to offer?

The Berkley, Orlando: This holiday home rental outside of Winter Haven offers a furnished patio, a terrace and a BBQ 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 holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Winter Haven?

Choose from 144 Expedia holiday rentals in Winter Haven for a memorable holiday.

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 holiday rentals like in Winter Haven?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Haven. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.