Winter Haven Holiday Rentals

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Check prices for these dates

Tonight
31 Mar - 1 Apr
Tomorrow
1 Apr - 2 Apr
This weekend
4 Apr - 6 Apr
Next weekend
11 Apr - 13 Apr

Holiday Rentals in Winter Haven

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1839)
"Very clean and the staff was really nice "
The price is HK$721
HK$950 total
includes taxes & fees
13 Apr - 14 Apr
Vacation Village at Parkway
Summer Bay Orlando by Exploria Resorts
5 outdoor pools

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5278)
"Nice place"
The price is HK$910
HK$1,269 total
includes taxes & fees
7 Apr - 8 Apr
Summer Bay Orlando by Exploria Resorts
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1290)
"We absolutely loved our stay. The villa was spacious and modern. The resort is huge and has nice amenities. We especially loved the shuttle service, which we used daily to get to the water park, sunset walk restaurants, and main pool area. Our only disappointment was our villa being so close to a very high traffic, noisy road. It was too noisy to relax and sit outside. If we return, we will request a villa in a different area."
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.4 out of 10, Exceptional, (38)
"We really loved the place but the bathroom wasn’t clean and smelled of urine. The blankets on the bed were only two sheets and a very thin blanket. Overall, we liked it though"
The price is HK$755
HK$954 total
includes taxes & fees
1 Apr - 2 Apr
Barefoot'n Resort Kissimmee Orlando
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1240)
"BEAUTIFUL RESORT PLENTY THINGS TO DO! STAFF VERY FRIENDLY AND HELP. WE ENJOYED OUR STAY!"
The price is HK$1,628
HK$2,217 total
includes taxes & fees
21 Apr - 22 Apr
Reunion Resort & Golf Club
Regal Oaks Resort Vacation Townhomes by IDILIQ
2 outdoor pools, open 8:00 AM to 9:00 PM, pool cabanas (surcharge)

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2858)
"Definitely one of the most convenient resorts. So close to everything and private. Easy to unwind after a long day here"
The price is HK$940
HK$2,603 total
includes taxes & fees
3 Apr - 4 Apr
Regal Oaks Resort Vacation Townhomes by IDILIQ
The Berkley, Orlando
Lobby sitting area

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1716)
"Lovely property."
The price is HK$1,052
HK$1,271 total
includes taxes & fees
1 Apr - 2 Apr
The Berkley, Orlando
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
2 outdoor pools, open 8 AM to 10 PM, pool loungers

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

3.5 star property
9.2 out of 10, Wonderful, (432)
"Propery is clean and well maintained. The rooms are spacious. There is a nice pool and Activities Center. I think the only negative about this property is no restaurant or pool bar. Even without those, its an awesome choice."
The price is HK$926
HK$1,155 total
includes taxes & fees
1 Apr - 2 Apr
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Magic Village Yards, Trademark Collection by Wyndham
Outdoor pool, pool umbrellas, pool loungers

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1126)
"Great stay "
Magic Village Yards, Trademark Collection by Wyndham
Barefoot Suites
Aerial view

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1711)
"Excellent location and cost benefit, I will really be back."
The price is HK$745
HK$947 total
includes taxes & fees
1 Apr - 2 Apr
Barefoot Suites
Luxury 20 bedroom Reunion Villas @ Disney's Doorstep
Terrace/patio

Luxury 20 bedroom Reunion Villas @ Disney's Doorstep

9.2 out of 10, Wonderful, (89)
"One pool did not work correctly so wasn't used. Paid alot of money and think that should have been included with price of house. Asked for my money back"
Luxury 20 bedroom Reunion Villas @ Disney's Doorstep
Encantada Resort Vacation Townhomes by IDILIQ
2 outdoor pools, pool umbrellas, pool loungers

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1330)
"I recently stayed at Encantada Resort Vacation Townhomes by IDILIQ in Four Corners, Florida, from December 23 to January 2, and it was absolutely fantastic! The resort provided the perfect balance of relaxation and convenience. The townhome was spacious, clean, and well-maintained, with all the amenities we needed to feel at home. The fully equipped kitchen made it easy to prepare meals, and the private patio with a hot tub was an incredible touch for unwinding after a day of exploring. The...
The price is HK$819
HK$2,054 total
includes taxes & fees
8 Apr - 9 Apr
Encantada Resort Vacation Townhomes by IDILIQ
Villas At Regal Palms
Outdoor pool, pool loungers

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very good, (532)
"The villa we stayed in could use some updating"
Villas At Regal Palms
Blissful Bay
Full-sized fridge, microwave, oven, stovetop

Blissful Bay

3.0 star property
7.6 out of 10, Good, (16)
"All of house is great. Meet new people vacationing from other places really great stay."
Blissful Bay
Bahama Bay Resort
Property grounds

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2069)
"We enjoyed our stay, even tho people kept making judgements(not thr employees). Also, i am disappointed with housekeeping because my black and white soft blanket was left there. When i called they said hey did not receive anything from housekeeping. They would check and get back to me. Which they did. Unfortunately still i do not have my blanket and i know it was left there. "
Bahama Bay Resort
Encore Resort
Outdoor pool

Encore Resort

4.0 star property
6.4 out of 10, (114)
"It was a very nice home. My family had a great time"
Encore Resort
Caribe Cove Resort
Outdoor pool, a heated pool

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2246)
"Had problems with the door opener "
Caribe Cove Resort
Champions Gate condos by UNE
2 outdoor pools

Champions Gate condos by UNE

4.0 star property
9.2 out of 10, Wonderful, (9)
"Gorgeous "
The price is HK$1,053
HK$2,607 total
includes taxes & fees
1 Apr - 2 Apr
Champions Gate condos by UNE
Formosa Valley Resort by UNE Homes
Private pool

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (144)
"Very beautiful home, lots of space"
Formosa Valley Resort by UNE Homes
Leisure Lounge
Outdoor pool

Leisure Lounge

3.0 star property
8.0 out of 10, Very good, (12)
"i liked having the amenities of home. comfortable bed. patio/pool area is nice. other guests were nice. good community to go for walks. some noise from other guests like any occupied house. would rent this again for a similar situation."
Leisure Lounge
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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Other types of properties in Winter Haven you may be interested in

Best Western Plus Winter Haven Inn & Suites 
Desk, laptop workspace, blackout curtains, iron/ironing board

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
9.4 out of 10, Exceptional, (747)
"Breakfast fantástic!!! Good service"
The price is HK$1,156
HK$1,294 total
includes taxes & fees
1 May - 2 May
Best Western Plus Winter Haven Inn & Suites 
Howard Johnson by Wyndham Winter Haven FL
Blackout curtains, iron/ironing board, free cots/infant beds

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
7.0 out of 10, Good, (1208)
"Awesome "
The price is HK$793
HK$889 total
includes taxes & fees
6 Apr - 7 Apr
Howard Johnson by Wyndham Winter Haven FL
Home2 Suites By Hilton Winter Haven
Terrace/patio

Home2 Suites By Hilton Winter Haven

3.0 star property
8.8 out of 10, Excellent, (51)
"Exactly what I needed "
The price is HK$1,051
HK$1,177 total
includes taxes & fees
20 Apr - 21 Apr
Home2 Suites By Hilton Winter Haven
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.

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 134 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.