Winter Haven Holiday Rentals

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Holiday Rentals in Winter Haven

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1196)
"Stayed at cottages. Good size homes. A bit of a drive back to the main hotel with the pools and bars. But there is a shuttle service that will take you over there and back. There were plenty of smaller side pools that were within walking distance from our cottage. We didn’t have enough towels and bedsheets and/or pillows, but they were brought over to our cottage by housekeeping. There is only housekeeping services available for an extra fee. The stay was nice and we would go back there again."
Margaritaville Resort Orlando Cottages by Rentyl

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5137)
"It was a great experience. Will come back again "
The price is AU$266
includes taxes & fees
3 Mar - 4 Mar
Summer Bay Orlando by Exploria Resorts

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1470)
"I absolutely LOVED this place!! It was like a serene getaway!!! My family will Be visiting again!! "
The price is AU$196
includes taxes & fees
3 Mar - 4 Mar
Vacation Village at Parkway

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1671)
"The best staff at any resort we have ever stayed at. It was clean, very well taken care of. The pool and hot tub area was always in pristine cleanliness. My only complaint is the furniture, it’s not a comfortable couch and the living room chairs weren’t any better. "
The price is AU$394
includes taxes & fees
27 Feb - 28 Feb
The Berkley, Orlando

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1218)
"Excellent stay "
The price is AU$454
includes taxes & fees
3 Mar - 4 Mar
Reunion Resort & Golf Club

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1687)
"Would recommend "
The price is AU$164
includes taxes & fees
19 Feb - 20 Feb
Barefoot Suites

Holiday Inn Club Vacations Orlando Breeze Resort

3.5 star property
9.2 out of 10, Wonderful, (410)
"The front desk the people was very nice they were very courtesy and friendly especially Miss Sasha she was a very nice person keep up the good."
The price is AU$288
includes taxes & fees
17 Feb - 18 Feb
Holiday Inn Club Vacations Orlando Breeze Resort

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2835)
"Fantastic resort shame that the hot water wasn’t working properly and it took reporting it 3 times to get it sorted "
The price is AU$570
includes taxes & fees
10 Mar - 11 Mar
Regal Oaks Resort Vacation Townhomes by IDILIQ

Champions Gate condos by UNE

4.0 star property
8.0 out of 10, Very good, (4)
"Very nice condo at a very good price yes especially for a family or for a larger group."
The price is AU$628
includes taxes & fees
13 Mar - 14 Mar
Champions Gate condos by UNE

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1118)
"Location was good. "
Magic Village Yards, Trademark Collection by Wyndham

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very good, (524)
"It advatized wifi which we did not have. One of the best sheets on my room was very dirty and had cuts in it. Mind you the sheet was in-between the other two sheets but and not noticeable till you separated them, however how hard is it to replace the throw like blanket if it's damaged and is stained. I can't speak for the other rooms since I stayed in the master bathroom. Everything else looked clean and maintained and everything was working besides the advertised wifi and the front desk...
Villas At Regal Palms

Leisure Lounge

3.0 star property
9.0 out of 10, Wonderful, (7)
"The property was exactly what I needed...a room for a few nights. Nice and quiet. Other guests were friendly"
Leisure Lounge

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2060)
"Great property. Some internal nonfunctioning items. "
Bahama Bay Resort

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1328)
"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 AU$461
includes taxes & fees
2 Mar - 3 Mar
Encantada Resort Vacation Townhomes by IDILIQ

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (135)
"Clean and comfortable, food and shopping close by"
Formosa Valley Resort by UNE Homes

3 Miles to Disney! Themed Home FREE Heated Pool & Spa Theater Grill & 7 Bedrooms

10.0 out of 10, Exceptional, (173)
"As lovers of Disney, this home was well themed to our liking. The theater was our favorite because of the details in theming and the surround sound was crazy good. It was also nice to enjoy the hot tub after long days at the parks. The changing lights in the hot tub was also a plus. We also appreciated the washer and 2 dryers to be able to keep up with laundry. Our party of 11 had more than enough room to spread out and be comfortable. Would highly recommend "
3 Miles to Disney! Themed Home FREE Heated Pool & Spa Theater Grill & 7 Bedrooms

Marvelous Villa with Galactic Themed Bedroom at Encore

9.2 out of 10, Wonderful, (43)
"10/10 experience!"
Marvelous Villa with Galactic Themed Bedroom at Encore

Tempo Trek Lodgings

3.5 star property
7.2 out of 10, Good, (20)
"Goood Area"
The price is AU$170
includes taxes & fees
28 Feb - 1 Mar
Tempo Trek Lodgings

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (121)
"Amazing for families. Great location and amenities. "
Lifetime of Vacations Resort

Grand Lake Resort

3.0 star property
9.0 out of 10, Wonderful, (102)
"Only issue I had was that there wasn't a broom or many cleaning supplies located in the room"
Grand Lake 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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Other types of properties in Winter Haven you may be interested in

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
9.4 out of 10, Exceptional, (710)
"My husband and I stayed at this property with our 2 grandsons to go to Legoland. It is situated very close to Legoland, approximate 10 min walk,(saves a $30 parking fee at Legoland) felt very safe, good breakfast in the morning, friendly staff. Several restaurants nearby, also walkable. Free parking at the hotel. Our room was large and very clean. We enjoyed our stay very much and would stay here again."
The price is AU$276
includes taxes & fees
9 Mar - 10 Mar
Best Western Plus Winter Haven Inn & Suites 

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
7.0 out of 10, Good, (1002)
"Everyone was very nice!!"
The price is AU$181
includes taxes & fees
16 Feb - 17 Feb
Howard Johnson by Wyndham Winter Haven FL

The Grove Resort & Water Park Orlando

4.0 star property
8.0 out of 10, Very good, (6886)
""I had an excellent experience with this property. The agent provided exceptional service, making the entire process smooth and enjoyable. The unit itself was clean, well-maintained, and equipped with all the necessary amenities. Highly recommend this place for anyone looking for comfort and convenience!""
The price is AU$369
includes taxes & fees
17 Feb - 18 Feb
The Grove Resort & Water Park Orlando
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 128 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.