Winter Haven Holiday Rentals

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Holiday Rentals in Winter Haven

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5059)
"Property was spacious, quiet and clean. No complaints at all!"
The price is AU$280
includes taxes & fees
16 Jan - 17 Jan
Summer Bay Orlando by Exploria Resorts

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1133)
"The home that we rented was fully furnished and located right near the pool. Christmas was memorable for my family. We enjoyed our mini vacation. This has been the 4th house I have rented in Margaritaville. I had to do a little cleaning before settling in with family. Overall great spot for shopping, movies and dining out. I definitely will return real soon."
Margaritaville Resort Orlando Cottages by Rentyl

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1405)
"Close to the Disney Parks"
Vacation Village at Parkway

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1627)
"Overall we enjoyed our stay, it was very conveniently located to Disney Parks, house keeping was great, felt like we were at our home, private patio. Only thing that could be improved are the utensils, they are very cheap quality and melted the moment it touched hot pot. Pots, pans, plates, cups and silverware were of great quality, just bring your own utensils if you are going to cook a lot."
The Berkley, Orlando

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1201)
"amazing property. "
The price is AU$468
includes taxes & fees
5 Jan - 6 Jan
Reunion Resort & Golf Club

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2818)
"Very closed to all Disney parks, restaurants, stores which is a major plus! Property has everything we need for a family of 6. The hot tub was nice to come home to after a long day of walking! We had a lovely and pleasant stay! "
The price is AU$540
includes taxes & fees
13 Jan - 14 Jan
Regal Oaks Resort Vacation Townhomes by IDILIQ

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2051)
"The resort was amazing just the right size not to big not to small had quite a bit of things to do several different pools basketball court splash pad for the kids I wish it was by a pool or something I didn’t care for the man made beach it should just be called the sand pit or something because when I hear beach I think of water don’t get me wrong it was really nice my grandkids cried when we left after five hours so it was amazing but change the name and our HOME AWAY FROM was just that very...
Bahama Bay Resort

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1111)
"This is a nice, quiet, clean and convenient place to stay near Disney. It has plenty of room for a large family and more bathrooms than you could need! That said, the property is a bit tired and could use some updates and TLC. "
Magic Village Yards, Trademark Collection by Wyndham

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1318)
"The gate keeper was awesome. "
The price is AU$547
includes taxes & fees
5 Jan - 6 Jan
Encantada Resort Vacation Townhomes by IDILIQ

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (114)
"Amazing for families. Great location and amenities. "
The price is AU$220
includes taxes & fees
19 Jan - 20 Jan
Lifetime of Vacations Resort

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very good, (516)
"Great property. Very spacious. Quiet neighborhood and nice amenities. Small updates needed: cracked sensor for light in kitchen, patch work, tiling in master bathroom floor, etc… Place was very clean. Suggestion- turn down the fire alarm sensor. It kept going off when we would make toast or take food out of the oven. Had to open the windows and doors or turn the fan on to prevent the alarm from going off. Only concern was we experienced others using the trash can assigned to our unit. "
Villas At Regal Palms

Family-Friendly Home - 6 Mi to Disney!

9.2 out of 10, Wonderful, (24)
"Great stay with friends"
Family-Friendly Home - 6 Mi to Disney!

Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*

9.6 out of 10, Exceptional, (30)
"House was clean the pool was warm even though the weather was not. "
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*

Family house / 4 BD-2Baths (August promotion!! low rates for this month)

8.8 out of 10, Excellent, (23)
"As Milton barreled down on us we felt safe and comfortable . The owner checked in on us and made sure everything was ok. Thank you for making a stressful event better. Donna "
Family house / 4 BD-2Baths (August promotion!! low rates for this month)

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2242)
"Condo is spacious, beds aren’t comfortable but for the price it’s understandable. If they could change the mattress would be amazing! Pool area is really nice. "
Caribe Cove Resort

MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME

MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME

THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!

9.0 out of 10, Wonderful, (100)
"could have been cleaned better. plus closet door fell off in one room when trying to open. dangerous. glad it was me opening it and not my 3 year old granddaughter."
THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!

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"
The price is AU$319
includes taxes & fees
16 Jan - 17 Jan
Grand Lake Resort

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (133)
"Clean and comfortable, food and shopping close by"
Formosa Valley Resort by UNE Homes

Luxury 4 bedroom 3 bath pool Home 283

9.2 out of 10, Wonderful, (22)
"Great communication with host."
Luxury 4 bedroom 3 bath pool Home 283
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, (650)
"Hotel is very nice and clean. Beautiful amenities. The room was clean and spacious. Would definitely stay there again. "
The price is AU$247
includes taxes & fees
8 Jan - 9 Jan
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)
"Ok stay"
The price is AU$184
includes taxes & fees
5 Jan - 6 Jan
Howard Johnson by Wyndham Winter Haven FL

Holiday Inn Winter Haven, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (1002)
"We go here every time when we go to Legoland. And always never had an issue we love it there"
The price is AU$217
includes taxes & fees
5 Jan - 6 Jan
Holiday Inn Winter Haven, an IHG Hotel
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 130 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.