Winter Haven Holiday Rentals

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Holiday Rentals in Winter Haven

2 outdoor pools, a heated pool, pool loungers
Seralago Hotel & Suites Main Gate East
3.0 star property
5.2 out of 10, (5268)
"This hotel is one my family and I would usually book, however it has absolutely gone down hill fast. There is absolutely NO dining area on premises, zero ice machines, rust and mold in the rooms, and no coffee makers in any rooms. We had to go off property just to even get a meal or snack. Oh and housekeeping is done ONLY after you check out. So needless to say, we WON'T be staying here again."
The price is AU$99
includes taxes & fees
29 May - 30 May
Seralago Hotel & Suites Main Gate East
Exterior
Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (5936)
"Great for the price..nothing fancy but not to bad."
The price is AU$100
includes taxes & fees
5 June - 6 June
Ramada by Wyndham Kissimmee Gateway
5 outdoor pools
Summer Bay Orlando by Exploria Resorts
3.5 star property
8.4 out of 10, Very good, (4719)
"Our family have a great time "
The price is AU$260
includes taxes & fees
6 June - 7 June
Summer Bay Orlando by Exploria Resorts
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Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (843)
"great stay"
Margaritaville Resort Orlando Cottages by Rentyl
Aerial view
Vacation Village at Parkway
3.0 star property
8.2 out of 10, Very good, (1258)
"I stay at a lot of resorts in the area!! This is one of my favorites 👍"
Vacation Village at Parkway
Property amenity
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (1441)
"Good Service "
The price is AU$147
includes taxes & fees
30 May - 31 May
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1413)
"Nice and clean "
The Berkley, Orlando
Outdoor pool, pool loungers, lifeguards on site
Spectrum Resort Orlando
4.0 star property
9.2 out of 10, Wonderful, (192)
"Loved the place. Wished the pool was open longer. "
Spectrum Resort Orlando
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, (2669)
"Very nice place to stay "
The price is AU$431
includes taxes & fees
11 June - 12 June
Regal Oaks Resort Vacation Townhomes by IDILIQ
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1120)
"3 bedroom condo was clean spacious our part of the resort was quiet "
The price is AU$539
includes taxes & fees
7 June - 8 June
Reunion Resort & Golf Club
2 outdoor pools, pool umbrellas, pool loungers
Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
8.6 out of 10, Excellent, (1253)
"It was great besides no air conditioning upstairs where bedrooms are , even though they clean after you leave there should be a dust pan and mop to do cleaning while there "
The price is AU$398
includes taxes & fees
12 June - 13 June
Encantada Resort Vacation Townhomes by IDILIQ
Outdoor pool, pool umbrellas, pool loungers
Magic Village Yards, Trademark Collection by Wyndham
4.0 star property
9.2 out of 10, Wonderful, (1069)
"We stayed here because it is close to all the parks. Pleasantly surprised with the unit too. All new!"
Magic Village Yards, Trademark Collection by Wyndham
Lake
Lifetime of Vacations Resort
3.0 star property
9.0 out of 10, Wonderful, (82)
"Place is good Its a older place but its safe and in a great location. Staff is very nice and area is a hub for Disneyland merchandise. "
Lifetime of Vacations Resort
Fridge, microwave, oven, stovetop
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
10.0 out of 10, Exceptional, (11)
"This property was great for our quick trip to Disney. The host was very easy to contact with any questions we had."
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
Interior
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
9.8 out of 10, Exceptional, (12)
"The house was the perfect size and those beds. So comfy. The house is older but well maintained. Great communication with the host. We really felt safe and relaxed while we were there. Thank you again!!!"
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
Outdoor pool, pool loungers
Villas At Regal Palms
4.0 star property
8.4 out of 10, Very good, (462)
"Very nice place "
Villas At Regal Palms
Terrace/patio
Family house / 4 BD-2Baths (August promotion!! low rates for this month)
9.2 out of 10, Wonderful, (12)
"Wonderful place to stay. Excellent communication. Very accommodating to our requests. We enjoyed our stay. Thank you"
Family house / 4 BD-2Baths (August promotion!! low rates for this month)
A heated pool
MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME
MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME
Fridge, microwave, oven, stovetop
⭐⭐⭐⭐⭐Expansive family-friendly vacation home, themed rooms, water park, fitness
10.0 out of 10, Exceptional, (1)
"The home is wonderfully and creatively decorated. The kitchen. dining. tv.pool table area is great fun for being together. We had rain on our visit but the home is conducive to handle all of that. Great visit, wonderfully responsive manager. Thank you"
⭐⭐⭐⭐⭐Expansive family-friendly vacation home, themed rooms, water park, fitness
Private kitchen
THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!
9.2 out of 10, Wonderful, (97)
"We had a wonderful stay, and the host is very responsive and helpful. Great location close to Disney"
THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!
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See all available properties in 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.

Winter Haven Holiday Home Travel Info

Other types of properties in Winter Haven you may be interested in

Bar (on property)
Holiday Inn Winter Haven, an IHG Hotel
3.0 star property
8.8 out of 10, Excellent, (955)
"Excellent service from front desk and kitchen/restaurant staff. Definitely recommend it for your next trip."
The price is AU$171
includes taxes & fees
30 May - 31 May
Holiday Inn Winter Haven, an IHG Hotel
Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room)
Best Western Plus Winter Haven Inn & Suites 
2.5 star property
9.4 out of 10, Exceptional, (343)
"My son is handicapped and the room was large are clean!"
The price is AU$214
includes taxes & fees
4 June - 5 June
Best Western Plus Winter Haven Inn & Suites 
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, (1003)
"Breakfast was good coffee good rooms are spacious and pool was nice n warm"
The price is AU$178
includes taxes & fees
30 May - 31 May
Howard Johnson by Wyndham Winter Haven FL
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.

Everything you need to know about Winter Haven holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Haven holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Haven holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winter Haven holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Haven. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Haven holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Haven holiday rentals we have selected for you start as low as AU$71 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winter Haven rentals

At Expedia, we put the best Winter Haven holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winter Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Haven holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

How many holiday rentals are there in Winter Haven?

Choose from 102 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.

Recent reviews of Winter Haven properties
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