Search Holiday Rentals in Winter Haven

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Top 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, (5254)
"Excellent stay. Thank you"
The price is £52
per night
19 May - 20 May
Seralago Hotel & Suites Main Gate East
Exterior
Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (5904)
"My trip was awesome and the location was perfect "
The price is £52
per night
19 May - 20 May
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, (4711)
"We loved all of the pool options as well as having so many amenities available on site. We enjoyed playing mini golf as well as doing various craft projects with the kids. The kids loved it so much that we want to stay again! "
The price is £139
per night
19 May - 20 May
Summer Bay Orlando by Exploria Resorts
Save an average of 15% on thousands of hotels when you're signed in
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (836)
"The food by the pool was delicious!"
Margaritaville Resort Orlando Cottages by Rentyl
Aerial view
Vacation Village at Parkway
3.0 star property
8.2 out of 10, Very good, (1254)
"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, (1438)
"Great service "
The price is £77
per night
29 May - 30 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, (1412)
"It is like living in your own home. Fully equipped kitchen. King size beds comfortable but the twin beds were not. The vacation home is very nice though. Close to a lot of restaurants.20 mins to Disney"
The Berkley, Orlando
Outdoor pool, pool loungers, lifeguards on site
Spectrum Resort Orlando
4.0 star property
9.2 out of 10, Wonderful, (191)
"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 £241
per night
28 May - 29 May
Regal Oaks Resort Vacation Townhomes by IDILIQ
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1119)
"Perfect for the family. "
The price is £256
per night
2 Jun - 3 Jun
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 £208
per night
12 Jun - 13 Jun
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, (1066)
"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!*
9.8 out of 10, Exceptional, (10)
"Great location awesome home Great for the kids"
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
Interior
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
10.0 out of 10, Exceptional, (11)
"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!
Terrace/patio
Family house / 4 BD-2Baths (August promotion!! low rates for this month)
9.2 out of 10, Wonderful, (12)
"We had a lovely stay in this luxurious villa. 2 of the beds were very hard, so that is something te keep in mind, but didn't bother us. We had some minor issues that were quickly resolved."
Family house / 4 BD-2Baths (August promotion!! low rates for this month)
Outdoor pool, pool loungers
Villas At Regal Palms
4.0 star property
8.4 out of 10, Very good, (460)
"This is a great place to stay. This was second time staying and definitely not my last. Can’t wait to come back. "
Villas At Regal Palms
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
A heated pool
MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME
MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME
Private kitchen | Fridge, microwave, oven, stovetop
THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!
9.2 out of 10, Wonderful, (96)
"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!!
Don't see what you're looking for?
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 Rental Travel Info

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

Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room) | Desk, laptop workspace, blackout curtains, iron/ironing board
Best Western Plus Winter Haven Inn & Suites 
2.5 star property
9.4 out of 10, Exceptional, (331)
"Overnight stay for a volleyball tournament. Wish we had more time to enjoy the room and Amenities. "
The price is £99
per night
19 May - 20 May
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, (1001)
"Customer Service was excellent and the property was clean "
The price is £93
per night
22 May - 23 May
Howard Johnson by Wyndham Winter Haven FL
Bar (on property)
Holiday Inn Winter Haven, an IHG Hotel
3.0 star property
8.8 out of 10, Excellent, (950)
"Great stay so far! Check in was perfect "
The price is £89
per night
19 May - 20 May
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.

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, apart-hotels, 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 favorite 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 depends 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 £52 per night. Entering your travel dates in the search wizard you might find 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
Expedia verified reviews