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, (5254)
"Excellent stay. Thank you"
The price is NZ$77
per night
21 May - 22 May
Seralago Hotel & Suites Main Gate East
Exterior
Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (5906)
"My trip was awesome and the location was perfect "
The price is NZ$82
per night
20 May - 21 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)
"Great stay "
The price is NZ$234
per night
21 May - 22 May
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, (837)
"We stayed in one of the two bedroom villas. It actually had a third room with a bed as well (just no door) which was a nice surprise! The villa was incredibly clean, spacious and beautiful! It does have most of what you need but found a couple things could have been added such as a broom to sweep up after dinner etc. (we did call and ask for one, and they did deliver us a broom) and there were no dish cloths. Other than that, it had everything you need to cook etc. The property is huge,...
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)
"The hotel was what I expected… the only thing I saw that could have been better is mold growing in the shower…. For the price I was satisfied "
The price is NZ$159
per night
23 May - 24 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)
"Close to Disney, nice small hotel. Rooms were exactly as described, super comfortable for a family of 5. Checkout is strict but we had a late flight and they were great about accommodating us after check out time with parking. "
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)
"Over all I was very pleased with this property and would stay here again. The grounds were nicely maintained. Nice family friendly pool area. The condo we had was better than I expected with plenty room for our 6 but could easy do 8 comfortably. Plenty of table seating for a large family both inside and on the patio. Small minor issue I had ( tho I feel it was just lack of someone bringing it to the front desk attention) was a large water stain in the ceiling under the master bath which is...
The price is NZ$203
per night
12 Jun - 13 Jun
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 NZ$465
per night
1 Jun - 2 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 NZ$192
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)
"I have stayed here multiple times. Hotel staff are always friendly and helpful rooms are always clean have a jet tub and full kitchen. hotel also has pool,tiki area, paddle boats on the lake, bbq areas w. Picnic tables , kids playset and more to makevthe stay a little more enjoyable . "
Lifetime of Vacations Resort
Fridge, microwave, oven, stovetop
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
9.8 out of 10, Exceptional, (10)
"We come every year for the cheerleading tournament, very safe, gated neighborhood, very responsive owner for any issues, and the only house in the last 6 years where the a/c was actually cold the entire stay!!!"
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
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.

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

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, (331)
"Overnight stay for a volleyball tournament. Wish we had more time to enjoy the room and Amenities. "
The price is NZ$206
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 NZ$192
per night
23 May - 24 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 NZ$185
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winter Haven holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winter Haven. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winter Haven. Seeing all the best attractions is bound to make you fall in love with Winter Haven. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winter Haven short-term rentals, that won’t be hard to do.

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