Winter Haven Holiday Rentals

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Holiday Rentals in Winter Haven

Ramada by Wyndham Kissimmee Gateway
Exterior
Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, 5,976 reviews
"It was an old hotel but everything was clean , people around the property were nice.Very close to the parks.Only 10 minutes drive . The area around the hotel was very nice too. "
The price is S$89
per night
2 Jun - 3 Jun
Ramada by Wyndham Kissimmee Gateway
Summer Bay Orlando by Exploria Resorts
5 outdoor pools
Summer Bay Orlando by Exploria Resorts
3.5 star property
8.4 out of 10, Very good, 4,749 reviews
"👍"
The price is S$253
per night
2 Jun - 3 Jun
Summer Bay Orlando by Exploria Resorts
Seralago Hotel & Suites Main Gate East
2 outdoor pools, a heated pool, pool loungers
Seralago Hotel & Suites Main Gate East
3.0 star property
5.2 out of 10, 5,288 reviews
"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 S$88
per night
2 Jun - 3 Jun
Seralago Hotel & Suites Main Gate East
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Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
Property amenity
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
3.0 star property
7.8 out of 10, Good, 1,452 reviews
"I enjoyed my stay at the hotel on my girls trip memorial weekend.. The room was nice and roomy enough for 4.. My issue with this whole booking is the fact that Expedia states there is a car charger on site but there isn’t one.. That issue needs to be rectified as this is false advertisement to anyone like myself who rented a electric car and chose this hotel for that specific reason.."
The price is S$132
per night
9 Jun - 10 Jun
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
Margaritaville Resort Orlando Cottages by Rentyl
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, 847 reviews
"Nice, clean, and quiet. "
Margaritaville Resort Orlando Cottages by Rentyl
Vacation Village at Parkway
Aerial view
Vacation Village at Parkway
3.0 star property
8.2 out of 10, Very good, 1,268 reviews
"Rooms and facilities need updating"
Vacation Village at Parkway
The Berkley, Orlando
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, 1,417 reviews
"Nice and clean "
The Berkley, Orlando
Spectrum Resort Orlando
Outdoor pool, pool loungers, lifeguards on site
Spectrum Resort Orlando
4.0 star property
9.2 out of 10, Wonderful, 196 reviews
"Loved our stay. Great for families. We will be back again! "
Spectrum Resort Orlando
Regal Oaks Resort Vacation Townhomes by IDILIQ
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, 2,679 reviews
"The property was very clean and our townhome felt like home. "
The price is S$395
per night
16 Jun - 17 Jun
Regal Oaks Resort Vacation Townhomes by IDILIQ
Reunion Resort & Golf Club
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, 1,126 reviews
"Excellent service "
The price is S$482
per night
4 Jun - 5 Jun
Reunion Resort & Golf Club
Encantada Resort Vacation Townhomes by IDILIQ
2 outdoor pools, pool umbrellas, pool loungers
Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
8.6 out of 10, Excellent, 1,255 reviews
"The breaker flipped and the power went out in the middle of me cooking. But maintenance was there pretty swiftly to get the power restored."
The price is S$360
per night
18 Jun - 19 Jun
Encantada Resort Vacation Townhomes by IDILIQ
Magic Village Yards, Trademark Collection by Wyndham
Outdoor pool, pool umbrellas, pool loungers
Magic Village Yards, Trademark Collection by Wyndham
4.0 star property
9.2 out of 10, Wonderful, 1,071 reviews
"The location of this property and convenience is amazing "
The price is S$838
per night
1 Jul - 2 Jul
Magic Village Yards, Trademark Collection by Wyndham
Lifetime of Vacations Resort
Lake
Lifetime of Vacations Resort
3.0 star property
9.0 out of 10, Wonderful, 83 reviews
"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
Villas At Regal Palms
Outdoor pool, pool loungers
Villas At Regal Palms
4.0 star property
8.4 out of 10, Very good, 464 reviews
"Outstanding "
Villas At Regal Palms
Grand Lake Resort
Outdoor pool, pool umbrellas, pool loungers
Grand Lake Resort
3.0 star property
9.0 out of 10, Wonderful, 86 reviews
"Very courteous staff "
Grand Lake Resort
Bahama Bay Resort
Property grounds
Bahama Bay Resort
3.5 star property
8.6 out of 10, Excellent, 2,024 reviews
"We had a lower end 2 bedroom unit. Very spacious & updated nicely. We will definitely return to this resort. "
Bahama Bay Resort
Celebration Suites
3 outdoor pools, open 9:00 AM to midnight, pool umbrellas, pool loungers
Celebration Suites
3.0 star property
7.8 out of 10, Good, 4,056 reviews
"No need for the extra room but good if more people with you "
Celebration Suites
The Azur Resort
Living area
The Azur Resort
4.0 star property
8.4 out of 10, Very good, 15 reviews
"Enjoyed our stay…really nice "
The Azur Resort
Caribe Cove Resort
Outdoor pool
Caribe Cove Resort
3.5 star property
8.8 out of 10, Excellent, 2,227 reviews
"The salt water pool is heated. The mattresses were lumpy, shower in master bath wasn't useable, carpet is worn, ice dispenser stuck. In need of some updating but overall was a good value. Front desk people were great and super helpful. "
Caribe Cove Resort
Formosa Valley Resort by UNE Homes
Private pool
Formosa Valley Resort by UNE Homes
4.0 star property
9.4 out of 10, Exceptional, 115 reviews
"The space is very accommodating to families - lots of space for everyone to move around. The linens were clean and the beds were comfortable. My only concern was the unit number was missing from my confirmation so we had to call in to get that. Thankfully we got an answer right away! The other was the upstairs bathroom toilet seal needs replaced - it leaks and the ring around it was nasty."
Formosa Valley Resort by UNE Homes
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

Best Western Plus Winter Haven Inn & Suites 
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, 349 reviews
"Very nice clean property, in a great location , clean propery, rooms very spacious, "
The price is S$191
per night
9 Jun - 10 Jun
Best Western Plus Winter Haven Inn & Suites 
Holiday Inn Winter Haven, an IHG Hotel
Bar (on property)
Holiday Inn Winter Haven, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, 958 reviews
"The staff were really attentive and plesant. My husband really liked that they were very easy to access and ask for coffee. The water pressure was a little weak and there were cracks in door where it looks like someone had pounded on it in the bathroom. When I told front desk they offered to move us. It was really just cosmetic so we stayed put."
The price is S$176
per night
9 Jun - 10 Jun
Holiday Inn Winter Haven, an IHG Hotel
Howard Johnson by Wyndham Winter Haven FL
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, 1,003 reviews
"I've stayed here a couple of times, and I love the retro feel of this cute little roadside inn. It's been well-maintained and has such adorable vibes I had my friends come to visit and stay here, as well. It's not fancy, but it's roomy, clean, and fun."
The price is S$141
per night
17 Jun - 18 Jun
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.

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

Sonder Cirrus

Sonder Cirrus

5/5 Excellent
"Staff was great and gave us good Disney park tips. Conveniently located to theme parks and restaurants. Rooms were spacious and clean. The only thing that can use some improvement was the pool / hot tub. It needed some cleaning but other than that we will definitely recommend this place and will stay again. "
A verified traveller stayed at Sonder Cirrus
Posted 17 hours ago
Sonder Cirrus