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, 6,042 reviews
"We had a great time at your hotel. Will definitely stay there again next time!"
The price is S$112
includes taxes & fees
27 Jun - 28 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, 4,771 reviews
"This property is amazing and the staff will go the extra mile to make sure you’re comfortable and taken care of. Even the cleaners are happy and friendly. Definitely will be staying here while I’m in the Orlando area and you should too! "
The price is S$219
includes taxes & fees
30 Jun - 1 Jul
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, 5,307 reviews
"Everything alright "
The price is S$88
includes taxes & fees
16 Jun - 17 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, 1,467 reviews
"Excellent "
The price is S$132
includes taxes & fees
23 Jun - 24 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, 858 reviews
"There were 14 of us but it never felt like there were that many of us. The rooms were nice and having a bathroom for each room made it easy for everyone to get ready. We did love the community pool, but weather forced is in early, so having the one in the backyard was nice for the kids when the weather cleared up. The adults could relax while they went back in the water. Definitely would recommend it for large families to gather."
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, 1,276 reviews
"Everything was close to the resort "
Vacation Village at Parkway
The Berkley, Orlando
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, 1,427 reviews
"Staff very professional. "
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, 201 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, 2,690 reviews
"I really enjoyed how big the property was and how many bathrooms there were. I disliked how rude the front desk people and when I call for early check in no body can give me a simple answer. I wished it was also cleaner specially if they say you can’t check in yet cause their cleaning "
The price is S$460
includes taxes & fees
19 Jun - 20 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, 1,127 reviews
"Excellent service "
The price is S$482
includes taxes & fees
26 Jun - 27 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, 1,260 reviews
"Nice place and good a family stay"
The price is S$335
includes taxes & fees
26 Jun - 27 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, 1,074 reviews
"Magic Village Yards is great when traveling with family or large groups. The pricing is very reasonable for the amount of space. The living space is good and spacious. The kitchen is useful however the cooking utensils need replacing as well as the cookware (pans). The bedrooms are a good size and it appears the clean the carpet however this is my 3rd time staying at this property and I can honestly say that the carpet should be replaced. Even though it looks shampooed, the corners and edges are...
The price is S$820
includes taxes & fees
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, 84 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, 469 reviews
"The only negative is the property is dated. Apart from that, it was clean and very spacious. We were actually given a 4 bed when we only requested a 3 bed. The communal areas are great. We loved our stay"
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, 88 reviews
"Beautiful property with very spacious rooms. Will definitely stay again "
Grand Lake Resort
Bahama Bay Resort
Property grounds
Bahama Bay Resort
3.5 star property
8.6 out of 10, Excellent, 2,026 reviews
"I love the staff was friendly and helpful and the resort was close yo restaurants and shoppers "
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, 4,058 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, 117 reviews
"We loved the privacy and cleanliness! "
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, 378 reviews
"The front desk staff was top notch. The staff here was just very pleasant and polite. I gotta admit it’s something I’m not use to being from Miami fl. I showed up with my wife and 4 children and they made everyone feel just as important. I will for sure be back!!! "
The price is S$205
includes taxes & fees
1 Jul - 2 Jul
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, 973 reviews
"."
The price is S$164
includes taxes & fees
23 Jun - 24 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
"The noise was not the fault of the hotel, but the construction nearby. There was a termite in the bed but only one and there were no signs of termites anywhere else in the facility so maybe just checked the place out and left. "
The price is S$141
includes taxes & fees
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.

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 101 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 Inman 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

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

5/5 Excellent
"We had a great time at your hotel. Will definitely stay there again next time!"
A verified traveller stayed at Ramada by Wyndham Kissimmee Gateway
Posted 1 day ago
Ramada by Wyndham Kissimmee Gateway