Holiday Rentals in Winter Haven

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Holiday Rentals in Winter Haven

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1180)
"This is our 3rd time staying here. We did not love this cottage as much as we did the others. Although each room had a bathroom there was not one outside the bedrooms. We had 6 people and there was limited seating & small living room area The master bathroom shower leaked all over the floor Wish we were told there was a hot tub do we could have brought bathing suits We liked that it was less than a 10 minute walk to the Salty Rim and the shuttle to the promenade was very quick & convenient"
Margaritaville Resort Orlando Cottages by Rentyl

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5119)
"Very nice property with several pools and activities. The mini apartment where I stayed was the smallest type of room available here and it was perfect for two. It had a sofa bed but would be crowded if that was being used as a bed. The small kitchen was decently equipped and great to have. chose this location because I wanted to be guaranteed a patio or balcony and I loved being able to use that for a little work on my laptop in the fresh air. The resort fees were a little more than I...
The price is €161
includes taxes & fees
3 Mar - 4 Mar
Summer Bay Orlando by Exploria Resorts

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1664)
"Lovely property but beware of the Alligators just outside the property grounds. Lots of beautiful birds to be seen. I saw woodpecker, crane, stork, cormorant, vulture and others, all on the property grounds. I wish I had brought my binoculars."
The price is €193
includes taxes & fees
4 Feb - 5 Feb
The Berkley, Orlando

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1428)
"Very staff, clean room and great pool and hot tub"
The price is €105
includes taxes & fees
16 Feb - 17 Feb
Vacation Village at Parkway

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1211)
"Quick stay. Everyone was great and check in was fast."
The price is €318
includes taxes & fees
2 Feb - 3 Feb
Reunion Resort & Golf Club

Holiday Inn Club Vacations Orlando Breeze Resort, an IHG Hotel

3.5 star property
9.4 out of 10, Exceptional, (405)
"Great place. With Sasha at the front desk was a very pleasant experience. She was friendly, knowledgeable, and overall professional. She was GREAT! Management material! "
The price is €175
includes taxes & fees
2 Feb - 3 Feb
Holiday Inn Club Vacations Orlando Breeze Resort, an IHG Hotel

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1682)
"Nice balcony. Whirlpool out of order."
The price is €110
includes taxes & fees
4 Feb - 5 Feb
Barefoot Suites

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2829)
"Our unit was very nice , plenty of room for the family. We had a few issues during our stay, but we contacted the front desk and they took care of every issues we had. "
The price is €348
includes taxes & fees
5 Feb - 6 Feb
Regal Oaks Resort Vacation Townhomes by IDILIQ

3 Miles to Disney! Themed Home FREE Heated Pool & Spa Theater Grill & 7 Bedrooms

10.0 out of 10, Exceptional, (173)
"As lovers of Disney, this home was well themed to our liking. The theater was our favorite because of the details in theming and the surround sound was crazy good. It was also nice to enjoy the hot tub after long days at the parks. The changing lights in the hot tub was also a plus. We also appreciated the washer and 2 dryers to be able to keep up with laundry. Our party of 11 had more than enough room to spread out and be comfortable. Would highly recommend "
3 Miles to Disney! Themed Home FREE Heated Pool & Spa Theater Grill & 7 Bedrooms

Champions Gate condos by UNE

4.0 star property
8.0 out of 10, Very good, (2)
"Very nice condo at a very good price yes especially for a family or for a larger group."
The price is €304
includes taxes & fees
2 Feb - 3 Feb
Champions Gate condos by UNE

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1114)
"Perfect for a large family"
Magic Village Yards, Trademark Collection by Wyndham

Marvelous Villa with Galactic Themed Bedroom at Encore

9.2 out of 10, Wonderful, (41)
"We stayed with my in laws and it was awesome. Pool was heated nicely enough that my mother in law could get in with her arthritis. The rooms were spacious and plenty for all."
Marvelous Villa with Galactic Themed Bedroom at Encore

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very good, (522)
"Very good, would book again"
Villas At Regal Palms

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2058)
"Units are in desperate need of updating. Mirrors, faucets, dishes, sofas, tvs. Worn and in bad shape. Tv in living area only 24”- way too small for a family. Booked king bed but had queen. Kitchen not fully stocked with cookware/ spatulas. Needs some TLC. 2 units - daughters unit had similar issues and had unacceptable cookware and dishwasher which were replaced. That unit needs some help also. "
Bahama Bay Resort

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (134)
"Clean and comfortable, food and shopping close by"
Formosa Valley Resort by UNE Homes

Leisure Lounge

3.0 star property
8.8 out of 10, Excellent, (6)
"Very nice"
Leisure Lounge

Tempo Trek Lodgings

3.5 star property
7.2 out of 10, Good, (19)
"I really liked the property the communication with the instructions were excellent. the place was clean quiet parking is good. The only observation I have is that on Friday there was people on the sidewallk talking with music and it was hard to sleep. I woke up at 2am and they were still there. I had to be at the airport on Saturday at 6/6:30am and it was hard to go back to sleep. Aside from that I had a very experience."
The price is €104
includes taxes & fees
2 Feb - 3 Feb
Tempo Trek Lodgings

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (118)
"Amazing for families. Great location and amenities. "
Lifetime of Vacations Resort

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1326)
"I recently stayed at Encantada Resort Vacation Townhomes by IDILIQ in Four Corners, Florida, from December 23 to January 2, and it was absolutely fantastic! The resort provided the perfect balance of relaxation and convenience. The townhome was spacious, clean, and well-maintained, with all the amenities we needed to feel at home. The fully equipped kitchen made it easy to prepare meals, and the private patio with a hot tub was an incredible touch for unwinding after a day of exploring. The...
The price is €302
includes taxes & fees
23 Feb - 24 Feb
Encantada Resort Vacation Townhomes by IDILIQ

Oakwood Oasis

2.0 star property
6.6 out of 10, (9)
"A perfectly decent, clean room with a clean private bathroom in a big house. The carpets are stained. The number of rules to follow is a little mind boggling."
Oakwood Oasis
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.
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Other types of properties in Winter Haven you may be interested in

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
9.4 out of 10, Exceptional, (683)
"Hotel is brand new and beautiful. Room is large, nice bathroom, very quiet. Excellent for the price! "
The price is €144
includes taxes & fees
2 Feb - 3 Feb
Best Western Plus Winter Haven Inn & Suites 

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
7.0 out of 10, Good, (1011)
"I was skeptical because of some of the reviews but I must say, we enjoyed our stay. It’s local to a lot of things to do. Parking was sufficient. The staff was pleasant, the rooms were nice and cozy, bathroom was clean, shower had pressure and was nice and hot, we also really enjoyed the balcony. The breakfast was basic but enough to satisfy plus they have vending machines with lots of goodies. Overall, I have nothing but good things to say. "
The price is €110
includes taxes & fees
5 Feb - 6 Feb
Howard Johnson by Wyndham Winter Haven FL

The Grove Resort & Water Park Orlando

4.0 star property
8.0 out of 10, Very good, (6837)
"Hello my name is Juan Triana I was staying from Friday the 24th to Sunday the 26 th in room 3531 where everything was excellent, I left some sunglasses in the room , I could keep them to pick them up Let me know please thanks"
The price is €220
includes taxes & fees
9 Feb - 10 Feb
The Grove Resort & Water Park Orlando
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 129 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.