Winter Haven Holiday Rentals

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Holiday Rentals in Winter Haven

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, (5043)
"As seniors we much enjoyed our time there because of the above. Our room was very clean. The appliances were dated. Dishwasher leaked all over the floor and had to be replaced which was an inconvenience because it took up 3 hours of our time. Stove and fridge were older and probably should be replaced as well. Wished there was a full length mirror somewhere in condo so we could look at ourselves before we headed out. Thank you"
The price is S$228
includes taxes & fees
5 Jan - 6 Jan,2025
Summer Bay Orlando by Exploria Resorts
Margaritaville Resort Orlando Cottages by Rentyl
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1115)
"The resort, pools, and lodging was great. "
Margaritaville Resort Orlando Cottages by Rentyl
Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1401)
"El hotel está en un lugar muy bueno bien cerca de los parques , el hotel está muy limpio con muchas condiciones muy limpio y un muy buen precio "
Vacation Village at Parkway
The Berkley, Orlando
Lobby sitting area

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1616)
"Loved the location and friendly staff!"
The Berkley, Orlando
Reunion Resort & Golf Club
11 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1193)
"Great stay!"
The price is S$560
includes taxes & fees
26 Dec - 27 Dec
Reunion Resort & Golf Club
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, (2812)
"We liked the private patio and hot tub. The pool was nice and the lake was a pretty feature of the property. The people at the reception desk were very friendly."
The price is S$448
includes taxes & fees
23 Dec - 24 Dec
Regal Oaks 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, (1108)
"Best option "
Magic Village Yards, Trademark Collection by Wyndham
Bahama Bay Resort
Property grounds

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2045)
"Loved everything this property had will be booking again soon. "
Bahama Bay Resort
Lifetime of Vacations Resort
Lake

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (112)
"I loved the charming feel of the property. The rooms were very spacious and clean. The property was very well maintained and the staff was terrific "
The price is S$185
includes taxes & fees
12 Jan - 13 Jan,2025
Lifetime of Vacations Resort
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, (1315)
"We loved the location and the community amenities. House was nice, clean and exactly what we needed. "
The price is S$510
includes taxes & fees
23 Dec - 24 Dec
Encantada Resort Vacation Townhomes by IDILIQ
Villas At Regal Palms
Outdoor pool, pool loungers

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very good, (512)
"Pool area was well kept and the restaurant staff were great. "
Villas At Regal Palms
Caribe Cove Resort
Outdoor pool

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2241)
"Condo is spacious, beds aren’t comfortable but for the price it’s understandable. If they could change the mattress would be amazing! Pool area is really nice. "
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, (132)
"The place is beautiful, clean and Romy for a big family"
Formosa Valley Resort by UNE Homes
Grand Lake Resort
Outdoor pool, pool umbrellas, pool loungers

Grand Lake Resort

3.0 star property
9.0 out of 10, Wonderful, (101)
"The people at the property were great to deal with our whole stay. The grounds were nice and well maintained. Central to a lot of things we did while we visited. We are actually planning a 2 week stay in July. Love the property. Pool is nice. Lake is beautiful. "
The price is S$268
includes taxes & fees
12 Jan - 13 Jan,2025
Grand Lake Resort
The Azur Resort
View from room

The Azur Resort

4.0 star property
8.8 out of 10, Excellent, (23)
"Me in my family really enjoy our stay "
The Azur Resort
Summerville Vacation Homes by Columbia Management
Private kitchen

Summerville Vacation Homes by Columbia Management

4.0 star property
8.4 out of 10, Very good, (149)
"Highly recommended "
Summerville Vacation Homes by Columbia Management
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 
Desk, laptop workspace, blackout curtains, iron/ironing board

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
9.4 out of 10, Exceptional, (634)
"The front desk was so helpful and courteous the entire time very supportive. I would highly recommend."
The price is S$201
includes taxes & fees
23 Dec - 24 Dec
Best Western Plus Winter Haven Inn & Suites 
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, (1003)
"Nice"
The price is S$155
includes taxes & fees
24 Dec - 25 Dec
Howard Johnson by Wyndham Winter Haven FL
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, (1002)
"One night stay so no chance to review all facilities. Room was a good size / comfy bed / good shower / friendly staff / easy parking / multiple eateries in easy walking distance. Good price."
The price is S$190
includes taxes & fees
13 Jan - 14 Jan,2025
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.

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.