Winter Haven Holiday Rentals

Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Holiday Rentals in Winter Haven

Our top choices for Winter Haven holiday rentals

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2806)
"Lovely property will stay here everytime"
The price is S$144
includes taxes & fees
15 Sept - 16 Sept
Vacation Village at Parkway
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1585)
"Great place"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Summer Bay Orlando by Exploria Resorts
5 outdoor pools, pool umbrellas, pool loungers

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5605)
"I had a great stay "
The price is S$203
includes taxes & fees
31 Aug - 1 Sept
Summer Bay Orlando by Exploria Resorts
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1382)
"The best hotel "
The price is S$366
includes taxes & fees
28 Aug - 29 Aug
Reunion Resort & Golf Club
Magical Dreams
Outdoor pool

Magical Dreams

3.0 star property
10.0 out of 10, Exceptional, (1)
"estaba algo caliente pero nos contactamos con los encargados y nos solucionaron el problema "
The price is S$187
includes taxes & fees
28 Aug - 29 Aug
Magical Dreams
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1891)
"Beautiful, perfect for a family getaway"
The price is S$165
includes taxes & fees
14 Sept - 15 Sept
The Berkley, Orlando
Regal Oaks Resort Vacation Townhomes by IDILIQ
View from property

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2969)
"Excellent service and stay "
The price is S$406
includes taxes & fees
3 Sept - 4 Sept
Regal Oaks Resort Vacation Townhomes by IDILIQ
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (138)
"Great place, would definitely stay there again "
The price is S$163
includes taxes & fees
25 Sept - 26 Sept
Barefoot'n Resort Kissimmee Orlando
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, (1373)
"Very nice resort "
The price is S$364
includes taxes & fees
31 Aug - 1 Sept
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, (1145)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham
Grand Lake Resort
Dock

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (135)
"Always a great place to stay"
Grand Lake Resort
Lifetime of Vacations Resort
Lake view

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (144)
"Fairly quiet, beautiful view. We would 100% stay here again."
Lifetime of Vacations 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, (168)
"My children and I enjoyed our stay. This place is close to everything. The property managers responds within minutes for any inquires. You can also reach someone by phone at any hour. The home was very clean with everything you need! I would definitely recommend!"
The price is S$632
includes taxes & fees
28 Aug - 29 Aug
Formosa Valley Resort by UNE Homes
Barefoot Suites
Dock

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1764)
"We have stayed numerous times. We love the property and love staying across the street from Fun Spot. Its nice to be able to stroll out every evening, shop, dine and have some fun. The 2 bedroom was very nice, clean and super roomy! We will be back as usual."
Barefoot Suites
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, (151)
"Not enough parking "
Summerville Vacation Homes by Columbia Management
Royal Laguna Villas By Magical Memories
Lobby

Royal Laguna Villas By Magical Memories

3.5 star property
7.0 out of 10, Good, (2336)
"the apartment is comfortable and pleasant but the air conditioning does not work, there is only a ceiling fan in the main room and in the living room. They did not give us the card for the pool area and it was a problem to pay and get the lockbox code."
Royal Laguna Villas By Magical Memories
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
2 outdoor pools, open 8 AM to 10 PM, pool loungers

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

3.5 star property
9.2 out of 10, Wonderful, (484)
"Very nice hotel...Very safe and clean "
The price is S$169
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Villas At Regal Palms
Outdoor pool, pool loungers

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very good, (576)
"This was the 2nd time we’ve stayed at Regal Palms and will definitely be back again. "
Villas At Regal Palms
Caribe Cove Resort
Outdoor pool, a heated pool

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2257)
"We had a great family vacation "
Caribe Cove Resort
Champions Gate condos by UNE
2 outdoor pools

Champions Gate condos by UNE

4.0 star property
9.2 out of 10, Wonderful, (30)
"Beautiful grounds and great location "
The price is S$413
includes taxes & fees
28 Aug - 29 Aug
Champions Gate condos by UNE
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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Top Winter Haven Hotel Reviews

Comfort Suites Maingate East

Comfort Suites Maingate East

10/10 Excellent
"We had issue with rooms, they were very caring to change our room. Understanding staff. Night time reception agent was a gem and daytime manager also."
Alice 7-night trip
Posted 1 day ago
Comfort Suites Maingate East

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 144 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.