Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Winter Haven vacation rentals

House (3 Bedrooms) | Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Cottage in Winter Haven

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
10.0 out of 10, Exceptional, (3)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
United States
John
The price is NT$5,375
NT$13,776 total
includes taxes & fees
Jan 3 - 2026/1/4
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Outdoor pool, pool umbrellas, sun loungers
Lake Ida Beach Resort

Cottage in Winter Haven

Lake Ida Beach Resort
3.0 star property
7.2 out of 10, Good, (187)
"We have stayed here several times. "
United States
Martha
The price is NT$2,672
NT$2,993 total
includes taxes & fees
Jan 15 - 2026/1/16
Lake Ida Beach Resort
Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors
BlockHaven near Legoland & Disney

Vacation Home in Winter Haven

BlockHaven near Legoland & Disney
3.5 star property
The price is NT$2,935
NT$9,025 total
includes taxes & fees
Jan 3 - 2026/1/4
BlockHaven near Legoland & Disney
Exterior
voco Kissimmee Orlando by IHG

Aparthotel in Kissimmee

voco Kissimmee Orlando by IHG
4.0 star property
7.6 out of 10, Good, (1011)
"Place was clean, staff great, cozy very nice area swimming pool"
United States
KRYSTLE
The price is NT$1,949
NT$2,926 total
includes taxes & fees
Jan 7 - 2026/1/8
voco Kissimmee Orlando by IHG
Interior
Margaritaville Cottages Orlando by Rentyl

Aparthotel in Kissimmee

Margaritaville Cottages Orlando by Rentyl
4.0 star property
8.8 out of 10, Excellent, (1759)
"Great place "
United States
Lauren
The price is NT$6,255
NT$13,392 total
includes taxes & fees
Jan 4 - 2026/1/5
Margaritaville Cottages Orlando by Rentyl
Aerial view
Vacation Village Orlando, Celebration

Condo in Kissimmee

Vacation Village Orlando, Celebration
3.0 star property
8.6 out of 10, Excellent, (3133)
"Great place to stay"
United States
Jose
The price is NT$2,753
NT$3,911 total
includes taxes & fees
Jan 12 - 2026/1/13
Vacation Village Orlando, Celebration
Desk, laptop workspace, free WiFi
Elita Inn

Aparthotel in Dundee

Elita Inn
3.0 star property
10.0 out of 10, Exceptional, (7)
"Very nice accommadations..friendly staff"
United States
lance
The price is NT$2,358
NT$2,640 total
includes taxes & fees
Dec 30 - Dec 31
Elita Inn
2 outdoor pools, open 8 AM to 10 PM, sun loungers
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Aparthotel in Davenport

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
9.2 out of 10, Wonderful, (508)
"Great place"
United States
Bobby
The price is NT$3,929
NT$4,964 total
includes taxes & fees
Jan 15 - 2026/1/16
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Billiards
Regal Oaks Resort Vacation Townhomes by IDILIQ

Condo resort in Kissimmee

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
8.4 out of 10, Very Good, (3037)
"Great accommodations, clean and very spacious. Highly recommend to others, especially families. Pool was lovely "
United States
Christopher
The price is NT$4,533
NT$11,353 total
includes taxes & fees
Jan 4 - 2026/1/5
Regal Oaks Resort Vacation Townhomes by IDILIQ
Dock
Barefoot Suites

Aparthotel in Kissimmee

Barefoot Suites
3.0 star property
9.0 out of 10, Wonderful, (1801)
"Clean room location "
United States
Bryan
Barefoot Suites
Full-size fridge, microwave, cookware/dishes/utensils, freezer
Jade Manor

Aparthotel in Solterra Resort

Jade Manor
2.5 star property
8.0 out of 10, Very Good, (2)
"Amazing "
United States
Nilda
The price is NT$1,886
NT$4,225 total
includes taxes & fees
Dec 30 - Dec 31
Jade Manor
Sauna
Harmony Haven

Aparthotel in Kissimmee

Harmony Haven
2.5 star property
4.0 out of 10, (1)
"It was loud and more like a rooming house there was a baby there who cried all the time I didn’t stay the last night we went so where else"
United States
Ciera
The price is NT$1,886
NT$4,281 total
includes taxes & fees
Jan 1 - 2026/1/2
Harmony Haven
Exterior
Barefoot'n Resort Kissimmee Orlando

Aparthotel in Kissimmee

Barefoot'n Resort Kissimmee Orlando
2.5 star property
9.0 out of 10, Wonderful, (179)
"Comfortable and clean room, good location."
United States
Karina
The price is NT$3,495
NT$4,359 total
includes taxes & fees
Jan 4 - 2026/1/5
Barefoot'n Resort Kissimmee Orlando
Private pool
Formosa Valley Resort by UNE Homes

Vacation Home in Kissimmee

Formosa Valley Resort by UNE Homes
4.0 star property
9.4 out of 10, Exceptional, (196)
"Loved our stay here. Would highly recommend "
United States
Walter
The price is NT$5,205
NT$15,956 total
includes taxes & fees
Jan 5 - 2026/1/6
Formosa Valley Resort by UNE Homes
Lobby
The Berkley, Orlando

Vacation Home in Kissimmee

The Berkley, Orlando
4.0 star property
9.6 out of 10, Exceptional, (2019)
"The location of the resort is great. The room was perfect for our group. Staff was great, pool, game room. We would stay again. "
United States
Sarha
The price is NT$4,783
NT$5,737 total
includes taxes & fees
Jan 4 - 2026/1/5
The Berkley, Orlando
Lobby
Disney's Animal Kingdom Villas - Kidani Village

Aparthotel in Bay Lake

Disney's Animal Kingdom Villas - Kidani Village
4.0 star property
9.0 out of 10, Wonderful, (166)
"The animals are amazing and the location for Animal Kingdom was perfect! The room was clean and comfortable."
United States
Kelly
Disney's Animal Kingdom Villas - Kidani Village
Lake
Camp Mack Lodge, Marina & RV Resort

Cabin in Lake Wales

Camp Mack Lodge, Marina & RV Resort
3.0 star property
9.0 out of 10, Wonderful, (191)
"We lived our stay and can't wait to come back soon"
United States
Ramona
The price is NT$3,558
NT$3,985 total
includes taxes & fees
Dec 30 - Dec 31
Camp Mack Lodge, Marina & RV Resort
House | 5 bedrooms
Super Cool- Sleeps 17 Newly Built Near Parks

Vacation Home in Kissimmee

Super Cool- Sleeps 17 Newly Built Near Parks
2.0 star property
The price is NT$2,809
NT$12,050 total
includes taxes & fees
Jan 25 - 2026/1/26
Super Cool- Sleeps 17 Newly Built Near Parks
Exterior
Davenport Vacation Homes by Shine FM

Vacation Home in Tuscan Hills

Davenport Vacation Homes by Shine FM
4.0 star property
8.4 out of 10, Very Good, (26)
"it was a great property to stay in!"
United States
Nancy
The price is NT$3,426
NT$7,567 total
includes taxes & fees
Jan 9 - 2026/1/10
Davenport Vacation Homes by Shine FM
Full-size fridge, microwave, oven, stovetop
Leisure Lounge

Aparthotel in Solterra Resort

Leisure Lounge
3.5 star property
8.4 out of 10, Very Good, (17)
"The room was so nice! Very clean and in tact."
United States
Amber Carchelle
The price is NT$1,415
NT$3,697 total
includes taxes & fees
Dec 30 - Dec 31
Leisure Lounge
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

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent
"Great customer service "
pablo 1-night trip
Posted 14 hours ago
Ramada by Wyndham Kissimmee Gateway

Find out more about Winter Haven

Search for holiday rentals in Winter Haven on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Haven using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winter Haven!

Frequently asked questions

Can I find a vacation rental in Winter Haven?

Yes, there are vacation rentals in Winter Haven close to LEGOLAND® Florida, or you can choose a more secluded option if you'd like a relaxing place to 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's the top vacation rental that Winter Haven has to offer?

The Berkley, Orlando: This vacation home rental outside of Winter Haven offers a furnished patio, a terrace, and a barbecue grill 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 vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Winter Haven?

Choose from 63 Expedia vacation rentals in Winter Haven for a memorable vacation.

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 vacation rentals like in Winter Haven?

Vacation rentals are private properties you can book for a few days or a quick weekend in Winter Haven. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.