Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Winter Haven holiday rentals

Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
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 RM694
RM1,779 total
includes taxes & fees
28 Dec - 29 Dec
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Outdoor pool, pool umbrellas, pool loungers
Lake Ida Beach Resort

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (187)
"We have stayed here several times. "
United States
Martha
The price is RM345
RM387 total
includes taxes & fees
15 Jan - 16 Jan 2026
Lake Ida Beach Resort
Living area
BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
The price is RM585
RM1,396 total
includes taxes & fees
6 Jan - 7 Jan 2026
BlockHaven near Legoland & Disney
Exterior
voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.4 out of 10, Good, (1005)
"Place was clean, staff great, cozy very nice area swimming pool"
United States
KRYSTLE
The price is RM251
RM377 total
includes taxes & fees
7 Jan - 8 Jan 2026
voco Kissimmee Orlando by IHG
Interior
Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1753)
"Great place "
United States
Lauren
The price is RM808
RM1,730 total
includes taxes & fees
4 Jan - 5 Jan 2026
Margaritaville Cottages Orlando by Rentyl
Aerial view
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3117)
"Great place to stay"
United States
Jose
Vacation Village Orlando, Celebration
Desk, laptop workspace, free WiFi
Elita Inn

Elita Inn

Elita Inn
3.0 star property
Dundee
10.0 out of 10, Exceptional, (5)
"Yes this is an awesome place and especially clen we loved it "
United States
Bryson
The price is RM291
RM326 total
includes taxes & fees
28 Dec - 29 Dec
Elita Inn
2 outdoor pools, open 8 AM to 10 PM, pool loungers
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
Davenport
9.2 out of 10, Wonderful, (506)
"Great place"
United States
Bobby
The price is RM506
RM639 total
includes taxes & fees
15 Jan - 16 Jan 2026
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Billiards
Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very good, (3036)
"Great accommodations, clean and very spacious. Highly recommend to others, especially families. Pool was lovely "
United States
Christopher
The price is RM586
RM1,466 total
includes taxes & fees
5 Jan - 6 Jan 2026
Regal Oaks Resort Vacation Townhomes by IDILIQ
Dock
Barefoot Suites

Barefoot Suites

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

Jade Manor

Jade Manor
2.5 star property
Solterra Resort
8.0 out of 10, Very good, (2)
"Amazing "
United States
Nilda
The price is RM243
RM544 total
includes taxes & fees
4 Jan - 5 Jan 2026
Jade Manor
Sauna
Harmony Haven

Harmony Haven

Harmony Haven
2.5 star property
Kissimmee
The price is RM243
RM551 total
includes taxes & fees
28 Dec - 29 Dec
Harmony Haven
Exterior
Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (178)
"Comfortable and clean room, good location."
United States
Karina
The price is RM450
RM561 total
includes taxes & fees
7 Jan - 8 Jan 2026
Barefoot'n Resort Kissimmee Orlando
Private pool
Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes
4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (195)
"Loved our stay here. Would highly recommend "
United States
Walter
The price is RM758
RM2,157 total
includes taxes & fees
4 Jan - 5 Jan 2026
Formosa Valley Resort by UNE Homes
Lobby
The Berkley, Orlando

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2013)
"Really great 2 bedroom, beautiful Room, Nice Pool and Landscape...Will definitely be back."
United States
Thomas
The price is RM616
RM739 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Berkley, Orlando
Lobby
Disney's Animal Kingdom Villas - Kidani Village

Disney's Animal Kingdom Villas - Kidani Village

Disney's Animal Kingdom Villas - Kidani Village
4.0 star property
Bay Lake
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

Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (190)
"We lived our stay and can't wait to come back soon"
United States
Ramona
Camp Mack Lodge, Marina & RV Resort
5 bedrooms
Super Cool- Sleeps 17 Newly Built Near Parks

Super Cool- Sleeps 17 Newly Built Near Parks

Super Cool- Sleeps 17 Newly Built Near Parks
2.0 star property
Kissimmee
The price is RM462
RM1,669 total
includes taxes & fees
16 Jan - 17 Jan 2026
Super Cool- Sleeps 17 Newly Built Near Parks
Exterior
Davenport Vacation Homes by Shine FM

Davenport Vacation Homes by Shine FM

Davenport Vacation Homes by Shine FM
4.0 star property
Tuscan Hills
8.4 out of 10, Very good, (26)
"it was a great property to stay in!"
United States
Nancy
The price is RM443
RM977 total
includes taxes & fees
8 Jan - 9 Jan 2026
Davenport Vacation Homes by Shine FM
Full-sized fridge, microwave, oven, stovetop
Leisure Lounge

Leisure Lounge

Leisure Lounge
3.5 star property
Solterra Resort
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 RM183
RM477 total
includes taxes & fees
28 Dec - 29 Dec
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Clean room and very spacious "
Martine 1-night trip
Posted 23 hours ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Haven

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

  • View our selection of featured holiday rentals in Winter Haven
  • Use the map to find apartments and other holiday homes in the Winter Haven neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Haven while they last

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

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 63 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.