Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Winter Haven vacation rentals

House (3 Bedrooms) | Interior

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 reviews)
"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 ￥26,112
￥66,923 total
includes taxes & fees
Feb 16 - Feb 17
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"House was great, perfect central location. Very quiet neighborhood nice farm outside peaceful back yard seating area. "
United States
Wade
The price is ￥11,682
￥40,961 total
includes taxes & fees
Mar 1 - Mar 2
BlockHaven near Legoland & Disney
Outdoor pool, pool umbrellas, sun loungers

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (188 reviews)
"We have stayed here several times. "
United States
Martha
The price is ￥11,453
￥12,827 total
includes taxes & fees
Feb 16 - Feb 17
Lake Ida Beach Resort
Exterior

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.4 out of 10, Good, (1,008 reviews)
"Staff was very helpful, location was what we needed and rooms and pool were outstanding "
United States
Chester Joseph
The price is ￥10,842
￥15,771 total
includes taxes & fees
Feb 23 - Feb 24
voco Kissimmee Orlando by IHG
Marina

Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (197 reviews)
"Nice rooms helpful staff would go again for sure"
United States
David
Camp Mack Lodge, Marina & RV Resort
2 outdoor pools

Oasis Private Ensuite Room Shared Home

Oasis Private Ensuite Room Shared Home
3.5 star property
Kissimmee
The price is ￥8,974
￥21,452 total
includes taxes & fees
Feb 23 - Feb 24
Oasis Private Ensuite Room Shared Home
Exterior

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,347 reviews)
"Yes .. very clean rooms and hotel chef was great"
United States
Alicia
The price is ￥12,987
￥18,557 total
includes taxes & fees
Mar 9 - Mar 10
Vacation Village Orlando, Celebration
Townhome, 3 Bedrooms | Pool | A heated pool

Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse

Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse
3.5 star property
Kissimmee
The price is ￥23,875
￥96,616 total
includes taxes & fees
Feb 16 - Feb 17
Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse
Full-size fridge, microwave, oven, stovetop

Leisure Lounge

Leisure Lounge
3.5 star property
Solterra Resort
8.4 out of 10, Very Good, (17 reviews)
"The room was so nice! Very clean and in tact."
United States
Amber Carchelle
The price is ￥6,597
￥17,651 total
includes taxes & fees
Mar 18 - Mar 19
Leisure Lounge
Exterior

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (202 reviews)
"Great place. Great location. "
United States
Andrew
The price is ￥15,200
￥19,157 total
includes taxes & fees
Feb 25 - Feb 26
Barefoot'n Resort Kissimmee Orlando
House | 5 bedrooms

Mickey s Villa - Child-friendly Game Room Pool Spa

Mickey s Villa - Child-friendly Game Room Pool Spa
2.0 star property
Kissimmee
The price is ￥22,063
￥81,052 total
includes taxes & fees
Feb 23 - Feb 24
Mickey s Villa - Child-friendly Game Room Pool Spa
Outdoor pool, pool umbrellas, sun loungers

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,826 reviews)
"Great place. To stay "
United States
THOMAS
Barefoot Suites
Outdoor pool

Magical Dreams

Magical Dreams
4.0 star property
Kissimmee
5.4 out of 10, (16 reviews)
"Overall was a good stay . "
United States
Sorina
The price is ￥10,209
￥21,986 total
includes taxes & fees
Mar 18 - Mar 19
Magical Dreams
Lobby

Elita Inn

Elita Inn
3.0 star property
Dundee
7.6 out of 10, Good, (25 reviews)
"Very nice accommadations..friendly staff"
United States
lance
The price is ￥11,972
￥13,408 total
includes taxes & fees
Mar 16 - Mar 17
Elita Inn
Property amenity

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, (529 reviews)
"It was lovely! We would stay here again for sure! "
United States
Hilary
The price is ￥19,088
￥24,116 total
includes taxes & fees
Feb 24 - Feb 25
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Interior entrance

Jade Manor

Jade Manor
2.5 star property
Solterra Resort
8.8 out of 10, Excellent, (3 reviews)
"Amazing "
United States
Nilda
The price is ￥9,162
￥20,523 total
includes taxes & fees
Feb 21 - Feb 22
Jade Manor
Exterior

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, (3,063 reviews)
"Overall the stay was great. Staff were very helpful. We had some issues with the room carpet but it was taken care of as soon as I reported to the front desk. I very much recommend this place."
United States
Lucia
Regal Oaks Resort Vacation Townhomes by IDILIQ
Townhome, 6 Bedrooms | Interior

Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse

Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse
3.0 star property
Loughman
The price is ￥20,263
￥126,252 total
includes taxes & fees
Feb 16 - Feb 17
Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse
Comfort House, Multiple Bedrooms, Private Pool, Lakeside | In-room dining

FL- 1904 Nice Ct

FL- 1904 Nice Ct
3.0 star property
Kissimmee
The price is ￥28,250
￥77,874 total
includes taxes & fees
Feb 16 - Feb 17
FL- 1904 Nice Ct
Outdoor pool

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
3.0 star property
Kissimmee
The price is ￥22,166
￥43,261 total
includes taxes & fees
Mar 2 - Mar 3
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
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
"The hotel's children's play facilities were fantastic, and the kids had a blast! It's also very close to Disney's Animal Kingdom! We'll definitely stay at this hotel again!"
Bin 1-night trip
Posted 13 hours ago
Kompose Boutique Resort at Theme Parks

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 66 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.