Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Winter Haven vacation rentals

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, (3 reviews)
"Great location. Great communication with host. "
United States
Reid
The price is ￥9,988
￥39,790 total
includes taxes & fees
May 18 - May 19
BlockHaven near Legoland & Disney
House (4 Bedrooms) | Interior

Legoland & Lakes Pool Home Pet Friendly

Legoland & Lakes Pool Home Pet Friendly
3.0 star property
Winter Haven
The price is ￥24,912
￥85,881 total
includes taxes & fees
May 12 - May 13
Legoland & Lakes Pool Home Pet Friendly
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, (193 reviews)
"Was probably once a great time place. Owner was nice. Night time neighborhood is a bit noisy guess it's just how people act now no respect for property."
United States
wade
The price is ￥11,945
￥13,377 total
includes taxes & fees
Jun 11 - Jun 12
Lake Ida Beach Resort
House (3 Bedrooms) | Interior

Hook, Line & Leisure: Lakefront Gem w/ Porch!

Hook, Line & Leisure: Lakefront Gem w/ Porch!
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 ￥26,792
￥68,666 total
includes taxes & fees
May 12 - May 13
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Outdoor pool

Affordable Stays Kissimmee

Affordable Stays Kissimmee
2.5 star property
Kissimmee
The price is ￥8,665
￥33,252 total
includes taxes & fees
May 17 - May 18
Affordable Stays Kissimmee
Outdoor pool

Harmony Ensuite Room Shared Home No Car

Harmony Ensuite Room Shared Home No Car
2.5 star property
Kissimmee
The price is ￥6,618
￥30,929 total
includes taxes & fees
Jun 11 - Jun 12
Harmony Ensuite Room Shared Home No Car
House | 3 bedrooms

Super YES - Many Amenities Relax GYM Courts

Super YES - Many Amenities Relax GYM Courts
2.0 star property
Kissimmee
The price is ￥9,823
￥48,920 total
includes taxes & fees
Jun 2 - Jun 3
Super YES - Many Amenities Relax GYM Courts
Full-size fridge, microwave, oven, stovetop

VedaHive Luxury Villa

VedaHive Luxury Villa
3.0 star property
Solterra Resort
7.0 out of 10, Good, (10 reviews)
"Room was clean, place was nice and quiet. "
United States
Abi
The price is ￥7,051
￥27,231 total
includes taxes & fees
May 13 - May 14
VedaHive Luxury Villa
Exterior

King Ensuite Private Bath Shared Home

King Ensuite Private Bath Shared Home
2.0 star property
Solterra Resort
The price is ￥10,474
￥21,132 total
includes taxes & fees
May 12 - May 13
King Ensuite Private Bath Shared Home
House (3 Bedrooms) | Living area | TV

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is ￥13,739
￥61,320 total
includes taxes & fees
May 12 - May 13
Serenity - Family & Pet Friendly, Amazing Location
Interior entrance

Family Friendly Davenport Pool Villa

Family Friendly Davenport Pool Villa
4.0 star property
Florida Pines
The price is ￥28,202
￥89,320 total
includes taxes & fees
May 12 - May 13
Family Friendly Davenport Pool Villa
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 ￥14,494
￥85,055 total
includes taxes & fees
May 12 - May 13
Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse
Exterior

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,097 reviews)
"Fanily friendly, great value, great location!"
United States
Marivette
The price is ￥14,133
￥19,958 total
includes taxes & fees
May 14 - May 15
Vacation Village Orlando, Celebration
Lobby

Elita Inn

Elita Inn
3.0 star property
Dundee
7.4 out of 10, Good, (29 reviews)
"Very nice accommadations..friendly staff"
United States
lance
The price is ￥12,534
￥14,039 total
includes taxes & fees
Jun 9 - Jun 10
Elita Inn
Floor plan

Bright 3BR Resort Condo Near Disney + Pools

Bright 3BR Resort Condo Near Disney + Pools
3.0 star property
Davenport
The price is ￥16,702
￥58,659 total
includes taxes & fees
Jun 7 - Jun 8
Bright 3BR Resort Condo Near Disney + Pools
Outdoor pool

Aster Cove

Aster Cove
4.0 star property
Crescent Lakes
The price is ￥28,631
￥91,029 total
includes taxes & fees
May 12 - May 13
Aster Cove
House | Living area | 55-inch Smart TV with digital channels

Sunny Private Pool & Spa & Fenced Yard. Nr Parks

Sunny Private Pool & Spa & Fenced Yard. Nr Parks
4.5 star property
Indian Point
The price is ￥29,330
￥91,861 total
includes taxes & fees
May 29 - May 30
Sunny Private Pool & Spa & Fenced Yard. Nr Parks
Apartment (3 Bedrooms) | Interior

Condo With Sauna, Games, Poolnear Disney

Condo With Sauna, Games, Poolnear Disney
3.0 star property
Winter Garden
The price is ￥13,945
￥41,953 total
includes taxes & fees
Jun 3 - Jun 4
Condo With Sauna, Games, Poolnear Disney
Family Apartment | Dining room

Beautiful Luxury Apartment - Close to Disney

Beautiful Luxury Apartment - Close to Disney
3.0 star property
Kissimmee
The price is ￥16,010
￥74,281 total
includes taxes & fees
Jun 11 - Jun 12
Beautiful Luxury Apartment - Close to Disney
Interior

Tropical Retreat - Resort&spa - 15 Min to Disney!

Tropical Retreat - Resort&spa - 15 Min to Disney!
3.5 star property
Bahama Bay
The price is ￥13,863
￥55,381 total
includes taxes & fees
May 14 - May 15
Tropical Retreat - Resort&spa - 15 Min to Disney!
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

Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"Wonderful stay"
Deborah 4-night trip
Posted 1 hour ago
Delta Hotels by Marriott Orlando Celebration

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 54 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 Rotary Park are a couple of great spots to enjoy the outdoors. Winter Haven City Tennis Center and Theatre Winter Haven 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.