Winter Haven Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 ￥6,072
￥35,780 total
includes taxes & fees
May 31 - Jun 1
BlockHaven near Legoland & Disney
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 ￥25,081
￥67,258 total
includes taxes & fees
May 18 - May 19
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Outdoor dining

Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!

Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
Winter Haven
10.0 out of 10, Exceptional, (53 reviews)
"It was pet friendly. "
United States
Ibia
The price is ￥23,573
￥56,278 total
includes taxes & fees
May 18 - May 19
Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
Exterior detail

Tiny Paradise

Tiny Paradise
Winter Haven
9.4 out of 10, Exceptional, (13 reviews)
"I have stayed on property a few times, first experience with tiny Paradise very quaint and clean enjoyed my stay."
United States
SUSAN
The price is ￥10,318
￥19,176 total
includes taxes & fees
May 18 - May 19
Tiny Paradise
Interior

Cozy 1 bedroom home in Winter Haven perfect for your getaway.

Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"Great get away for 2! Perfect size. Very clean and nicely decorated. The host was very responsive. Highly recommend this property. "
United States
Anonymous traveler
The price is ￥17,461
￥29,843 total
includes taxes & fees
May 18 - May 19
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Paper towels

Private/Spacious 1BR Central Near LegoLand 2 Miles

Private/Spacious 1BR Central Near LegoLand 2 Miles
Winter Haven
9.2 out of 10, Wonderful, (12 reviews)
"clean room"
United States
sandra
The price is ￥12,858
￥27,354 total
includes taxes & fees
May 18 - May 19
Private/Spacious 1BR Central Near LegoLand 2 Miles
Smart TV

Large Family Home, Legoland, Pet Friendly, 7 Beds

Large Family Home, Legoland, Pet Friendly, 7 Beds
Winter Haven
10.0 out of 10, Exceptional, (23 reviews)
"Everything was very nice and comfortable. "
United States
Gary B.
The price is ￥26,473
￥65,685 total
includes taxes & fees
May 18 - May 19
Large Family Home, Legoland, Pet Friendly, 7 Beds
Outdoor dining

The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia
Winter Haven
9.8 out of 10, Exceptional, (14 reviews)
"Nice location, comfortable stay."
United States
Karthik D.
The price is ￥19,049
￥47,209 total
includes taxes & fees
May 18 - May 19
The Old Haven - An Enduring Piece of Nostalgia
4 bedrooms, free WiFi, bed sheets

Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
Winter Haven
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful stay in Winter Haven for our family Legoland trip, including our dog!The house was spotless, cozy, and easily accommodated all of us.Close to the park, would definitely stay again."
United States
Oscar G.
The price is ￥14,223
￥45,107 total
includes taxes & fees
May 29 - May 30
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
TV

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
8.8 out of 10, Excellent, (5 reviews)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is ￥18,255
￥44,249 total
includes taxes & fees
May 18 - May 19
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
1 bedroom, WiFi, bed sheets

Cozy 1-Bedroom Retreat Near Downtown & Legoland

Cozy 1-Bedroom Retreat Near Downtown & Legoland
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥20,319
￥27,710 total
includes taxes & fees
May 30 - May 31
Cozy 1-Bedroom Retreat Near Downtown & Legoland
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 ￥12,226
￥13,693 total
includes taxes & fees
Jun 5 - Jun 6
Lake Ida Beach Resort
Outdoor dining

Serene, Cozy, Lakefront Home with Jacuzzi/hot tub and covered porch on the Lake!

Serene, Cozy, Lakefront Home with Jacuzzi/hot tub and covered porch on the Lake!
Winter Haven
9.4 out of 10, Exceptional, (6 reviews)
The price is ￥21,430
￥54,194 total
includes taxes & fees
May 20 - May 21
Serene, Cozy, Lakefront Home with Jacuzzi/hot tub and covered porch on the Lake!
Interior

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Cheerful 4 Bed, 3 Bath Home with Screened Pool
Winter Haven
9.8 out of 10, Exceptional, (28 reviews)
"Excellent location, house was immaculate and beautiful. We stayed over xmas and there was even a tree for us. Highly recommend this place and would stay here again. "
United States
Eli R.
The price is ￥29,367
￥68,481 total
includes taxes & fees
May 18 - May 19
Cheerful 4 Bed, 3 Bath Home with Screened Pool
Fridge, microwave, oven, stovetop

Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events

Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Winter Haven
9.8 out of 10, Exceptional, (32 reviews)
"The host was very attentive, and responsive to our questions and comments. "
United States
Matt O.
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
TV, fireplace

Spacious 4-bedroom house in pleasant Winter Haven with AC

Spacious 4-bedroom house in pleasant Winter Haven with AC
Winter Haven
9.6 out of 10, Exceptional, (4 reviews)
"An outstanding stay! The house was extremely clean, welcoming, and had all the amenities that made our family vacation unforgettable in our visit to Legoland park"
Mexico
Monica
The price is ￥23,494
￥69,014 total
includes taxes & fees
May 18 - May 19
Spacious 4-bedroom house in pleasant Winter Haven with AC
House (3 Bedrooms) | Interior

Winter Haven Retreat w/ Private Pool!

Winter Haven Retreat w/ Private Pool!
3.0 star property
Winter Haven
Winter Haven Retreat w/ Private Pool!
Fridge, microwave, oven, stovetop

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Winter Haven
9.8 out of 10, Exceptional, (12 reviews)
"Very clean, welcoming home, close to the Wedding Venue 650. Close to Legoland as well. Host was very kind and accommodating. Will definitely stay again when going to this area!!"
United States
Cheryl G.
The price is ￥19,843
￥47,226 total
includes taxes & fees
May 18 - May 19
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Smart TV, fireplace

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Winter Haven
9.6 out of 10, Exceptional, (4 reviews)
"Everything was very clean! "
United States
Emilly D.
The price is ￥25,287
￥41,498 total
includes taxes & fees
May 18 - May 19
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Fridge, microwave, stovetop, coffee/tea maker

Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven

Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
Winter Haven
The price is ￥13,493
￥22,992 total
includes taxes & fees
May 31 - Jun 1
Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Awesome place for the family! Not ghetto like the grove down the rd. Villas are well maintained and huge nothing is run down. No stench of weed which is a major plus! Pools are nice as well as the lazy river. If your looking for somewhere super family friendly this is the place !"
Richard 2-night trip
Posted 4 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

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:

  • 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 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. 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.