Winter Haven Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 17 - Aug 18
Tomorrow
Aug 18 - Aug 19
Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31

Vacation Rentals in Winter Haven

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2761)
"Good place to stay in "
The price is P4,759
P6,374 total
includes taxes & fees
Aug 25 - Aug 26
Vacation Village at Parkway
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1561)
"Great place"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Summer Bay Orlando by Exploria Resorts
5 outdoor pools, pool umbrellas, sun loungers

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5593)
"I had a great stay "
The price is P6,410
P9,015 total
includes taxes & fees
Aug 21 - Aug 22
Summer Bay Orlando by Exploria Resorts
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (136)
"Great place, would definitely stay there again "
The price is P6,235
P7,790 total
includes taxes & fees
Aug 18 - Aug 19
Barefoot'n Resort Kissimmee Orlando
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1375)
"The water park was amazing and family oriented."
Reunion Resort & Golf Club
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1880)
"Very nice property for family vacation)"
The price is P5,557
P6,900 total
includes taxes & fees
Aug 19 - Aug 20
The Berkley, Orlando
Regal Oaks Resort Vacation Townhomes by IDILIQ
View from property

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very Good, (2959)
"Great stay "
Regal Oaks Resort Vacation Townhomes by IDILIQ
Encantada Resort Vacation Townhomes by IDILIQ
2 outdoor pools, pool umbrellas, sun loungers

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1368)
"Love that there was a private as well as a community pool"
Encantada Resort Vacation Townhomes by IDILIQ
Magic Village Yards, Trademark Collection by Wyndham
Outdoor pool, pool umbrellas, sun loungers

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1144)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham
Grand Lake Resort
Dock

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (132)
"Always a great place to stay"
Grand Lake Resort
Lifetime of Vacations Resort
Lake view

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (143)
"Fairly quiet, beautiful view. We would 100% stay here again."
Lifetime of Vacations Resort
Formosa Valley Resort by UNE Homes
Private pool

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (165)
"We loved our stay in UNE HOMES! Very spacious, clean, bathroom in everyroom, big rooms, BIG KITCHEN! Will be back for sure."
Formosa Valley Resort by UNE Homes
Barefoot Suites
Dock

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1762)
"Location. Everything. Excelente.perfect"
Barefoot Suites
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
2 outdoor pools, open 8 AM to 10 PM, sun loungers

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

3.5 star property
9.2 out of 10, Wonderful, (483)
"Very nice hotel...Very safe and clean "
The price is P5,773
P7,333 total
includes taxes & fees
Aug 19 - Aug 20
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Champions Gate condos by UNE
2 outdoor pools

Champions Gate condos by UNE

4.0 star property
9.2 out of 10, Wonderful, (25)
"Lovely place "
Champions Gate condos by UNE
Summerville Vacation Homes by Columbia Management
Private kitchen

Summerville Vacation Homes by Columbia Management

4.0 star property
8.4 out of 10, Very Good, (151)
"Not enough parking "
Summerville Vacation Homes by Columbia Management
Royal Laguna Villas By Magical Memories
Lobby

Royal Laguna Villas By Magical Memories

3.5 star property
7.0 out of 10, Good, (2336)
"the apartment is comfortable and pleasant but the air conditioning does not work, there is only a ceiling fan in the main room and in the living room. They did not give us the card for the pool area and it was a problem to pay and get the lockbox code."
Royal Laguna Villas By Magical Memories
Encore Resort
Outdoor pool

Encore Resort

4.0 star property
6.4 out of 10, (117)
"Great place "
Encore Resort
Villas At Regal Palms
Outdoor pool, sun loungers

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very Good, (573)
"This was the 2nd time we’ve stayed at Regal Palms and will definitely be back again. "
Villas At Regal Palms
Bahama Bay Resort
4 outdoor pools, pool umbrellas, sun loungers

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2088)
"It's a family place, were you feel comfortable and welcome."
The price is P13,698
P18,710 total
includes taxes & fees
Aug 18 - Aug 19
Bahama Bay Resort
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.
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 Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent
"Very close to Theme Parks. Only complaint is that breakfast was not included and was out of our price range "
David 1-night trip
Posted 11 hours ago
Holiday Inn Resort Kissimmee by the Parks by IHG

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 144 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.