Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

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, (2927)
"Clean rooms and wonderful staff"
The price is ￥13,606
￥17,989 total
includes taxes & fees
Oct 1 - Oct 2
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, (1638)
"Great place to stay."
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, (5637)
"Great view perfect location "
The price is ￥16,049
￥22,762 total
includes taxes & fees
Oct 1 - Oct 2
Summer Bay Orlando by Exploria Resorts
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1924)
"Great stay!"
The price is ￥16,870
￥20,665 total
includes taxes & fees
Oct 29 - Oct 30
The Berkley, Orlando
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1404)
"Great place for the family "
Reunion Resort & Golf Club
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, (2982)
"Loved the location of the property and that the property was gated"
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, (1381)
"Very nice resort "
Encantada Resort Vacation Townhomes by IDILIQ
Magical Dreams
Outdoor pool

Magical Dreams

4.0 star property
10.0 out of 10, Exceptional, (1)
"estaba algo caliente pero nos contactamos con los encargados y nos solucionaron el problema "
The price is ￥10,142
￥21,632 total
includes taxes & fees
Oct 2 - Oct 3
Magical Dreams
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (144)
"Loved being able to walk across the street to Old Town. Large space and a great price. "
The price is ￥14,300
￥18,087 total
includes taxes & fees
Oct 5 - Oct 6
Barefoot'n Resort Kissimmee Orlando
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, (1146)
"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, (140)
"Amber was great we had a ball definitely coming back resort was beautiful "
Grand Lake Resort
Barefoot Suites
Dock

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1770)
"We have stayed numerous times. We love the property and love staying across the street from Fun Spot. Its nice to be able to stroll out every evening, shop, dine and have some fun. The 2 bedroom was very nice, clean and super roomy! We will be back as usual."
Barefoot Suites
Lifetime of Vacations Resort
Lake view

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (147)
"Quiet place "
Lifetime of Vacations Resort
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, (487)
"Very nice hotel...Very safe and clean "
The price is ￥15,547
￥19,682 total
includes taxes & fees
Oct 3 - Oct 4
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Formosa Valley Resort by UNE Homes
Private pool

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (170)
"Great stay"
Formosa Valley Resort by UNE Homes
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
Outdoor pool, a heated pool

Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool

9.6 out of 10, Exceptional, (48)
"The home was perfect for our family trip to Disney! Its conveniently located near all of the FUN!! Great place to stay! I would definitely stay here again!"
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
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
Summerville Vacation Homes by Columbia Management
Captiva-06 (SMV104) | Private kitchen | Fridge, microwave, oven, stovetop

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
Bahama Bay Resort
4 outdoor pools, pool umbrellas, sun loungers

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2089)
"It's a family place, were you feel comfortable and welcome."
The price is ￥30,416
￥41,543 total
includes taxes & fees
Oct 2 - Oct 3
Bahama Bay Resort
Encore Resort
Outdoor pool

Encore Resort

4.0 star property
6.4 out of 10, (117)
"Great place "
Encore 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.
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Top Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"I love I go back closed "
Reynol 2-night trip
Posted 13 hours ago
The Grove Resort & Water Park Orlando

Find out more about Winter Haven

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 129 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 Peppa Pig Theme Park Florida, 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.