Winter Haven Vacation Rentals

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Vacation Rentals in Winter Haven

Vacation Village Orlando, Celebration

3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3070)
"Great place to stay"
United States
Jose
$128 nightly
The price is $146
Dec 14 - Dec 15
Total with taxes and fees
Vacation Village Orlando, Celebration

Margaritaville Cottages Orlando by Rentyl

4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1729)
"Amazing accommodations "
Canada
Marina
$375 nightly
The price is $426
Nov 30 - Dec 1
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
Kissimmee
8.4 out of 10, Very Good, (3013)
" Clean room and a great staff"
United States
Victor
$271 nightly
The price is $308
Nov 30 - Dec 1
Total with taxes and fees
Regal Oaks Resort Vacation Townhomes by IDILIQ

The Berkley, Orlando

4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (1988)
"Recommended amazing stay."
United States
Elf
$147 nightly
The price is $165
Nov 30 - Dec 1
Total with taxes and fees
The Berkley, Orlando

Reunion Resort & Golf Club

5.0 star property
Reunion
8.8 out of 10, Excellent, (1428)
"Was amazing beautiful and is an special place to go with kids , we love it !! "
United States
Yamila
$341 nightly
The price is $387
Dec 9 - Dec 10
Total with taxes and fees
Reunion Resort & Golf Club

Barefoot'n Resort Kissimmee Orlando

2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (161)
"Enjoyed the closeness of Old Town Kissimmee"
United States
Mary
$96 nightly
The price is $109
Nov 30 - Dec 1
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
Kissimmee
9.2 out of 10, Wonderful, (1152)
"Easy check-in, clean room"
United States
THOMAS
Magic Village Yards, Trademark Collection by Wyndham

Magical Dreams

4.0 star property
Kissimmee
6.0 out of 10, (5)
"Parking can be an issue but as long as you communicate with the others, you’ll be alright. "
United States
Shana
$116 nightly
The price is $132
Nov 30 - Dec 1
Total with taxes and fees
Magical Dreams

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
Kissimmee
8.4 out of 10, Very Good, (1400)
"2nd time staying here safe to say this is our second home "
United States
Melanie
$264 nightly
The price is $300
Nov 30 - Dec 1
Total with taxes and fees
Encantada Resort Vacation Townhomes by IDILIQ

Grand Lake Resort

3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (153)
"Amber was great we had a ball definitely coming back resort was beautiful "
United States
TAIYLAR
Grand Lake Resort

Formosa Valley Resort by UNE Homes

4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (191)
"Overall a clean house, one of the best properties I’ve stayed in. "
United States
Cristian
$477 nightly
The price is $530
Dec 1 - Dec 2
Total with taxes and fees
Formosa Valley Resort by UNE Homes

Barefoot Suites

3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1794)
"Barefoot Suites is just an overall an awesome place to stay."
United States
Loretta
$81 nightly
The price is $92
Nov 30 - Dec 1
Total with taxes and fees
Barefoot Suites

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

3.5 star property
Davenport
9.2 out of 10, Wonderful, (497)
"Everything was excellent! "
United States
Laura
$86 nightly
The price is $97
Dec 19 - Dec 20
Total with taxes and fees
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Lifetime of Vacations Resort

3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (151)
"Very nice quiet place... very polite front desk personnel "
United States
Iliana
Lifetime of Vacations Resort

Summerville Vacation Homes by Columbia Management

4.0 star property
Kissimmee
8.4 out of 10, Very Good, (152)
"Not enough parking "
United States
Corey
Summerville Vacation Homes by Columbia Management

Harmony Haven

2.5 star property
Kissimmee
$109 nightly
The price is $124
Nov 30 - Dec 1
Total with taxes and fees
Harmony Haven

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

Kissimmee
9.6 out of 10, Exceptional, (48)
"Very nice property. The kids really enjoyed the themed rooms."
United States
Ahmed E.
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool

Jade Manor

2.5 star property
Solterra Resort
$119 nightly
The price is $134
Nov 30 - Dec 1
Total with taxes and fees
Jade Manor

Doppio Westside

4.0 star property
Davenport
9.4 out of 10, Exceptional, (24)
"My family loved our stay highly recommend for family vacation. I would stay here again in the future!"
United States
Myia
$362 nightly
The price is $411
Nov 30 - Dec 1
Total with taxes and fees
Doppio Westside

Landing Townhomes Davenport

4.0 star property
Davenport
8.8 out of 10, Excellent, (8)
"The stay was great absolutely loved it "
United States
Janei Chantel
Landing Townhomes Davenport
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

Find out more about Winter Haven

Everything you need to know about Winter Haven vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Haven vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Haven vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Haven. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Haven in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $92 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Haven rentals

At Expedia, we put the best Winter Haven vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Haven vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 65 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 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.