Winter Haven Vacation Rentals

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Vacation Rentals in Winter Haven

Ramada by Wyndham Kissimmee Gateway
3 out of 5
7470 W. Irlo Bronson Memorial Hwy., Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is $77 per night from Jun 13 to Jun 14
$77
per night
Jun 13 - Jun 14
Stay at this 3-star family-friendly aparthotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the breakfast and the clean ...
7/10 Good! (4,628 reviews)
Clean and comfortable
"The room was clean. Bed comfortable. We like staying here due to close proximity to the parks. Tower only."

Reviewed on Jun 5, 2023

Ramada by Wyndham Kissimmee Gateway
Summer Bay Orlando by Exploria Resorts
3.5 out of 5
17805 US Highway 192, Clermont, FL
Stay at this 3.5-star family-friendly condo in Clermont. Enjoy free WiFi, free parking, and 5 outdoor pools. Our guests praise the pool and the helpful staff ...
8.2/10 Very Good! (4,050 reviews)
"Perfect stay!"

Reviewed on Jun 5, 2023

Summer Bay Orlando by Exploria Resorts
Seralago Hotel & Suites Main Gate East
3 out of 5
5678 West Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is $56 per night from Jun 12 to Jun 13
$56
per night
Jun 12 - Jun 13
Stay at this 3-star family-friendly aparthotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the clean rooms and the overall ...
5.2/10 (4,516 reviews)
"The room needed to be up dated and painted and cleaned For the price it was find We asked for extra pillow and wash cloths and was told they didn’t have any"

Reviewed on May 30, 2023

Seralago Hotel & Suites Main Gate East

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Regal Villa With Private Pool And Lake And Conservation View Near Disney
Stay at this family-friendly vacation home in Kissimmee. Enjoy private pools, a water park, and WiFi. Our guests praise the pool in our reviews. Popular attractions ...
9.8/10 Exceptional! (37 reviews)
Excellent Property
"Just returned from another great stay at this vacation villa. Always receive prompt responses from the property owner...Roman. My family and I can't wait to book another stay. You won't be disappointed. It has everything you need. Just buy your groceries."

Reviewed on Aug 10, 2021

Regal Villa With Private Pool And Lake And Conservation View Near Disney
Holiday Inn Orlando SW - Celebration Area, an IHG Hotel
3 out of 5
5711 W Irlo Bronson Memorial Hwy, Kissimmee, FL, 34746
Fully refundable
The price is $67 per night from Jun 13 to Jun 14
$67
per night
Jun 13 - Jun 14
Stay at this 3-star family-friendly aparthotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (1,170 reviews)
"The only thing I did not like is that the place was not very clean, although the beds were very clean, it was not the case with the carpets and the bathroom floor and carpet in the corridors"

Reviewed on May 31, 2023

Holiday Inn Orlando SW - Celebration Area, an IHG Hotel
CLC Regal Oaks Resort Vacation Townhomes
4 out of 5
5780 Golden Hawk Way, Kissimmee, FL
The price is $189 per night from Jun 11 to Jun 12
$189
per night
Jun 11 - Jun 12
Stay at this 4-star business-friendly condo in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the bar in our reviews. ...
8.2/10 Very Good! (2,394 reviews)
"Townhouse was very clean, all areas clean. Pool was great and very clean. Very kid friendly. Will go again in a few weeks.."

Reviewed on Jun 1, 2023

CLC Regal Oaks Resort Vacation Townhomes
 Fabulous Large 4 bedrooms Regal Villa With Fantastic Pool & Internet & 3D TV
Stay at this family-friendly vacation home in Kissimmee. Enjoy private pools, a water park, and WiFi. Our guests praise the pool in our reviews. Popular attractions ...
9.8/10 Exceptional! (14 reviews)
Love this place
"My fourth time staying inch here. I love it."

Reviewed on May 4, 2023

Fabulous Large 4 bedrooms Regal Villa With Fantastic Pool & Internet & 3D TV
Margaritaville Resort Orlando Cottages by Rentyl
4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Stay at this 4-star spa aparthotel in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.4/10 Very Good! (499 reviews)
"Clean and spacious. Great size for a family of 5. Had everything we needed for our extended stay."

Reviewed on Apr 19, 2023

Margaritaville Resort Orlando Cottages by Rentyl
Villas At Regal Palms
4 out of 5
2700 Sand Mine Road Consolidated Resorts, Davenport, FL
Stay at this 4-star spa aparthotel in Davenport. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the comfy beds and the family amenities ...
8.2/10 Very Good! (374 reviews)
"I really like the pool area and around the property. It was great."

Reviewed on May 30, 2023

Villas At Regal Palms
Vacation Village at Parkway
3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
Stay at this 3-star family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 6 spa tubs. Our guests praise the convenient parking and the comfy ...
8.2/10 Very Good! (1,089 reviews)
"We have been staying at Vacation Village at Parkway for 17 years. Great condo type set up for families. You can have 1 or 2 bedroom. Every room always have a living room with pull out sofa, washer dryer, partial or full kitchens. Has great pools and amenities. Great location in Celebration. Close ..."

Reviewed on May 31, 2023

Vacation Village at Parkway
Reunion Resort & Golf Club
5 out of 5
7593 Gathering Drive, Kissimmee, FL
Stay at this 5-star luxury aparthotel in Kissimmee. Enjoy 11 outdoor pools, 7 restaurants, and a golf course. Our guests praise the helpful staff and the spacious ...
8.6/10 Excellent! (1,081 reviews)
"Good"

Reviewed on Apr 20, 2023

Reunion Resort & Golf Club
Celebration Suites
3 out of 5
5820 W Irlo Bronson Memorial Hwy, Kissimmee, FL
The price is $135 per night from Jun 26 to Jun 27
$135
per night
Jun 26 - Jun 27
Stay at this 3-star family-friendly aparthotel in Kissimmee. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the ...
7.6/10 Good! (3,969 reviews)
"Good areas, nice room and facilities."

Reviewed on May 31, 2023

Celebration Suites
The Berkley, Orlando
4 out of 5
8545 W. Irlo Bronson Highway, Kissimmee, FL
Stay at this 4-star family-friendly vacation home in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (1,252 reviews)
"This place is a hidden gem. We’ve stayed twice, and each time we were astonished by what we got for the price. We got a 3 bedroom unit with a full kitchen (with glassware, cookware, dinnerware, small appliances, etc.), a full sized washed and dryer, and a screened in porch for less than we would’ve ..."

Reviewed on May 22, 2023

The Berkley, Orlando
Magic Village Yards, Trademark Collection by Wyndham
4 out of 5
3151 Pantanal Lane, Kissimmee, FL
Stay at this 4-star aparthotel in Kissimmee. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the comfy rooms in our ...
9/10 Wonderful! (991 reviews)
"Enjoyed the property very much. The speed bumps at the gate seem a bit rough and excessive but other than that we would definitely return. Thanks"

Reviewed on May 15, 2023

Magic Village Yards, Trademark Collection by Wyndham
CLC Encantada Resort Vacation Townhomes
3 out of 5
3070-B Secret Lake Drive, Kissimmee, FL
The price is $118 per night from Jun 8 to Jun 9
$118
per night
Jun 8 - Jun 9
Stay at this 3-star family-friendly aparthotel in Kissimmee. Enjoy free parking, 2 outdoor pools, and 2 spa tubs. Our guests praise the comfy rooms in our reviews. ...
8.6/10 Excellent! (1,141 reviews)
"We love this resort! We stay every time we bring our children to disney!!"

Reviewed on May 28, 2023

CLC Encantada Resort Vacation Townhomes
Summerville Vacation Homes by Columbia Management
4 out of 5
2621 Sunrise Shores Drive, Kissimmee, FL
Stay at this 4-star family-friendly vacation home in Kissimmee. Enjoy free WiFi, free parking, and a free kid's club. Our guests praise the pool and the helpful ...
8.4/10 Very Good! (127 reviews)
"When we arrived, we were shocked... is this really OUR place?? It was fantastic! Bigger than expected, large bedrooms, large bathrooms, clean, everything looked very new. Communication with the property was great - they responded right away. Grocery, coffee, lots of restaurants nearby, and a short ..."

Reviewed on Jun 1, 2023

Summerville Vacation Homes by Columbia Management
Formosa Valley Resort by UNE Homes
4 out of 5
Formosa Vly Pl, Kissimmee, FL
Stay at this 4-star vacation home in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Disney's Animal Kingdom® Theme Park and ...
9.2/10 Wonderful! (57 reviews)
"Simply a great stay, the insect thing doesn't exist or the air problem that some mentioned. the place is sparkling clean super accessible to all places. the super comfortable bed. I would definitely select this house again."

Reviewed on Jun 2, 2023

Formosa Valley Resort by UNE Homes
Holiday Inn Club Vacations Orlando Breeze Resort, an IHG Hotel
3.5 out of 5
100 Orlando Breeze Circle, Davenport, FL
Fully refundable
The price is $115 per night from Jun 25 to Jun 26
$115
per night
Jun 25 - Jun 26
Stay at this 3.5-star family-friendly aparthotel in Davenport. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (262 reviews)
"Elevator was broken when we arrived. It was communicated to us. The next morning it was still broken and help was offered when we were leaving. The elevator was fixed before we left and we were notified. Overall an excellent experience."

Reviewed on May 31, 2023

Holiday Inn Club Vacations Orlando Breeze Resort, an IHG Hotel
5 Miles from Disney World (Free pool Heat)
Stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a water park. Our guests praise the helpful staff and the bathrooms ...
9/10 Wonderful! (105 reviews)
Amazing Stay and Welcome!
"This place is beautiful and has so room and space you wouldn't want to miss staying there! We had a very short stay, but overall our kids loved the place and especially the pool! We would come back again next time. Owners are also quick to respond! Thank you so much!"

Reviewed on May 24, 2023

5 Miles from Disney World (Free pool Heat)
Berkley Lake Townhomes
3 out of 5
1010 Park Ridge Cir, Kissimmee, FL
Stay at this 3-star condo in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the WiFi in our reviews. Popular attractions ...
8.8/10 Excellent! (347 reviews)
"Very good for the price close to good restaurant, excellent for a family with kids"

Reviewed on Apr 14, 2023

Berkley Lake Townhomes
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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.

Winter Haven Vacation Rental Travel Info

Other types of properties in Winter Haven you may be interested in

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
The Grove Resort & Water Park Orlando
Margaritaville Resort Orlando

Margaritaville Resort Orlando

4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Fully refundableReserve now, pay when you stay
Margaritaville Resort Orlando
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.

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 vacation rentals, private vacation homes, apartments, condos, resorts, cabins, villas, hotels. 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. Explore our selection of Florida accommodations

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 months, such as October or November. For more hustle and bustle, you may prefer to visit in July or August. 

Prices vary throughout the year. Winter is the cheapest time to visit, with Summer the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, the selection of Winter Haven vacation rentals we have selected for you on this page range between $56 per night and $202 per night. Entering your desired dates in the search wizard 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. Or explore even further and have a look at our vacation rentals in Key West, Panama City rentals or Destin accommodation rentals. 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 87 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 Bok Tower Gardens are a couple of great spots to enjoy the outdoors. Chain of Lakes Park and Eagle Ridge Mall 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.

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