Winter Garden Holiday Rentals

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Holiday Rentals in Winter Garden

The View Studio Suites and Event Venue

3.0 star property
Orlando
8.4 out of 10, Very good, (1387)
"Nice breakfast, friendly staff, great location "
United States
Yessica
The price is NZ$134
includes taxes & fees
1 Dec - 2 Dec
The View Studio Suites and Event Venue

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
Orlando
9.2 out of 10, Wonderful, (2244)
"Clean fresh smelling room, real friendly staff, great atmosphere. Always love staying here"
United States
Alexander
Florida Hotel & Conference Center in the Florida Mall

Vacation Village Orlando, Celebration

3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3042)
"Great place to stay"
United States
Jose
The price is NZ$226
includes taxes & fees
1 Dec - 2 Dec
Vacation Village Orlando, Celebration

Lake Buena Vista Resort Village & Spa

4.0 star property
Orlando
8.4 out of 10, Very good, (9287)
"Great stay"
United States
Jessica
Lake Buena Vista Resort Village & Spa

Margaritaville Cottages Orlando by Rentyl

4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1711)
"Our favorite hotel!"
United States
Odanis
The price is NZ$718
includes taxes & fees
18 Nov - 19 Nov
Margaritaville Cottages Orlando by Rentyl

Floridays Resort Orlando

3.5 star property
International Drive District
8.6 out of 10, Excellent, (11576)
"Room was clean, great staff "
United States
Nora
The price is NZ$413
includes taxes & fees
19 Nov - 20 Nov
Floridays Resort Orlando

The Berkley, Orlando

4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (1976)
"This property meets ALL my needs and I'll continue to stay here when i visit Orlando. Always friendly staff when i arrive there! Looking forward to my next visit, next year."
United States
Julia
The price is NZ$271
includes taxes & fees
20 Nov - 21 Nov
The Berkley, Orlando

The Point Hotel & Suites

3.5 star property
Florida Center
8.0 out of 10, Very good, (3290)
"Great place to stay "
United States
Kevaughn
The price is NZ$278
includes taxes & fees
18 Nov - 19 Nov
The Point Hotel & Suites

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
Kissimmee
8.4 out of 10, Very good, (3009)
"Superb accommodation and an excellent location for the parks if you have hired a car. My only criticism was we had a huge cockroach in the house that we had to get rid of. "
United Kingdom
Jordan
The price is NZ$586
includes taxes & fees
30 Nov - 1 Dec
Regal Oaks Resort Vacation Townhomes by IDILIQ

The Point by Edge

4.0 star property
Florida Center
8.4 out of 10, Very good, (806)
"Nice hotel"
United States
Madhu Kumar
The price is NZ$147
includes taxes & fees
20 Nov - 21 Nov
The Point by Edge

Club Wyndham Cypress Palms

3.5 star property
Kissimmee
9.0 out of 10, Wonderful, (1847)
"clean, great staff nice area and well maintained"
United States
Sharon
Club Wyndham Cypress Palms

Reunion Resort & Golf Club

5.0 star property
Reunion
8.8 out of 10, Excellent, (1424)
"Was amazing beautiful and is an special place to go with kids , we love it !! "
United States
Yamila
The price is NZ$502
includes taxes & fees
9 Dec - 10 Dec
Reunion Resort & Golf Club

Blue Tree Resort at Lake Buena Vista

3.0 star property
Orlando
8.6 out of 10, Excellent, (1823)
"Suite was awesome for my mom, myself, and my 5 month old! Staff was super friendly and overall an incredible stay! "
United States
Lauren
Blue Tree Resort at Lake Buena Vista

Parc Corniche Condominium Suite Hotel

3.0 star property
International Drive District
8.0 out of 10, Very good, (2181)
"Room was nice and clean and the staff was professional and friendly."
United States
Kiki
The price is NZ$271
includes taxes & fees
18 Nov - 19 Nov
Parc Corniche Condominium Suite Hotel

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

Vista Cay Resort by Millenium at Universal Blvd

3.5 star property
Orlando
8.6 out of 10, Excellent, (1570)
"We enjoyed our stay. From the villa to the pools, everything was amazing. "
United States
Serena
Vista Cay Resort by Millenium at Universal Blvd

Barefoot'n Resort Kissimmee Orlando

2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (156)
"We love it here! This is the only place we come when we are visiting Disney! The people are so friendly, and the place is clean and super nice! "
United States
Erin
The price is NZ$257
includes taxes & fees
18 Nov - 19 Nov
Barefoot'n Resort Kissimmee Orlando

Magical Dreams

4.0 star property
Kissimmee
7.0 out of 10, Good, (4)
"Parking can be an issue but as long as you communicate with the others, you’ll be alright. "
United States
Shana
The price is NZ$228
includes taxes & fees
18 Nov - 19 Nov
Magical Dreams

WorldQuest Orlando Resort

4.0 star property
Orlando
8.4 out of 10, Very good, (4018)
"Very attentive staff and clean rooms. "
United States
Diana-Patricia
WorldQuest Orlando Resort

Club Wyndham Star Island

3.5 star property
Kissimmee
8.4 out of 10, Very good, (454)
"Nice place to stay with affordable price."
United States
Eneida
Club Wyndham Star Island
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 Garden Hotel Reviews

Find out more about Winter Garden

Everything you need to know about Winter Garden holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Garden holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Garden holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winter Garden holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Garden holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Garden holiday rentals we have selected for you start as low as NZ$134 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winter Garden rentals

At Expedia, we put the best Winter Garden holiday 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 Garden 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 Garden holiday.

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 Garden. 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 holiday rental in Winter Garden?

Yes, there are holiday rentals in Winter Garden close to Surfari Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Winter Garden speak highly of the fun-filled theme parks and array of shops. While you're here, grab a bite or have a drink at the top-notch restaurants.

What are some of the best holiday rentals that Winter Garden has to offer?

The Berkley, Orlando: This holiday home rental outside of Winter Garden offers a furnished patio, a terrace and a BBQ 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 holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Winter Garden?

With 37 Expedia holiday rentals, you're guaranteed to find just the right place for your Winter Garden stay.

What can I see and do in Winter Garden?

Family-friendly attractions include Surfari Water Park and Central Florida Railroad Museum, whereas Lake Louisa State Park and West Orange Trail are a couple of great spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are holiday rentals like in Winter Garden?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Garden. Holiday rentals feature amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.