Windermere Holiday Rentals

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Our top choices for Windermere holiday rentals

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,268 reviews)
"Nice place to stay"
Canada
dianne
The price is AU$180
includes taxes & fees
2 Feb - 3 Feb
Vacation Village Orlando, Celebration

The Point by Edge

The Point by Edge
4.0 star property
Florida Center
8.4 out of 10, Very good, (867 reviews)
"Great view, pleasant staff."
United States
Crystal
The price is AU$128
includes taxes & fees
3 Mar - 4 Mar
The Point by Edge

Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
4.0 star property
Orlando
8.8 out of 10, Excellent, (2,879 reviews)
"Very nice staff, good food. "
United States
Peter
The price is AU$404
includes taxes & fees
20 Feb - 21 Feb
Wyndham Grand Orlando Resort Bonnet Creek

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1,791 reviews)
"Cottage was very clean and easy check in close to all dining and shopping "
United States
Fernando
The price is AU$620
includes taxes & fees
2 Feb - 3 Feb
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.6 out of 10, Good, (1,000 reviews)
"Staff was very helpful, location was what we needed and rooms and pool were outstanding "
United States
Chester Joseph
The price is AU$139
includes taxes & fees
4 Feb - 5 Feb
voco Kissimmee Orlando by IHG

Floridays Resort Orlando

Floridays Resort Orlando
3.5 star property
International Drive District
8.6 out of 10, Excellent, (11,703 reviews)
"Great place for a vacation "
United States
Kevin
Floridays Resort Orlando

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very good, (3,059 reviews)
"Overall the stay was great. Staff were very helpful. We had some issues with the room carpet but it was taken care of as soon as I reported to the front desk. I very much recommend this place."
United States
Lucia
Regal Oaks Resort Vacation Townhomes by IDILIQ

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,813 reviews)
"We have a great stay. Beautiful, clean rooms, big and spacious. Friendly staff at check-in."
United States
Barry
Barefoot Suites

The View Studio Suites and Event Venue

The View Studio Suites and Event Venue
3.0 star property
Orlando
8.4 out of 10, Very good, (1,594 reviews)
"Clean and spacious rooms and the breakfast was great."
United States
Karen
The price is AU$136
includes taxes & fees
3 Mar - 4 Mar
The View Studio Suites and Event Venue

WorldQuest Orlando Resort

WorldQuest Orlando Resort
4.0 star property
Orlando
8.4 out of 10, Very good, (4,042 reviews)
"Clean room and amenities, helpful staff members. "
United States
Maydelin
WorldQuest Orlando Resort

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
Davenport
9.2 out of 10, Wonderful, (525 reviews)
"It was lovely! We would stay here again for sure! "
United States
Hilary
The price is AU$227
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.4 out of 10, Exceptional, (31 reviews)
"Our experience at this condo was excellent. The room was spotless and comfortable, and the space felt very safe and quiet. Parking was easy, and grocery stores and dining options were close by which made our trip convenient. The balcony view was a nice touch for morning coffee, and the AC kept the unit perfectly cool during our stay. Overall, a great location especially for Disney travelers. Highly recommend!"
United States
Kristy
The price is AU$198
includes taxes & fees
3 Feb - 4 Feb
Sunset Bliss Retreat Condo - Near Disney

Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (54 reviews)
"The place was surprisingly spacious and super clean.The area is very nice and quiet."
United States
Awilda A.
The price is AU$188
includes taxes & fees
1 Feb - 2 Feb
Private guest studio in the heart of orlando.

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,075 reviews)
"Always enjoy our stay here!"
United States
David
The price is AU$260
includes taxes & fees
1 Feb - 2 Feb
The Berkley, Orlando

Beautiful Studio near Int. Drive, Disney & Airport.

Beautiful Studio near Int. Drive, Disney & Airport.
Conway
9.2 out of 10, Wonderful, (17 reviews)
"The property is minimal but enhouses everything we needed. Great place to stay. "
United States
JoAnn E.
The price is AU$227
includes taxes & fees
4 Feb - 5 Feb
Beautiful Studio near Int. Drive, Disney & Airport.

Downtown Private Efficiency Lake Eola Central Business District

Downtown Private Efficiency Lake Eola Central Business District
Downtown Orlando
9.4 out of 10, Exceptional, (49 reviews)
"Great location has everything you need for a short stay! "
United States
MEAGAN
The price is AU$212
includes taxes & fees
4 Feb - 5 Feb
Downtown Private Efficiency Lake Eola Central Business District

Sensational Water View 1 Mile to Disney Newly Renovated Superb Location

Sensational Water View 1 Mile to Disney Newly Renovated Superb Location
Orlando
9.8 out of 10, Exceptional, (206 reviews)
"We have been stayed for 3days (2 adults 2 teens) for our Disney. This is a great place to stay especially with 1 king bed and two bunk beds, 2 full bathrooms, everyone has been relaxing. Additionally, the room is very clean and with lots of amenities. We really enjoyed it. Highly recommended!"
United States
Jianing Wang
The price is AU$297
includes taxes & fees
3 Feb - 4 Feb
Sensational Water View 1 Mile to Disney Newly Renovated Superb Location

Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood
Southern Oaks
9.8 out of 10, Exceptional, (167 reviews)
"Nice room and amazing yard/pool"
United States
Kevin O.
The price is AU$274
includes taxes & fees
12 Feb - 13 Feb
Quiet Oasis in Lovely Neighborhood

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Kissimmee
9.2 out of 10, Wonderful, (152 reviews)
"Excellent accommodations."
United States
Raychelle
The price is AU$276
includes taxes & fees
1 Feb - 2 Feb
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (197 reviews)
"Comfortable and clean room, good location."
United States
Karina
The price is AU$210
includes taxes & fees
23 Feb - 24 Feb
Barefoot'n Resort Kissimmee 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.
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Top Windermere Hotel Reviews

Find out more about Windermere

Everything you need to know about Windermere 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 Windermere 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 Windermere holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windermere holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windermere. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windermere 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 Windermere holiday rentals we have selected for you start as low as AU$128 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windermere rentals

At Expedia, we put the best Windermere 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 Windermere 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 Windermere 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 Windermere. 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 holiday rentals in Windermere?

Yes, we have holiday rentals where you'll be only 4.1 mi (6.6 km) from Universal Studios Florida, offering you a more secluded option if you'd like a quiet spot to stay. Windermere is known for its restaurants and shopping. Make sure you have time to check out the beaches and sporting events during your trip.

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

The Berkley, Orlando: This holiday home rental outside of Windermere 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 Windermere?

Expedia has 4 holiday rentals for your stay in Windermere.

What’s there to see and do in Windermere?

Lake Butler and Tibet Butler Preserve are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find popular places such as Universal Studios Florida and Universal Orlando Resort.

What’s a holiday rental in Windermere like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windermere. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.