Windermere Vacation Rentals

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Our top choices for Windermere vacation rentals

The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
$517 nightly
The price is $574
Feb 10 - Feb 11
Total with taxes and fees
The Farm House - Great Location + Pet Friendly!

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
$290 nightly
The price is $322
Feb 10 - Feb 11
Total with taxes and fees
Shore Steps Cottage - Walking Distance To The Town Of Windermere

Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
$577 nightly
The price is $642
Feb 10 - Feb 11
Total with taxes and fees
Rustic Hideaway - Great Location + Pet Friendly!

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.6 out of 10, Good, (1,014 reviews)
"Staff was very helpful, location was what we needed and rooms and pool were outstanding "
United States
Chester Joseph
$91 nightly
The price is $103
Feb 10 - Feb 11
Total with taxes and fees
voco Kissimmee Orlando by IHG

Fairfield Inn & Suites Orlando Int'l Drive/Convention Center

Fairfield Inn & Suites Orlando Int'l Drive/Convention Center
2.5 star property
International Drive District
8.6 out of 10, Excellent, (1,005 reviews)
"Excelent location, clean room and the staff is great"
United States
Maite
$99 nightly
The price is $111
Feb 25 - Feb 26
Total with taxes and fees
Fairfield Inn & Suites Orlando Int'l Drive/Convention Center

The Point by Edge

The Point by Edge
4.0 star property
Florida Center
8.4 out of 10, Very Good, (878 reviews)
"Great view, pleasant staff."
United States
Crystal
$83 nightly
The price is $93
Mar 11 - Mar 12
Total with taxes and fees
The Point by Edge

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,310 reviews)
"Yes .. very clean rooms and hotel chef was great"
United States
Alicia
$117 nightly
The price is $132
Feb 24 - Feb 25
Total with taxes and fees
Vacation Village Orlando, Celebration

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, (1,619 reviews)
"Clean and spacious rooms and the breakfast was great."
United States
Karen
$95 nightly
The price is $107
Feb 10 - Feb 11
Total with taxes and fees
The View Studio Suites and Event Venue

Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis

Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis
4.5 star property
Lindfields
$279 nightly
The price is $292
Feb 10 - Feb 11
Total with taxes and fees
Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis

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, (528 reviews)
"It was lovely! We would stay here again for sure! "
United States
Hilary
$141 nightly
The price is $158
Feb 10 - Feb 11
Total with taxes and fees
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Beautiful Studio near Int. Drive, Disney & Airport.

Beautiful Studio near Int. Drive, Disney & Airport.
Conway
9.4 out of 10, Exceptional, (18 reviews)
"The property is minimal but enhouses everything we needed. Great place to stay. "
United States
JoAnn E.
$143 nightly
The price is $158
Feb 10 - Feb 11
Total with taxes and fees
Beautiful Studio near Int. Drive, Disney & Airport.

Cozy Private Apartment - Stylish & Spotless — No sharing areas

Cozy Private Apartment - Stylish & Spotless — No sharing areas
Orlando
10.0 out of 10, Exceptional, (29 reviews)
"Mercedes is an amazing host and has thought of - and provided EVERYTHING you need for a fantastic stay. Would ABSOLUTELY stay here again and HIGHLY recommend!!"
United States
Rick K.
$165 nightly
The price is $183
Feb 10 - Feb 11
Total with taxes and fees
Cozy Private Apartment - Stylish & Spotless — No sharing areas

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,823 reviews)
"Great place. To stay "
United States
THOMAS
$97 nightly
The price is $110
Feb 10 - Feb 11
Total with taxes and fees
Barefoot Suites

NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry

NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
Orlando
9.2 out of 10, Wonderful, (13 reviews)
"I stayed at the property from Oct 31st to Nov 2nd for the weekend. This is a very cozy and clean studio apartment which was perfect fo myself and my 2 dogs. There is a fenced in yard at lights at night so my dogs really enjoyed it also. "
United States
michael
$160 nightly
The price is $169
Feb 10 - Feb 11
Total with taxes and fees
NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.2 out of 10, Wonderful, (62 reviews)
"It was a good area to stay "
United States
Christanah O.
$133 nightly
The price is $146
Mar 11 - Mar 12
Total with taxes and fees
Tiny Hidden Cottage

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (202 reviews)
"Great place. Great location. "
United States
Andrew
$115 nightly
The price is $131
Feb 26 - Feb 27
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando

Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.4 out of 10, Exceptional, (32 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
$122 nightly
The price is $136
Feb 11 - Feb 12
Total with taxes and fees
Sunset Bliss Retreat Condo - Near Disney

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (19 reviews)
"Will definitely be staying again"
United States
Tom W.
$250 nightly
The price is $274
Feb 11 - Feb 12
Total with taxes and fees
Cozy Lake Front Cottage

Private Spacious Room in Home, with Pool-The Oasis Room

Private Spacious Room in Home, with Pool-The Oasis Room
Clermont
9.6 out of 10, Exceptional, (24 reviews)
"Great host great property"
United States
Ken K.
$105 nightly
The price is $114
Feb 27 - Feb 28
Total with taxes and fees
Private Spacious Room in Home, with Pool-The Oasis Room

Boulder Ridge Villas at Disney's Wilderness Lodge

Boulder Ridge Villas at Disney's Wilderness Lodge
4.0 star property
Bay Lake
8.8 out of 10, Excellent, (54 reviews)
"Looking for perfect compliment to your ultimate Disney World experience? Look no further than the Wilderness Lodge Villas. Not only are the rooms cozy and comfortable but the rustic atmosphere is spot on. After a long day at the Magic Kingdom, there is no better experience than taking the boat back to the lodge, especially at night. You can either recharge your batteries and go back, or you can enjoy all the amenities and atmosphere of the lodge. The only negative was that the food selection at...
United States
David O.
$466 nightly
The price is $525
Feb 22 - Feb 23
Total with taxes and fees
Boulder Ridge Villas at Disney's Wilderness Lodge
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 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 Windermere 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 Windermere vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windermere vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windermere 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 $93 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 Windermere rentals

At Expedia, we put the best Windermere 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 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 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 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 vacation rentals in Windermere?

Yes, we offer vacation rentals where you'll be only 4.1 mi (6.6 km) from Universal Studios Florida, offering you a 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's the top vacation rental that Windermere has to offer?

The Berkley, Orlando: Visitors like this Windermere vacation home rental. It 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 Windermere?

Expedia has 4 vacation 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 larger area, you’ll find popular places like Universal Studios Florida and Universal Orlando Resort.

What’s a vacation rental in Windermere like?

Vacation rentals are private properties you can book for several days or longer in Windermere. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family getaway.