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
The price is CA $225
CA $782 total
includes taxes & fees
Feb 10 - Feb 11
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
The price is CA $148
CA $448 total
includes taxes & fees
Feb 10 - Feb 11
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
The price is CA $248
CA $874 total
includes taxes & fees
Feb 10 - Feb 11
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
The price is CA $97
CA $141 total
includes taxes & fees
Feb 10 - Feb 11
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
The price is CA $142
CA $160 total
includes taxes & fees
Feb 22 - Feb 23
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
The price is CA $89
CA $117 total
includes taxes & fees
Mar 11 - Mar 12
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
The price is CA $112
CA $161 total
includes taxes & fees
Feb 23 - Feb 24
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
The price is CA $117
CA $132 total
includes taxes & fees
Feb 10 - Feb 11
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
The price is CA $142
CA $400 total
includes taxes & fees
Feb 10 - Feb 11
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
The price is CA $171
CA $216 total
includes taxes & fees
Feb 10 - Feb 11
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.
The price is CA $92
CA $216 total
includes taxes & fees
Feb 10 - Feb 11
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.
The price is CA $116
CA $250 total
includes taxes & fees
Feb 10 - Feb 11
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
The price is CA $117
CA $151 total
includes taxes & fees
Feb 10 - Feb 11
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
The price is CA $103
CA $232 total
includes taxes & fees
Feb 10 - Feb 11
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.
The price is CA $111
CA $213 total
includes taxes & fees
Mar 11 - Mar 12
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
The price is CA $144
CA $181 total
includes taxes & fees
Mar 1 - Mar 2
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
The price is CA $75
CA $186 total
includes taxes & fees
Feb 11 - Feb 12
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.
The price is CA $165
CA $379 total
includes taxes & fees
Feb 11 - Feb 12
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.
The price is CA $82
CA $156 total
includes taxes & fees
Feb 27 - Feb 28
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.
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windermere. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.