Windermere Vacation Rentals

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Our top choices for Windermere vacation rentals

Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is CA $168
CA $783 total
includes taxes & fees
Apr 17 - Apr 18
Rustic Hideaway - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is CA $149
CA $699 total
includes taxes & fees
Apr 20 - Apr 21
The Farm House - Great Location + Pet Friendly!

Upstay 2BR Family Condo Ventura Golf Country Club

Upstay 2BR Family Condo Ventura Golf Country Club
2.0 star property
Ventura
The price is CA $119
CA $360 total
includes taxes & fees
Apr 19 - Apr 20
Upstay 2BR Family Condo Ventura Golf Country Club

Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is CA $120
CA $230 total
includes taxes & fees
Apr 19 - Apr 20
Cozy Modern Studio

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, (1,873 reviews)
"Breakfast was great and staff were pleasant. "
United States
Debra
The price is CA $88
CA $99 total
includes taxes & fees
May 3 - May 4
The View Studio Suites and Event Venue

~ 2 Mi to Disney & Universal: Orlando Resort Condo

~ 2 Mi to Disney & Universal: Orlando Resort Condo
3.5 star property
Orlando
~ 2 Mi to Disney & Universal: Orlando Resort Condo

Bright 3BR Resort Condo Near Disney + Pools

Bright 3BR Resort Condo Near Disney + Pools
3.0 star property
Davenport
The price is CA $119
CA $484 total
includes taxes & fees
Apr 20 - Apr 21
Bright 3BR Resort Condo Near Disney + Pools

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.2 out of 10, Wonderful, (267 reviews)
"We love staying at this resort, great area"
United States
Mary
The price is CA $167
CA $206 total
includes taxes & fees
Apr 17 - Apr 18
Barefoot'n Resort Kissimmee Orlando

Marriott's Grande Vista

Marriott's Grande Vista
4.0 star property
Orlando
9.0 out of 10, Wonderful, (4,172 reviews)
"Great place to stay"
United States
Candise
The price is CA $191
CA $215 total
includes taxes & fees
Apr 26 - Apr 27
Marriott's Grande Vista

Floridays Resort Orlando

Floridays Resort Orlando
3.5 star property
International Drive District
8.6 out of 10, Excellent, (11,840 reviews)
"Everything was really nice!"
United States
Tanisha
The price is CA $175
CA $251 total
includes taxes & fees
Apr 21 - Apr 22
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, (3,106 reviews)
"Great location and amenities."
United States
Jennifer
The price is CA $129
CA $417 total
includes taxes & fees
May 11 - May 12
Regal Oaks Resort Vacation Townhomes by IDILIQ

Vacational Apartment at Orlando 3608

Vacational Apartment at Orlando 3608
2.0 star property
Ventura
The price is CA $159
CA $268 total
includes taxes & fees
May 5 - May 6
Vacational Apartment at Orlando 3608

Luxury House - Sleeps 8 Golf Disney Family Fun

Luxury House - Sleeps 8 Golf Disney Family Fun
2.0 star property
Ventura
The price is CA $264
CA $800 total
includes taxes & fees
Apr 30 - May 1
Luxury House - Sleeps 8 Golf Disney Family Fun

Apartment 1 BR Free Shuttle to Disney Parks

Apartment 1 BR Free Shuttle to Disney Parks
3.5 star property
Orlando
The price is CA $121
CA $368 total
includes taxes & fees
May 12 - May 13
Apartment 1 BR Free Shuttle to Disney Parks

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,877 reviews)
"Nice place to stay and close to the parks. "
United States
Kena
The price is CA $99
CA $147 total
includes taxes & fees
Apr 19 - Apr 20
Vacation Village Orlando, Celebration

Poolside Bliss & Theme Park Thrills: Orlando Oasis

Poolside Bliss & Theme Park Thrills: Orlando Oasis
3.5 star property
International Drive District
The price is CA $110
CA $539 total
includes taxes & fees
Apr 21 - Apr 22
Poolside Bliss & Theme Park Thrills: Orlando Oasis

The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.4 out of 10, Very good, (988 reviews)
"Really nice place to stay and nice location "
United States
Alfredo
The price is CA $84
CA $112 total
includes taxes & fees
May 4 - May 5
The Point Hotel & Suites Orlando

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
4.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Room was clean and ammenities were as advertised. "
United States
John
The price is CA $129
CA $330 total
includes taxes & fees
Apr 21 - Apr 22
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
4.0 star property
International Drive District
9.2 out of 10, Wonderful, (3,295 reviews)
"Excellent stay"
United States
TEISHA
The price is CA $172
CA $193 total
includes taxes & fees
May 11 - May 12
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens

Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens
4.0 star property
International Drive District
The price is CA $193
CA $684 total
includes taxes & fees
Apr 28 - Apr 29
Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens
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 3 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.