Windermere Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Windermere vacation rentals

Interior

Villa in Windermere

The Farm House - Great Location + Pet Friendly!
3.0 star property
$507 nightly
The price is $563
Mar 18 - Mar 19
Total with taxes and fees
The Farm House - Great Location + Pet Friendly!
Front of property

Villa in Windermere

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
$568 nightly
The price is $632
Mar 18 - Mar 19
Total with taxes and fees
Rustic Hideaway - Great Location + Pet Friendly!
Exterior

Aparthotel in Kissimmee

voco Kissimmee Orlando by IHG
4.0 star property
7.6 out of 10, Good, (1,001 reviews)
"excellent stay !"
United States
Haley
$90 nightly
The price is $102
Mar 16 - Mar 17
Total with taxes and fees
voco Kissimmee Orlando by IHG
2 bedrooms, iron/ironing board, WiFi, bed sheets

Apartment in Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
10.0 out of 10, Exceptional, (10 reviews)
"Great host, and stayed connected with us."
United States
Christopher
$225 nightly
The price is $251
Mar 13 - Mar 14
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Beach

Cottage in Longwood

Tiny Hidden Cottage
9.4 out of 10, Exceptional, (63 reviews)
"Great little cottage, it was easy to locate and access the property. Nice quiet area and we really enjoyed our stay."
United States
Anna M.
$131 nightly
The price is $144
Mar 17 - Mar 18
Total with taxes and fees
Tiny Hidden Cottage
Marina

Apartment in Orlando

NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
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
$162 nightly
The price is $172
Mar 30 - Mar 31
Total with taxes and fees
NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
1 bedroom, iron/ironing board, WiFi, bed sheets

Apartment in Southchase

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
9.8 out of 10, Exceptional, (22 reviews)
"Everything was amazing described how it was owners were super sweet and loving we were happy to find this place to stay "
United States
Pamela Y.
$117 nightly
The price is $129
Mar 14 - Mar 15
Total with taxes and fees
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Terrace/patio

Vacation Home in Orlando

The Cozy Crash Pad: Tiny House Experience
9.0 out of 10, Wonderful, (22 reviews)
"The host communicated when needed. A great stay for a quick trip. "
United States
Jamee O.
$134 nightly
The price is $148
Mar 16 - Mar 17
Total with taxes and fees
The Cozy Crash Pad: Tiny House Experience
1 bedroom, desk, iron/ironing board, free WiFi

Apartment in Orlando

Private guest studio in the heart of orlando.
9.8 out of 10, Exceptional, (57 reviews)
"The place was surprisingly spacious and super clean.The area is very nice and quiet."
United States
Awilda A.
$122 nightly
The price is $134
Mar 16 - Mar 17
Total with taxes and fees
Private guest studio in the heart of orlando.
Exterior detail

Apartment in Orlando

Cozy Private Apartment - Stylish & Spotless — No sharing areas
10.0 out of 10, Exceptional, (30 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
Apr 1 - Apr 2
Total with taxes and fees
Cozy Private Apartment - Stylish & Spotless — No sharing areas
Exterior

Vacation Home in East Park

Eastpark. Pet friendly! Lake Nona
9.2 out of 10, Wonderful, (96 reviews)
"Pet amenities are great. Food bowls, toys, etc. Beds and pillows super comfortable. Host is fabulously helpful. "
United States
Fran G.
$307 nightly
The price is $341
Mar 16 - Mar 17
Total with taxes and fees
Eastpark. Pet friendly! Lake Nona
Interior

Aparthotel in Southern Oaks

Quiet Oasis in Lovely Neighborhood
9.8 out of 10, Exceptional, (170 reviews)
"We really enjoyed our stay. Perfect for overnight. "
United States
Regina B.
$171 nightly
The price is $190
Mar 17 - Mar 18
Total with taxes and fees
Quiet Oasis in Lovely Neighborhood
4 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)

Condo resort in Orlando

Marriott's Grande Vista
4.0 star property
9.0 out of 10, Wonderful, (4,010 reviews)
"Very nice clean hotel. Family resort style. "
United States
Desha-Nay
$111 nightly
The price is $125
Apr 11 - Apr 12
Total with taxes and fees
Marriott's Grande Vista
Interior

Cottage in Clermont

Cozy Lake Front Cottage
10.0 out of 10, Exceptional, (21 reviews)
"Will definitely be staying again"
United States
Tom W.
$258 nightly
The price is $284
Mar 15 - Mar 16
Total with taxes and fees
Cozy Lake Front Cottage
Outdoor pool

Vacation Home in Clermont

Private Spacious Room in Home, with Pool-The Oasis Room
9.6 out of 10, Exceptional, (24 reviews)
"This was a perfect small space for two people Gorgeous pool, and great communication with the host. "
United States
Daniella D.
$105 nightly
The price is $114
Mar 29 - Mar 30
Total with taxes and fees
Private Spacious Room in Home, with Pool-The Oasis Room
Exterior

Vacation Home in Apopka

Charming 2-bedroom apartment in house with AC, WiFi included
9.6 out of 10, Exceptional, (20 reviews)
"It was quiet, clean and had snacks and drinks for us."
United States
Lori
$134 nightly
The price is $148
Mar 15 - Mar 16
Total with taxes and fees
Charming 2-bedroom apartment in house with AC, WiFi included
Front of property

Condo resort in International Drive District

Premium Condos near Universal Studios
3.5 star property
9.4 out of 10, Exceptional, (34 reviews)
"Awesome place. "
United States
Ryan
$145 nightly
The price is $164
Mar 31 - Apr 1
Total with taxes and fees
Premium Condos near Universal Studios
1 bedroom, iron/ironing board, free WiFi, bed sheets

Apartment in Conway

Beautiful Studio near Int. Drive, Disney & Airport.
9.2 out of 10, Wonderful, (19 reviews)
"The property is minimal but enhouses everything we needed. Great place to stay. "
United States
JoAnn E.
$143 nightly
The price is $158
Mar 17 - Mar 18
Total with taxes and fees
Beautiful Studio near Int. Drive, Disney & Airport.
Property grounds

Cottage in Altamonte Springs

Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (31 reviews)
"The host was great! Love the lake and building a fire!"
United States
Rebekah W.
$377 nightly
The price is $417
Apr 1 - Apr 2
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
Smart TV, table tennis

Vacation Home in Azalea Park

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
9.6 out of 10, Exceptional, (19 reviews)
"Place was clean and had plenty of space for us. Check-in was easy and the host is very responsive and helpful."
United States
Ryan V.
$243 nightly
The price is $270
Mar 15 - Mar 16
Total with taxes and fees
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
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.
View all properties

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windermere Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Incredible hotel! I will be back!"
William 1-night trip
Posted 2 hours ago
Universal's Cabana Bay Beach Resort

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.

Explore a world of travel with Expedia

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.