Windermere Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Windermere vacation rentals

Front of property

Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
$553 nightly
The price is $614
Mar 29 - Mar 30
Total with taxes and fees
Rustic Hideaway - Great Location + Pet Friendly!
Exterior

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.6 out of 10, Good, (1,001 reviews)
"My family and I had an amazing stay, staff were amazing and friendly, cleans rooms and very well located. "
United States
Alexandro
$91 nightly
The price is $103
Apr 13 - Apr 14
Total with taxes and fees
voco Kissimmee Orlando by IHG
Beach

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
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 31 - Apr 1
Total with taxes and fees
Tiny Hidden Cottage
Terrace/patio

The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
9.0 out of 10, Wonderful, (23 reviews)
"The host communicated when needed. A great stay for a quick trip. "
United States
Jamee O.
$134 nightly
The price is $148
Mar 30 - Mar 31
Total with taxes and fees
The Cozy Crash Pad: Tiny House Experience
1 bedroom, iron/ironing board, WiFi, bed sheets

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Southchase
9.8 out of 10, Exceptional, (24 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 30 - Mar 31
Total with taxes and fees
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Outdoor pool

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, (26 reviews)
"Clean and neat accommodations. "
United States
Kay D.
$99 nightly
The price is $108
Mar 29 - Mar 30
Total with taxes and fees
Private Spacious Room in Home, with Pool-The Oasis Room
Interior

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (21 reviews)
"This place was very nice. The bed was comfortable. We had great view of the lake. It was very peaceful. Also, the hosts were very responsive."
United States
Elaine H.
$261 nightly
The price is $287
Mar 27 - Mar 28
Total with taxes and fees
Cozy Lake Front Cottage
Interior

Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood
Southern Oaks
9.8 out of 10, Exceptional, (173 reviews)
"We really enjoyed our stay. Perfect for overnight. "
United States
Regina B.
$171 nightly
The price is $190
Apr 1 - Apr 2
Total with taxes and fees
Quiet Oasis in Lovely Neighborhood
Dining

Private house with pool Kissimmee/Orlando

Private house with pool Kissimmee/Orlando
Buena Ventura Lakes
9.8 out of 10, Exceptional, (55 reviews)
"Great location and close to Silver Spurs arena. Host was very responsive "
United States
Brandy C.
$383 nightly
The price is $428
Mar 31 - Apr 1
Total with taxes and fees
Private house with pool Kissimmee/Orlando
Interior

Cozy studio in fabulous Orlando close to everything

Cozy studio in fabulous Orlando close to everything
Orlando
9.8 out of 10, Exceptional, (15 reviews)
"The host is wonderful and the place was exactly what I needed. The bed was extremely comfortable and the neighborhood really quiet. I will definitely be back and stay here again."
United States
Robin L.
$150 nightly
The price is $166
Mar 29 - Mar 30
Total with taxes and fees
Cozy studio in fabulous Orlando close to everything
1 bedroom, desk, iron/ironing board, free WiFi

Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (57 reviews)
"The guest studio was really good; good facilities, clean and tidy and with lovely little touches in the bathroom. "
United Kingdom
Rebecca
$129 nightly
The price is $143
Apr 20 - Apr 21
Total with taxes and fees
Private guest studio in the heart of orlando.
Exterior

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (97 reviews)
"Pet amenities are great. Food bowls, toys, etc. Beds and pillows super comfortable. Host is fabulously helpful. "
United States
Fran G.
$294 nightly
The price is $328
Apr 8 - Apr 9
Total with taxes and fees
Eastpark. Pet friendly! Lake Nona
1 bedroom, iron/ironing board, free WiFi, bed sheets

Beautiful Studio near Int. Drive, Disney & Airport.

Beautiful Studio near Int. Drive, Disney & Airport.
Conway
9.2 out of 10, Wonderful, (19 reviews)
"Great communication and made the spacing super comfortable. Cleanness and quick on responses! Love"
United States
Jadaiya W.
$143 nightly
The price is $158
Mar 29 - Mar 30
Total with taxes and fees
Beautiful Studio near Int. Drive, Disney & Airport.
Exterior

Charming 2-bedroom apartment in house with AC, WiFi included

Charming 2-bedroom apartment in house with AC, WiFi included
Apopka
9.8 out of 10, Exceptional, (24 reviews)
"It was quiet, clean and had snacks and drinks for us."
United States
Lori
$139 nightly
The price is $153
Mar 29 - Mar 30
Total with taxes and fees
Charming 2-bedroom apartment in house with AC, WiFi included
Smart TV, table tennis

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Azalea Park
9.6 out of 10, Exceptional, (20 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 29 - Mar 30
Total with taxes and fees
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Smart TV, DVD player

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
9.8 out of 10, Exceptional, (35 reviews)
"Lovely spot, in a quiet neighborhood. Clean and spotless, and stocked with amenities for breakfast and snacks. We'll be booking again next time we go down to visit family in Orlando."
United States
John
$284 nightly
The price is $317
Apr 2 - Apr 3
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Private kitchen

Charming 2-bedroom Florida Getaway! Sleeps 6

Charming 2-bedroom Florida Getaway! Sleeps 6
Kissimmee
10.0 out of 10, Exceptional, (9 reviews)
$279 nightly
The price is $313
Apr 20 - Apr 21
Total with taxes and fees
Charming 2-bedroom Florida Getaway! Sleeps 6
Property grounds

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (33 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
$384 nightly
The price is $425
Apr 5 - Apr 6
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
Restaurant

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, (1,814 reviews)
"Clean room, GREAT breakfast, great service, and great price. "
United States
Anonymous traveler
$95 nightly
The price is $107
Mar 29 - Mar 30
Total with taxes and fees
The View Studio Suites and Event Venue
Front of property

Premium Condos near Universal Studios

Premium Condos near Universal Studios
3.5 star property
International Drive District
9.4 out of 10, Exceptional, (34 reviews)
"Awesome place. "
United States
Ryan
$147 nightly
The price is $166
Mar 31 - Apr 1
Total with taxes and fees
Premium Condos near Universal Studios
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"This was our third stay, and we had a wonderful time! The room was spacious and clean, food at the resort was good, and staff was incredibly hospitable and welcoming. We will be back again!"
Cassandra 6-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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 $96 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.