Windermere Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Windermere vacation rentals

Property grounds

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
The price is ￥21,355
￥56,632 total
includes taxes & fees
Jun 2 - Jun 3
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Villa (5 Bedrooms) | Interior

Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ￥23,244
￥94,340 total
includes taxes & fees
Jun 1 - Jun 2
Rustic Hideaway - Great Location + Pet Friendly!
Villa (3 Bedrooms) | Interior

The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ￥22,961
￥87,409 total
includes taxes & fees
Jun 1 - Jun 2
The Farm House - Great Location + Pet Friendly!
Exterior

Hilton Vacation Club Grand Beach Orlando

Hilton Vacation Club Grand Beach Orlando
3.0 star property
Orlando
9.4 out of 10, Exceptional, (1,522 reviews)
"Great resort!!"
United States
Nathaniel
The price is ￥15,925
￥22,396 total
includes taxes & fees
Jun 7 - Jun 8
Hilton Vacation Club Grand Beach Orlando
Exterior

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,232 reviews)
"Great great stay currently my go to place to stay when I’m in town"
United States
Mario
The price is ￥10,320
￥15,693 total
includes taxes & fees
Jun 2 - Jun 3
Vacation Village Orlando, Celebration
Exterior

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (99 reviews)
"Very nice accommodations. Great stay!!"
United States
John G.
The price is ￥15,766
￥44,590 total
includes taxes & fees
Jun 1 - Jun 2
Eastpark. Pet friendly! Lake Nona
Outdoor pool

Aster Cove

Aster Cove
4.0 star property
Crescent Lakes
The price is ￥24,048
￥86,501 total
includes taxes & fees
Jun 1 - Jun 2
Aster Cove
3 bedrooms, desk, iron/ironing board, free WiFi

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (49 reviews)
"The house was very clean and the owner was very prompt in answering our one question. The A/C worked great. "
United States
Michael
The price is ￥20,782
￥39,425 total
includes taxes & fees
Jun 8 - Jun 9
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
1 bedroom, iron/ironing board, free 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, (29 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.
The price is ￥11,466
￥21,459 total
includes taxes & fees
Jun 2 - Jun 3
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Apartment, Patio

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
The price is ￥15,167
￥67,824 total
includes taxes & fees
Jun 7 - Jun 8
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
Property grounds

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (36 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.
The price is ￥24,047
￥59,897 total
includes taxes & fees
May 31 - Jun 1
Incredible Private Lakefront Cottage Retreat
Fridge, microwave, oven, stovetop

Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (109 reviews)
"We enjoyed a great stay! "
United States
Amanda B.
The price is ￥23,888
￥54,843 total
includes taxes & fees
May 31 - Jun 1
Stylish Boutique Guest house in Winter Park
Interior

Cozy studio in fabulous Orlando close to everything

Cozy studio in fabulous Orlando close to everything
Orlando
9.8 out of 10, Exceptional, (19 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.
The price is ￥15,925
￥26,475 total
includes taxes & fees
May 30 - May 31
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, (58 reviews)
"Super clean and updated, loved the location, and quiet neighborhood. Definitely will stay here again!"
United States
Gianna N.
The price is ￥11,195
￥22,051 total
includes taxes & fees
Jun 1 - Jun 2
Private guest studio in the heart of orlando.
Interior entrance

Family Friendly Davenport Pool Villa

Family Friendly Davenport Pool Villa
4.0 star property
Florida Pines
The price is ￥23,238
￥84,404 total
includes taxes & fees
May 31 - Jun 1
Family Friendly Davenport Pool Villa
2 bedrooms, iron/ironing board, WiFi, bed sheets

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.8 out of 10, Exceptional, (12 reviews)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
The price is ￥16,721
￥41,027 total
includes taxes & fees
May 31 - Jun 1
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
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, (30 reviews)
"Very nice neighborhood and great accommodations. "
United States
Kevin S.
The price is ￥15,766
￥23,609 total
includes taxes & fees
May 30 - May 31
Charming 2-bedroom apartment in house with AC, WiFi included
Interior

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (22 reviews)
"Host was very accommodating and the cottage was perfect"
United States
Ashley P.
The price is ￥21,355
￥46,158 total
includes taxes & fees
May 31 - Jun 1
Cozy Lake Front Cottage
1 bedroom, iron/ironing board, free WiFi, bed sheets

Beautiful Studio near Int. Drive, Disney & Airport.

Beautiful Studio near Int. Drive, Disney & Airport.
Conway
9.4 out of 10, Exceptional, (23 reviews)
"A very clean property and close to the Hilton where my conference was 10 out of 10 recommend because those other attendees that stayed at the Hilton had a very horrible experience and I was blessed to be staying at this clean private suite."
United States
Diana
The price is ￥8,600
￥22,714 total
includes taxes & fees
Jun 2 - Jun 3
Beautiful Studio near Int. Drive, Disney & Airport.
Exterior

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Kissimmee
9.2 out of 10, Wonderful, (167 reviews)
"Not far from Disney properties. Great amenities!"
United States
DELMA T.
The price is ￥10,351
￥33,009 total
includes taxes & fees
Jun 1 - Jun 2
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"We didn’t spend much time at the hotel but the time we did it was great. Had everything you need. Pools were great and lazy river was cool with view of Volcano Bay. Cool retro style. Budget friendly though it doesn’t feel like it’s a budget hotel. Buses to the parks were easy to catch and quick. I don’t have a single complaint."
Errik 2-night trip
Posted less than an hour ago
Universal's Cabana Bay Beach Resort

Find out more about Windermere

Search for holiday rentals in Windermere on Expedia! You can easily find your home rentals, villas, holiday apartments in Windermere using one of the methods below:

  • View our selection of featured holiday rentals in Windermere
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  • Enter your travel dates to view the best deals on holiday rentals in Windermere while they last

Look no further and take a look at our great range of rental properties in Windermere!

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: You might want to consider this vacation home rental near Windermere, which 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. Another good choice for your trip to Windermere is Grand Luxury Lakes 3BR Townhouse near Disney.

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.