Windermere Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

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 ￥21,827
￥55,231 total
includes taxes & fees
Mar 1 - Mar 2
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Interior

The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ￥23,269
￥86,464 total
includes taxes & fees
Feb 27 - Feb 28
The Farm House - Great Location + Pet Friendly!
Front of property

Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ￥29,823
￥101,453 total
includes taxes & fees
Mar 1 - Mar 2
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, (1,000 reviews)
"Staff was very helpful, location was what we needed and rooms and pool were outstanding "
United States
Chester Joseph
The price is ￥9,854
￥14,723 total
includes taxes & fees
Mar 2 - Mar 3
voco Kissimmee Orlando by IHG
Terrace/patio

The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
9.0 out of 10, Wonderful, (22 reviews)
"The host communicated when needed. A great stay for a quick trip. "
United States
Jamee O.
The price is ￥9,978
￥23,113 total
includes taxes & fees
Mar 9 - Mar 10
The Cozy Crash Pad: Tiny House Experience
Exterior

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,473 reviews)
"Yes .. very clean rooms and hotel chef was great"
United States
Alicia
The price is ￥12,503
￥18,090 total
includes taxes & fees
Mar 24 - Mar 25
Vacation Village Orlando, Celebration
Exterior detail

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 ￥13,272
￥28,594 total
includes taxes & fees
Mar 4 - Mar 5
Cozy Private Apartment - Stylish & Spotless — No sharing areas
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, (22 reviews)
"Quiet peaceful location"
United States
joseph B.
The price is ￥11,226
￥20,133 total
includes taxes & fees
Mar 1 - Mar 2
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Beach

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.2 out of 10, Wonderful, (62 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.
The price is ￥12,317
￥23,898 total
includes taxes & fees
Mar 29 - Mar 30
Tiny Hidden Cottage
Marina

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 ￥13,096
￥27,985 total
includes taxes & fees
Mar 23 - Mar 24
NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
Pool

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (22 reviews)
"Great location , Very enjoy , private space, would book in the future for sure "
United States
Matt B.
The price is ￥17,150
￥42,018 total
includes taxes & fees
Mar 8 - Mar 9
Spacious & Private Guest Pool House Oasis
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, (24 reviews)
"This was a perfect small space for two people Gorgeous pool, and great communication with the host. "
United States
Daniella D.
The price is ￥8,419
￥16,790 total
includes taxes & fees
Mar 7 - Mar 8
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, (20 reviews)
"Will definitely be staying again"
United States
Tom W.
The price is ￥19,477
￥42,698 total
includes taxes & fees
Feb 27 - Feb 28
Cozy Lake Front Cottage
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
10.0 out of 10, Exceptional, (9 reviews)
"Great host, and stayed connected with us."
United States
Christopher
The price is ￥16,371
￥39,076 total
includes taxes & fees
Mar 1 - Mar 2
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Property grounds

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (31 reviews)
"One of our best stays. "
United States
matthew m.
The price is ￥23,714
￥56,402 total
includes taxes & fees
Mar 8 - Mar 9
Incredible Private Lakefront Cottage Retreat
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, (18 reviews)
"It was quiet, clean and had snacks and drinks for us."
United States
Lori
The price is ￥16,137
￥23,027 total
includes taxes & fees
Feb 27 - Feb 28
Charming 2-bedroom apartment in house with AC, WiFi included
Interior

Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood
Southern Oaks
9.8 out of 10, Exceptional, (170 reviews)
"Quiet, private space with comfortable accommodations and excellent amenities."
United States
Tre N.
The price is ￥14,032
￥31,182 total
includes taxes & fees
Feb 28 - Mar 1
Quiet Oasis in Lovely Neighborhood
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)
"The property is minimal but enhouses everything we needed. Great place to stay. "
United States
JoAnn E.
The price is ￥10,524
￥24,604 total
includes taxes & fees
Mar 2 - Mar 3
Beautiful Studio near Int. Drive, Disney & Airport.
Dining

Private house with pool Kissimmee/Orlando

Private house with pool Kissimmee/Orlando
Buena Ventura Lakes
9.8 out of 10, Exceptional, (53 reviews)
"The house was clean. We loved the overall design and how spacious it was. The pool was perfect for our children. Everything was perfect for our stay."
United States
Queinton C.
The price is ￥26,544
￥63,893 total
includes taxes & fees
Mar 12 - Mar 13
Private house with pool Kissimmee/Orlando
Exterior

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (96 reviews)
"Nice place!"
United States
Anonymous traveler
The price is ￥22,607
￥51,100 total
includes taxes & fees
Mar 16 - Mar 17
Eastpark. Pet friendly! Lake Nona
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

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"Good room, good food choices, fun play area for the children "
Tamara 1-night trip
Posted 10 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG

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: 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.