Windermere Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Windermere vacation rentals

Exterior
voco Kissimmee Orlando by IHG

Aparthotel in Kissimmee

voco Kissimmee Orlando by IHG
4.0 star property
7.6 out of 10, Good, (1003)
"Place was clean, staff great, cozy very nice area swimming pool"
United States
KRYSTLE
The price is ￥9,681
￥14,532 total
includes taxes & fees
Jan 7 - Jan 8, 2026
voco Kissimmee Orlando by IHG
Lobby sitting area
The View Studio Suites and Event Venue

Aparthotel in Orlando

The View Studio Suites and Event Venue
3.0 star property
8.4 out of 10, Very Good, (1493)
"Good sized room, nice staff, good breakfast "
United States
Catherine
The price is ￥13,333
￥15,000 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The View Studio Suites and Event Venue
Terrace/patio
The Point by Edge

Aparthotel in Florida Center

The Point by Edge
4.0 star property
8.4 out of 10, Very Good, (833)
"It was great really recommend this place"
United States
Sharam
The price is ￥8,994
￥12,052 total
includes taxes & fees
Jan 15 - Jan 16, 2026
The Point by Edge
Exterior
Barefoot'n Resort Kissimmee Orlando

Aparthotel in Kissimmee

Barefoot'n Resort Kissimmee Orlando
2.5 star property
9.0 out of 10, Wonderful, (179)
"Comfortable and clean room, good location."
United States
Karina
The price is ￥17,337
￥21,624 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Barefoot'n Resort Kissimmee Orlando
Exterior
Sunset Bliss Retreat Condo - Near Disney

Apartment in Kissimmee

Sunset Bliss Retreat Condo - Near Disney
9.4 out of 10, Exceptional, (28)
"Amazing spot and location was great!"
United States
Alfred
The price is ￥7,360
￥19,790 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Sunset Bliss Retreat Condo - Near Disney
Smart TV
Thornton park oasis 1 bedroom

Apartment in Thornton Park

Thornton park oasis 1 bedroom
2.0 star property
10.0 out of 10, Exceptional, (12)
"very comfortable stay in a lovely neighborhood!"
United States
Polly c.
The price is ￥10,618
￥23,851 total
includes taxes & fees
Dec 28 - Dec 29
Thornton park oasis 1 bedroom
Interior
Tiny Hidden Cottage

Cottage in Longwood

Tiny Hidden Cottage
9.2 out of 10, Wonderful, (59)
"Check in process and house were both great. "
United States
Marc H.
The price is ￥12,335
￥23,933 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Tiny Hidden Cottage
Exterior
Cozy Private Apartment - Stylish & Spotless — No sharing areas

Apartment in Orlando

Cozy Private Apartment - Stylish & Spotless — No sharing areas
10.0 out of 10, Exceptional, (29)
"This was an excellent place to stay. Perfect for a couple. The entire place was extremely clean and very welcoming. We would absolutely stay here again. "
United States
Craig K.
The price is ￥13,255
￥28,557 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Cozy Private Apartment - Stylish & Spotless — No sharing areas
Fridge, microwave, stovetop, coffee/tea maker
Private guest studio in the heart of orlando.

Apartment in Orlando

Private guest studio in the heart of orlando.
9.8 out of 10, Exceptional, (54)
"Really cute place and has everything you need for a stay!"
United States
Emily D.
The price is ￥9,696
￥20,181 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Private guest studio in the heart of orlando.
2 outdoor pools, open 8 AM to 10 PM, sun loungers
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Aparthotel in Davenport

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
9.2 out of 10, Wonderful, (507)
"Great place"
United States
Bobby
The price is ￥19,518
￥24,657 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Pool
Quiet Oasis in Lovely Neighborhood

Aparthotel in Southern Oaks

Quiet Oasis in Lovely Neighborhood
9.8 out of 10, Exceptional, (162)
"Great place! "
United States
Alice H.
The price is ￥12,647
￥29,648 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Quiet Oasis in Lovely Neighborhood
Reception
Florida Hotel & Conference Center in the Florida Mall

Aparthotel in Orlando

Florida Hotel & Conference Center in the Florida Mall
3.5 star property
9.2 out of 10, Wonderful, (2363)
"Great location and staff!"
United States
Laura
Florida Hotel & Conference Center in the Florida Mall
Indoor pool, pool umbrellas, sun loungers
Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis

Vacation Home in Lindfields

Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis
5.0 star property
The price is ￥28,849
￥60,033 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis
Front of property
Willow Bend

Vacation Home in Crescent Lakes

Willow Bend
4.0 star property
10.0 out of 10, Exceptional, (2)
"this house abuts woods and a slow river that made the property peaceful "
United States
John
The price is ￥27,946
￥93,559 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Willow Bend
Interior
Charming 2-bedroom apartment in house with AC, WiFi included

Vacation Home in Apopka

Charming 2-bedroom apartment in house with AC, WiFi included
9.8 out of 10, Exceptional, (13)
"It was quiet, clean and had snacks and drinks for us."
United States
Lori
The price is ￥16,160
￥23,060 total
includes taxes & fees
Dec 28 - Dec 29
Charming 2-bedroom apartment in house with AC, WiFi included
Dock
Barefoot Suites

Aparthotel in Kissimmee

Barefoot Suites
3.0 star property
9.0 out of 10, Wonderful, (1801)
"Clean room location "
United States
Bryan
Barefoot Suites
Fridge, microwave, oven, stovetop
Renovated Peaceful Luxury Walk to Mall Park Publix

Vacation Home in Altamonte Springs

Renovated Peaceful Luxury Walk to Mall Park Publix
9.4 out of 10, Exceptional, (13)
"Beautiful place. Great customer service."
United States
Carolyn N.
The price is ￥13,350
￥29,443 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Renovated Peaceful Luxury Walk to Mall Park Publix
1 bedroom, iron/ironing board, free WiFi, bed sheets
The Cozy Crash Pad: Tiny House Experience

Vacation Home in Orlando

The Cozy Crash Pad: Tiny House Experience
9.0 out of 10, Wonderful, (22)
"It was incredible! The tiny home feels incredibly cozy and was super easy to find. We had a wonderful visit."
United States
Tristen H.
The price is ￥9,993
￥23,148 total
includes taxes & fees
Jan 18 - Jan 19, 2026
The Cozy Crash Pad: Tiny House Experience
Free WiFi, bed sheets
Downtown Private Efficiency Lake Eola Central Business District

Apartment in Downtown Orlando

Downtown Private Efficiency Lake Eola Central Business District
9.4 out of 10, Exceptional, (48)
"Great location has everything you need for a short stay! "
United States
MEAGAN
The price is ￥9,122
￥22,152 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Downtown Private Efficiency Lake Eola Central Business District
Indoor pool, 2 outdoor pools, open 8:00 AM to 8:00 PM, pool umbrellas
Premium Condos near Universal Studios

Condo resort in International Drive District

Premium Condos near Universal Studios
3.5 star property
9.2 out of 10, Wonderful, (25)
"Awesome place. "
United States
Ryan
The price is ￥12,193
￥24,081 total
includes taxes & fees
Jan 26 - Jan 27, 2026
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.
View all properties
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

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Clean room, quiet hotel rooms"
Daniel 4-night trip
Posted 17 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

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
  • Use the map to find apartments and other holiday homes in the Windermere neighbourhood you prefer
  • 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 13 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.