A lakeside community with houses and boats.

Windermere Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Windermere vacation rentals

Exterior

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,488 reviews)
"Great stay"
United States
Martena
The price is P4,208
P6,314 total
includes taxes & fees
Jul 26 - Jul 27
Vacation Village Orlando, Celebration
Interior

Upstay: Family-friendly Getaway With Spa & Pool

Upstay: Family-friendly Getaway With Spa & Pool
3.5 star property
Orlando
10.0 out of 10, Exceptional, (1 review)
"Clean room"
United States
Yves marie
The price is P6,635
P16,381 total
includes taxes & fees
Jul 12 - Jul 13
Upstay: Family-friendly Getaway With Spa & Pool
2 outdoor pools, open 7:00 AM to 11:00 PM, free cabanas, pool umbrellas

Magical Moment Vacation Condos

Magical Moment Vacation Condos
4.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"Very Clean room staff were great !! Definitely would stay again !"
United States
stephanie
The price is P5,916
P21,020 total
includes taxes & fees
Jul 12 - Jul 13
Magical Moment Vacation Condos
Living area

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 P6,267
P17,418 total
includes taxes & fees
Jul 14 - Jul 15
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
Outdoor pool

The Irlo

The Irlo
3.0 star property
Kissimmee
7.4 out of 10, Good, (48 reviews)
"Room was nice, staff was friendly. Location was perfect for my needs"
United States
Amanda
The price is P3,502
P5,369 total
includes taxes & fees
Jul 26 - Jul 27
The Irlo
Interior

Upstay: Stylish 3BR Condo w Pationear Disney

Upstay: Stylish 3BR Condo w Pationear Disney
4.0 star property
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"Great for family’s. Very clean ,great prices"
United States
Christine
The price is P7,065
P18,247 total
includes taxes & fees
Aug 7 - Aug 8
Upstay: Stylish 3BR Condo w Pationear Disney
Interior entrance

Family Friendly Davenport Pool Villa

Family Friendly Davenport Pool Villa
4.0 star property
Florida Pines
8.0 out of 10, Very Good, (1 review)
"The villa was very clean, it was in a quiet community. The private pool was amazing. It was very relaxing for my family and a baby. Only downside was we had to go out and buy more toilet paper, paper towels, salt/pepper, and a large fan. Some of the rooms would get pretty warm since the AC can’t be set past 74. But, overall it was a nice stay! We would stay there again in the future!"
United States
Joseph
The price is P9,830
P33,580 total
includes taxes & fees
Jul 13 - Jul 14
Family Friendly Davenport Pool Villa
Exterior

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.2 out of 10, Wonderful, (332 reviews)
"Great location and clean spacious and comfortable"
United States
Michele
The price is P7,457
P9,231 total
includes taxes & fees
Jul 13 - Jul 14
Barefoot'n Resort Kissimmee Orlando
Private kitchen

Century Millenia

Century Millenia
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (139 reviews)
"Simple place for us to stay while visiting Orlando."
United States
Chimere
The price is P6,986
P12,467 total
includes taxes & fees
Jul 26 - Jul 27
Century Millenia
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
"Our experience was amazing! The property was beautiful and clean and the rooms were also. The friendliness and helpfulness of the staff was top tier and definitely a determining factor as my family and I choosing to stay at this hotel in the future. The pool and other amenities were also cool. We will be back!"
Keisha 1-night trip
Posted 5 hours 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: 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.