Windermere Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Windermere

Avanti International Resort
3.0 star property
7.8 out of 10, Good, (2145)
"Excelente and create attention and clear "
The price is NZ$135
per night
30 Jun - 1 Jul
Avanti International Resort
Lake Buena Vista Resort Village & Spa
4.0 star property
8.4 out of 10, Very good, (7298)
"Trash cans were little had to change often"
The price is NZ$362
per night
9 Jun - 10 Jun
Lake Buena Vista Resort Village & Spa
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4895)
"Whenever I return to Orlando I will stay here. The staff was so polite and helpful. So comfortable"
The price is NZ$383
per night
5 Jun - 6 Jun
Hyatt Regency Orlando International Airport
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
3.5 star property
8.6 out of 10, Excellent, (3170)
"Can’t complain!! Our stay was excellent. I didn’t use the transportation but it was offered. Our stay was for 5 days with 3 teenagers 14, 16, and 17 year olds they enjoyed it. We were 5 people in total and everything was great!! "
The price is NZ$162
per night
10 Jun - 11 Jun
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (5996)
"Easy parking"
The price is NZ$81
per night
9 Jun - 10 Jun
Ramada by Wyndham Kissimmee Gateway
CoCo Key Hotel and Water Resort 
3.5 star property
7.4 out of 10, Good, (3795)
"Definitely would visit again! "
The price is NZ$161
per night
16 Jun - 17 Jun
CoCo Key Hotel and Water Resort 
Floridays Resort Orlando
3.5 star property
8.6 out of 10, Excellent, (10709)
"Excellent experience "
The price is NZ$269
per night
11 Jun - 12 Jun
Floridays Resort Orlando
Embassy Suites by Hilton Orlando International Dr ICON Park
3.5 star property
8.6 out of 10, Excellent, (1529)
"Smaller beds to fit 2 ppl comfortably. Other than that clean and quite property. "
The price is NZ$232
per night
11 Jun - 12 Jun
Embassy Suites by Hilton Orlando International Dr ICON Park
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
3.0 star property
7.0 out of 10, Good, (2455)
"Everything was very good, I liked it"
The price is NZ$240
per night
5 Jun - 6 Jun
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Holiday Inn & Suites Across From Universal Orlando, an IHG Hotel
3.0 star property
7.2 out of 10, Good, (577)
"The rooms were big and clean, staff was friendly "
The price is NZ$162
per night
10 Jun - 11 Jun
Holiday Inn & Suites Across From Universal Orlando, an IHG Hotel
Wingate by Wyndham - Orlando International Airport
3.0 star property
8.8 out of 10, Excellent, (4017)
"Great stay after late flight and filling breakfast in the morning."
The price is NZ$171
per night
17 Jun - 18 Jun
Wingate by Wyndham - Orlando International Airport
Flamingo Waterpark Resort
3.0 star property
6.8 out of 10, (1168)
"Una estadía amena, el personal muy atento y cerca de muchas cosas. El parque de aguas excelente para las atracciones que tiene."
The price is NZ$140
per night
18 Jun - 19 Jun
Flamingo Waterpark Resort
The View Studio Suites and Event Venue
3.5 star property
8.4 out of 10, Very good, (212)
"Nice and clean property "
The price is NZ$132
per night
1 Jul - 2 Jul
The View Studio Suites and Event Venue
Summer Bay Orlando by Exploria Resorts
3.5 star property
8.4 out of 10, Very good, (4755)
"Had a great time. Beautiful resort. This is my 2nd time here and I definitely would come back again. "
The price is NZ$251
per night
5 Jun - 6 Jun
Summer Bay Orlando by Exploria Resorts
Seralago Hotel & Suites Main Gate East
3.0 star property
5.2 out of 10, (5294)
"Very basic nothing to brag about "
The price is NZ$76
per night
16 Jun - 17 Jun
Seralago Hotel & Suites Main Gate East
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (1454)
"I enjoyed my stay at the hotel on my girls trip memorial weekend.. The room was nice and roomy enough for 4.. My issue with this whole booking is the fact that Expedia states there is a car charger on site but there isn’t one.. That issue needs to be rectified as this is false advertisement to anyone like myself who rented a electric car and chose this hotel for that specific reason.."
The price is NZ$159
per night
9 Jun - 10 Jun
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (849)
"Property was absolutely beautiful! The cottages were amazing! We got to use the amenities after checking out. I would highly recommend this place with families with children. If you want to go to a resort to relax by the pool, this isn’t it, this is more for people with families. The cottages are well equipped for families. Overall his beautiful !!"
Margaritaville Resort Orlando Cottages by Rentyl
Vacation Village at Parkway
3.0 star property
8.2 out of 10, Very good, (1270)
"Rooms and facilities need updating"
Vacation Village at Parkway
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1420)
"The unit is very spacious, full kitchen and full size washer and dryer. Nice pool area, not crowded "
The Berkley, Orlando
Embassy Suites by Hilton Orlando Lake Buena Vista South
3.5 star property
9.2 out of 10, Wonderful, (1720)
"Loved the property, we had an amazing time without even leaving the property!! Free adult beverages, great dining options, and great customer service!! "
The price is NZ$234
per night
9 Jun - 10 Jun
Embassy Suites by Hilton Orlando Lake Buena Vista South
Don't see what you're looking for?
See all available properties in Windermere
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.

Other types of properties in Windermere you may be interested in

The Grove Resort & Water Park Orlando
4.0 star property
8.2 out of 10, Very good, (5490)
"Nice area. Near Disney and places to buy groceries, food and gas. It is on a new development area. "
The price is NZ$362
per night
5 Jun - 6 Jun
The Grove Resort & Water Park Orlando
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
3.5 star property
6.4 out of 10, (5512)
"Very nice property "
The price is NZ$157
per night
6 Jun - 7 Jun
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Universal's Endless Summer Resort - Dockside Inn and Suites
3.0 star property
9.0 out of 10, Wonderful, (5187)
"Great property. Very convenient. Only con is walls are thin. You hear people in halls all hours of the night "
The price is NZ$342
per night
5 Jun - 6 Jun
Universal's Endless Summer Resort - Dockside Inn and Suites
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windermere holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windermere. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windermere. Seeing all the best attractions is bound to make you fall in love with Windermere. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windermere short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Windermere?

Yes, we have holiday rentals where you'll be only 4.1 mi (6.6 km) from Universal Studios Florida, offering you a more 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 are some of the best holiday rentals that Windermere has to offer?

The Berkley, Orlando: This holiday home rental outside of Windermere offers a furnished patio, a terrace and a BBQ 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 holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Windermere?

Expedia has 11 holiday 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 wider area, you’ll find popular places such as Universal Studios Florida and Universal Orlando Resort.

What’s a holiday rental in Windermere like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windermere. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.

Recent reviews of Windermere properties
Expedia verified reviews