Holiday Rentals in Windermere

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Our top choices for Windermere holiday rentals

The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is €493
includes taxes & fees
9 Feb - 10 Feb
The Farm House - Great Location + Pet Friendly!

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
The price is €272
includes taxes & fees
9 Feb - 10 Feb
Shore Steps Cottage - Walking Distance To The Town Of Windermere

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.6 out of 10, Good, (1,007 reviews)
"Staff was very helpful, location was what we needed and rooms and pool were outstanding "
United States
Chester Joseph
The price is €87
includes taxes & fees
9 Feb - 10 Feb
voco Kissimmee Orlando by IHG

Fairfield Inn & Suites Orlando Int'l Drive/Convention Center

Fairfield Inn & Suites Orlando Int'l Drive/Convention Center
2.5 star property
International Drive District
8.6 out of 10, Excellent, (1,004 reviews)
"Excelent location, clean room and the staff is great"
United States
Maite
The price is €94
includes taxes & fees
24 Feb - 25 Feb
Fairfield Inn & Suites Orlando Int'l Drive/Convention Center

The Point by Edge

The Point by Edge
4.0 star property
Florida Center
8.4 out of 10, Very good, (874 reviews)
"Nice place. "
Canada
Patrick
The price is €76
includes taxes & fees
3 Mar - 4 Mar
The Point by Edge

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,283 reviews)
"Yes .. very clean rooms and hotel chef was great"
United States
Alicia
The price is €103
includes taxes & fees
25 Feb - 26 Feb
Vacation Village Orlando, Celebration

The View Studio Suites and Event Venue

The View Studio Suites and Event Venue
3.0 star property
Orlando
8.4 out of 10, Very good, (1,606 reviews)
"Clean and spacious rooms and the breakfast was great."
United States
Karen
The price is €82
includes taxes & fees
8 Feb - 9 Feb
The View Studio Suites and Event Venue

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,820 reviews)
"Great place. To stay "
United States
THOMAS
Barefoot Suites

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very good, (3,060 reviews)
"Overall the stay was great. Staff were very helpful. We had some issues with the room carpet but it was taken care of as soon as I reported to the front desk. I very much recommend this place."
United States
Lucia
The price is €322
includes taxes & fees
9 Mar - 10 Mar
Regal Oaks Resort Vacation Townhomes by IDILIQ

Suite Near Universal Studios w Pool & Hot Tub

Suite Near Universal Studios w Pool & Hot Tub
3.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"The room was clean and service was great!"
United States
Daija
The price is €160
includes taxes & fees
25 Feb - 26 Feb
Suite Near Universal Studios w Pool & Hot Tub

Beautiful Studio near Int. Drive, Disney & Airport.

Beautiful Studio near Int. Drive, Disney & Airport.
Conway
9.4 out of 10, Exceptional, (18 reviews)
"The property is minimal but enhouses everything we needed. Great place to stay. "
United States
JoAnn E.
The price is €138
includes taxes & fees
8 Feb - 9 Feb
Beautiful Studio near Int. Drive, Disney & Airport.

Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (54 reviews)
"The place was surprisingly spacious and super clean.The area is very nice and quiet."
United States
Awilda A.
The price is €113
includes taxes & fees
17 Feb - 18 Feb
Private guest studio in the heart of orlando.

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 €223
includes taxes & fees
8 Feb - 9 Feb
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1,794 reviews)
"Cottage was very clean and easy check in close to all dining and shopping "
United States
Fernando
The price is €371
includes taxes & fees
10 Feb - 11 Feb
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
Davenport
9.2 out of 10, Wonderful, (526 reviews)
"It was lovely! We would stay here again for sure! "
United States
Hilary
The price is €133
includes taxes & fees
8 Feb - 9 Feb
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (201 reviews)
"Great place. Great location. "
United States
Andrew
The price is €116
includes taxes & fees
22 Feb - 23 Feb
Barefoot'n Resort Kissimmee Orlando

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.
Cozy Private Apartment - Stylish & Spotless — No sharing areas

Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.4 out of 10, Exceptional, (32 reviews)
"Our experience at this condo was excellent. The room was spotless and comfortable, and the space felt very safe and quiet. Parking was easy, and grocery stores and dining options were close by which made our trip convenient. The balcony view was a nice touch for morning coffee, and the AC kept the unit perfectly cool during our stay. Overall, a great location especially for Disney travelers. Highly recommend!"
United States
Kristy
The price is €119
includes taxes & fees
11 Feb - 12 Feb
Sunset Bliss Retreat Condo - Near Disney

Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis

Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis
5.0 star property
Lindfields
Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis

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 €158
includes taxes & fees
9 Feb - 10 Feb
NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
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

Find out more about Windermere

Everything you need to know about Windermere holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windermere holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windermere holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windermere holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windermere. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windermere holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windermere holiday rentals we have selected for you start as low as €76 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windermere rentals

At Expedia, we put the best Windermere holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windermere rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windermere holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windermere. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 4 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.