A lakeside community with houses and boats.

Windermere Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Windermere vacation rentals

A serene landscape with a pond, trees with Spanish moss, and a palm tree.

1. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
$351 nightly
The price is $390
Oct 2 - Oct 3
Total with taxes and fees
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Private kitchen

2. Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
4.0 star property
Windermere
$531 nightly
The price is $589
Oct 5 - Oct 6
Total with taxes and fees
Rustic Hideaway - Great Location + Pet Friendly!
A swimming pool with lounge chairs and palm trees.

3. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,358 reviews)
"Enjoyed our stay and felt it was a great price for the location."
United States
Lisa
$84 nightly
The price is $94
Oct 21 - Oct 22
Total with taxes and fees
The Point Hotel & Suites Orlando
A resort pool area with palm trees, lounge chairs, and umbrellas.

4. Marriott's Grande Vista

Marriott's Grande Vista
4.0 star property
Orlando
9.0 out of 10, Wonderful, (5,078 reviews)
"Great place to stay,"
United States
Andy
$96 nightly
The price is $108
Oct 27 - Oct 28
Total with taxes and fees
Marriott's Grande Vista
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

5. The View Hotel, Trademark Collection by Wyndham

The View Hotel, Trademark Collection by Wyndham
3.0 star property
Orlando
8.4 out of 10, Very good, (2,159 reviews)
"Everything was amazing. Easy check in and check out, great location and quiet place. Breakfast was great and the food was excellent excellent."
United States
Breila
$79 nightly
The price is $89
Nov 1 - Nov 2
Total with taxes and fees
The View Hotel, Trademark Collection by Wyndham
Children's play area - outdoor

6. Floridays Resort Orlando

Floridays Resort Orlando
4.0 star property
International Drive District
8.6 out of 10, Excellent, (12,143 reviews)
"The service was great"
United States
Maria
$143 nightly
The price is $160
Oct 4 - Oct 5
Total with taxes and fees
Floridays Resort Orlando
A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

7. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (5,102 reviews)
"Great place"
United States
Wilbert
$103 nightly
The price is $117
Oct 18 - Oct 19
Total with taxes and fees
Vacation Village Orlando, Celebration
A covered outdoor swimming pool area with lounge chairs, a clock, and a sign indicating spa rules and no diving.

8. Blue Tree Resort at Lake Buena Vista

Blue Tree Resort at Lake Buena Vista
3.0 star property
Orlando
8.6 out of 10, Excellent, (2,076 reviews)
"It was clean nice property, easy access"
United States
Mohammad
$104 nightly
The price is $117
Oct 2 - Oct 3
Total with taxes and fees
Blue Tree Resort at Lake Buena Vista
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

9. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
9.0 out of 10, Wonderful, (2,290 reviews)
"Clean property, friendly staff, close to everything!"
United States
Matthew
$398 nightly
The price is $451
Oct 26 - Oct 27
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Exterior

10. WorldQuest Orlando Resort

WorldQuest Orlando Resort
4.0 star property
Orlando
8.4 out of 10, Very good, (4,096 reviews)
"One of my favorite places to stay in Orlando"
United States
Jodi
$296 nightly
The price is $333
Oct 2 - Oct 3
Total with taxes and fees
WorldQuest Orlando Resort
A modern lobby with a wooden ceiling, a TV mounted on a wooden panel, and a seating area with blue chairs and a white sofa.

11. Marriott's Royal Palms

Marriott's Royal Palms
4.0 star property
Orlando
9.4 out of 10, Exceptional, (323 reviews)
"Place is minutes from away from Disney Springs and major attractions, clean and modern, with a wonderful golf course."
United States
Ernie
$196 nightly
The price is $221
Oct 31 - Nov 1
Total with taxes and fees
Marriott's Royal Palms
A covered swimming pool with a view of the surrounding garden and trees.

12. Mini golf course, 1 mile to Universal, Pool

Mini golf course, 1 mile to Universal, Pool
Orlando
10.0 out of 10, Exceptional, (36 reviews)
"Family friendly great location to Parks "
United States
Joe R.
$471 nightly
The price is $516
Oct 18 - Oct 19
Total with taxes and fees
Mini golf course, 1 mile to Universal, Pool
A water slide structure with a person at the bottom of the slide, water splashing around.

13. The Cabins at Disney's Fort Wilderness Resort

The Cabins at Disney's Fort Wilderness Resort
4.5 star property
Bay Lake
9.2 out of 10, Wonderful, (571 reviews)
"Pet friendly"
United States
Darren
$590 nightly
The price is $664
Oct 5 - Oct 6
Total with taxes and fees
The Cabins at Disney's Fort Wilderness Resort
A resort pool with a central water feature, surrounded by palm trees and lounge chairs.

14. Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
4.0 star property
International Drive District
9.2 out of 10, Wonderful, (4,082 reviews)
"Great place to stay with the family."
United States
Vanessa
$96 nightly
The price is $108
Oct 26 - Oct 27
Total with taxes and fees
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
A modern kitchen with dark wood cabinets, a granite countertop, and a central island. There is a dining area with a table and chairs, and a view of the outside through large windows.

15. Century Millenia

Century Millenia
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (149 reviews)
"Absolutely amazing and perfect will be back here everytime!"
United States
Arianna
$204 nightly
The price is $220
Oct 25 - Oct 26
Total with taxes and fees
Century Millenia
A patio with Adirondack chairs and a round table, surrounded by palm trees and a brick floor.

16. Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort

Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
3.5 star property
International Drive District
9.2 out of 10, Wonderful, (279 reviews)
"Great apartments, perfect for families exploring Universal and the wider Orlando area."
United Kingdom
Niki
$163 nightly
The price is $183
Nov 1 - Nov 2
Total with taxes and fees
Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
A modern bedroom with a large bed, a bedside table, a wooden dresser, and a hanging light fixture.

17. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (334 reviews)
"Establishment with meticulously designed in, which made it very comfortable. I enjoyed my stay tremendously. The communication of the staff was amazing, our room is immaculate, a bar had a very in fighting comforting environment very clean get place to socialize with friends and family.I will see you next year the same time."
United States
Sondria
$77 nightly
The price is $86
Oct 6 - Oct 7
Total with taxes and fees
Suites by The Wellborn
A swimming pool with lounge chairs and palm trees.

18. staySky Suites - I Drive Orlando

staySky Suites - I Drive Orlando
3.0 star property
International Drive District
7.8 out of 10, Good, (1,301 reviews)
"Clean, nice staff, great location"
United States
Cynthia
$93 nightly
The price is $105
Oct 11 - Oct 12
Total with taxes and fees
staySky Suites - I Drive Orlando
A golf course with a large rock formation, palm trees, and a well-maintained green.

19. 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, (580 reviews)
"First time experience. The stay was pretty good."
United States
Anquanice
$118 nightly
The price is $132
Oct 4 - Oct 5
Total with taxes and fees
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
A hotel with a swimming pool, palm trees, and outdoor seating areas.

20. Club Wyndham Cypress Palms

Club Wyndham Cypress Palms
3.5 star property
Kissimmee
9.0 out of 10, Wonderful, (1,980 reviews)
"The place was nice clean and amazing will return in December"
United States
Natarisha
$139 nightly
The price is $158
Oct 14 - Oct 15
Total with taxes and fees
Club Wyndham Cypress Palms
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

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"N/A"
Carlos 1-night trip
Posted less than an hour ago
Westgate Lakes Resort & Spa Universal Studios Area

Find out more about Windermere

Everything you need to know about Windermere vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windermere vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windermere vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windermere in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $89 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windermere rentals

At Expedia, we put the best Windermere vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Formosa Valley Resort by UNE Homes: You might want to consider this Windermere vacation home rental for your stay. It is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

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.