Windermere, FL Villas Rentals

A lakeside community with houses and boats.

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Our top choices for Windermere villas

1. Rustic Hideaway - Great Location + Pet Friendly!

Windermere

$505 nightly

Sep 17 - Sep 18

Total with taxes and fees

2. SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging

College Park

Judah E.

$164 nightly

Sep 27 - Sep 28

Total with taxes and fees

3. 4,800 sf Estate | Pool, Lake, Weddings and Events

Orlando

Hidden Gem C.

$956 nightly

Sep 17 - Sep 18

Total with taxes and fees

4. Family Friendly Villa near Disney, pool, sleeps 5

Vacation Village

Amy E.

$229 nightly

Sep 17 - Sep 18

Total with taxes and fees

5. 3BR Townhouse Right in Front of Epic Universe!

Orlando

Hal J.

$417 nightly

Sep 17 - Sep 18

Total with taxes and fees

6. Emerald Garden - Resort - 15 Min to Disney - Pets

Kissimmee

$385 nightly

Sep 17 - Sep 18

Total with taxes and fees

7. Contemporary 4BR Townhome With Pool & Themed Rooms

Clermont

Malyjah

$293 nightly

Sep 21 - Sep 22

Total with taxes and fees

8. 7BR Lakefront | Pool & Hot Tub

Edgewood

Omer H.

$539 nightly

Sep 21 - Sep 22

Total with taxes and fees

9. Amazing Spider | Disney, Slides & River

Kissimmee

$271 nightly

Sep 17 - Sep 18

Total with taxes and fees

10. 10BR Villa Near Disney, Pool and Resort Waterpark

Kissimmee

Jefferson C.

$620 nightly

Sep 17 - Sep 18

Total with taxes and fees

11. Family 5BR w/ Pool & Grill Near Disney Magic

Kissimmee

$528 nightly

Sep 30 - Oct 1

Total with taxes and fees

12. Shiny Legendary | Disney, River & Slides

Kissimmee

Aren B.

$271 nightly

Sep 20 - Sep 21

Total with taxes and fees

13. At Lakes Upscale Villa/Next to Downtown Orlando

Lake Davis - Greenwood

Wilbur B.

$469 nightly

Sep 23 - Sep 24

Total with taxes and fees

14. Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!

Kissimmee

Cheryl D.

$823 nightly

Sep 18 - Sep 19

Total with taxes and fees

15. Charming Villa near Disney, pool, 4 beds, sleeps 5

Vacation Village

Joe H.

$232 nightly

Sep 20 - Sep 21

Total with taxes and fees

16. Cozy 3bd Townhouse | Near Disney| Encantada Resort

Kissimmee

"I was looking for a place to escape for a few days while getting my bathroom redone and the property checked all of the boxes. My wife was able to get some work done, my dog had more than enough space, and the location is minutes from the amusement parks and tons of restaurants.The property is gated, clean, and has multiple bedrooms and bathrooms for the larger families that need it. The host was more than attentive. Even when I was having issues with the television, he responded to my message...

LEONARD W.

$389 nightly

Sep 27 - Sep 28

Total with taxes and fees

17. Upstay: Modern Family Townhome With Pool & Patio

Clermont

$293 nightly

Sep 17 - Sep 18

Total with taxes and fees

18. 8 Mi to Disney: Villa w/ Screened Pool & Lanai

Kissimmee

Darlene K.

$373 nightly

Sep 21 - Sep 22

Total with taxes and fees

19. Enchanted Villa with Lake View 6-Bedroom in Resort

Lake Berkley

Sarah J.

$407 nightly

Sep 17 - Sep 18

Total with taxes and fees

20. Galactic 7-Bedroom Villa 3 Miles to Disney Star Wars Galaxy Edge

Kissimmee

Alyssa J.

$431 nightly

Sep 21 - Sep 22

Total with taxes and fees

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Top Windermere Hotel Reviews

Universal's Cabana Bay Beach Resort

8/10 Good

"Great stay, had an upgrade to a suite brilliant will definitely book again"

Kompose Boutique Resort at Theme Parks

8/10 Good

"Overall a great hotel for the money. Staff were excellent. Rooms were very clean and beds were comfortable. Very little furniture in the room and the shower was only partially closed allowing water to spill onto the floor and cold air to enter. Elevators are very far from most of the rooms. Breakfast was better than most hotels I have stayed at. I would definitely stay at this hotel again."

Marriott's Grande Vista

8/10 Good

"Marriott has a great location with close proximity to Sea World. I was a bit surprised by the amount of the required deposit ($500) at check in.. In addition to the $30 per day self-parking charge (valet is NOT available); I was out of $750 at check in. That meant I essentially paid for my stay once online and then at check in I paid about 85% of that price AGAIN in deposits and parking fees. Also I was SHOCKED to find house-keeping was an ADDITIONAL fee on top of all of this. I thought for a five night stay there would be at least ONE housekeeping session included.. NOT AT ALL. Aside from the absolute nickel and dime fees for EVERYTHING and the VERY aggressive sales pressure to buy their timeshares package. The room was great. The location very convenient. Just be prepared for a substantial deposit when you stay here and beware that they are VERY aggressive in trying to get you to their timeshare sales presentation. A plus is also that their pools stay open until 11pm and they have multiple pools on site."

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"One of the best hotels in Orlando. It has everything a Disney resort should have but doesn’t.The front desk was incredibly helpful and greeted you every time you walked through the door. They were very hospitable and knew their property well. The dining and bar staff were amazing and friendly. The kickback and breakfast was a very much needed accommodation, especially if you’re on a budget. The breakfast was pretty good with a great selection and a waffle iron that featured Mickey’s imprint. Pretty cute. Something like that would have costed $7-10 at Disney. The shuttle bus service was a plus but can get packed fast, so have your key card ready for verification. In all, this hotel has everything needed."

Find out more about Windermere

Windermere Villas information

Number of reviews	271
Accommodation	9822 Villas
Lowest Price	$182
Highest Price	$1,061

Frequently asked questions

How much do villas in Windermere cost?

You'll pay between $182 and $1,061 per night for villas in Windermere. Whatever your budget, an epic escape is only a few clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What are the best villas in Windermere?

Windermere has multiple villas with a total average guest review rating of 9.6. Villa Manuel Lakeview 3 Bedroom Condo By Redawning is a popular option with Expedia guests. Visitors staying at this 3.5-star property will have use of a barbecue grill and a swimming pool. Westgate Lakes Resort And Spa is another much-loved stay. This 3.5-star villa offers an outdoor entertainment area and a cafe, among other conveniences.

How many villas are there in Windermere?

Reclaim your vacation days and pick from 9822 villas in Windermere. For a family adventure, a romantic break or anything in between, Expedia can help you find the right place in a few simple clicks.

Are there any family-friendly villas in Windermere?

Get cozy at Villa Manuel Lakeview 3 Bedroom Condo By Redawning, a 3.5-star option only a quick drive from town. Amenities here include a playground and a barbecue grill. Another family-friendly getaway is Westgate Lakes Resort And Spa. A barbecue grill and a cafe help make this 3.5-star villa a favorite among travelers. Once you've checked in and unpacked your things, there are tons of family-friendly attractions to visit around Windermere. Walt Disney World® Resort and Universal Studios Florida guarantee fun for all ages.

Why book your villa in Windermere with Expedia?

With Expedia, it's easy to find your dream villa in Windermere. Vacationing with the kids? Take advantage of our filters to search for stays with amenities like free WiFi. If you have a budget, select how much you're willing to spend and the star rating of the property. We'll help you find the perfect place that suits your taste and style.

How can I find cheap villas in Windermere?

A great way to score cheap villas in Windermere is with Expedia's filter tool. Tailor your search results by amenities, budget and star rating to discover unbeatable deals in just a few clicks.

What is there to do near my villa in Windermere?

Once you've unpacked your suitcases, set out and discover the incredible things Windermere has to offer. Isleworth Golf and Country Club is a top attraction to add to your must-see list.

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Things to do in Windermere

Villas in Windermere

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Upfront pricing

Check prices for these dates

Our top choices for Windermere villas

1. Rustic Hideaway - Great Location + Pet Friendly!

2. SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging

3. 4,800 sf Estate | Pool, Lake, Weddings and Events

4. Family Friendly Villa near Disney, pool, sleeps 5

5. 3BR Townhouse Right in Front of Epic Universe!

6. Emerald Garden - Resort - 15 Min to Disney - Pets

7. Contemporary 4BR Townhome With Pool & Themed Rooms

8. 7BR Lakefront | Pool & Hot Tub

9. Amazing Spider | Disney, Slides & River

10. 10BR Villa Near Disney, Pool and Resort Waterpark

11. Family 5BR w/ Pool & Grill Near Disney Magic

12. Shiny Legendary | Disney, River & Slides

13. At Lakes Upscale Villa/Next to Downtown Orlando

14. Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!

15. Charming Villa near Disney, pool, 4 beds, sleeps 5

16. Cozy 3bd Townhouse | Near Disney| Encantada Resort

17. Upstay: Modern Family Townhome With Pool & Patio

18. 8 Mi to Disney: Villa w/ Screened Pool & Lanai

19. Enchanted Villa with Lake View 6-Bedroom in Resort

20. Galactic 7-Bedroom Villa 3 Miles to Disney Star Wars Galaxy Edge

Find vacation rentals that suit your style

Top Windermere Hotel Reviews

Universal's Cabana Bay Beach Resort

Find out more about Windermere

Windermere Villas information

Frequently asked questions

Explore a world of travel with Expedia