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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Windermere condo rentals

Exterior

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Kissimmee
9.2 out of 10, Wonderful, (164 reviews)
"Excellent accommodations."
United States
Raychelle
$188 nightly
The price is $210
May 20 - May 21
Total with taxes and fees
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
7 outdoor pools, pool umbrellas, sun loungers

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,161 reviews)
"Fanily friendly, great value, great location!"
United States
Marivette
$103 nightly
The price is $117
Jun 2 - Jun 3
Total with taxes and fees
Vacation Village Orlando, Celebration
Condo, 2 Bedrooms | Exterior

Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo

Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"we had a great time and enjoyed the condo for the short time we were there."
United States
Sherri Ann
$459 nightly
The price is $521
May 20 - May 21
Total with taxes and fees
Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo
TV, offices

Bright Ground Floor Condo Minutes to Parks

Bright Ground Floor Condo Minutes to Parks
Kissimmee
$275 nightly
The price is $292
May 21 - May 22
Total with taxes and fees
Bright Ground Floor Condo Minutes to Parks
Dining

2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access

2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access
Vacation Village
10.0 out of 10, Exceptional, (8 reviews)
"Excellent host, very clean, coffee bar, and access to great facilities. Would highly recommend this place."
United States
Jodi
$248 nightly
The price is $272
May 20 - May 21
Total with taxes and fees
2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access
Interior

Upstay - Condo w Pool and More - Near Disney

Upstay - Condo w Pool and More - Near Disney
Winter Garden
9.0 out of 10, Wonderful, (22 reviews)
"Great place! Convenient, cozy and clean!"
United States
SHARLA B.
$238 nightly
The price is $266
May 20 - May 21
Total with taxes and fees
Upstay - Condo w Pool and More - Near Disney
Miscellaneous

Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park
South Eola
9.4 out of 10, Exceptional, (6 reviews)
"Clean, easy stay. Great experience for what we needed."
United States
Neil L.
$171 nightly
The price is $190
May 20 - May 21
Total with taxes and fees
Retro lake Eola 1 Bedroom Condo Thornton park
Smart TV

Vintage 2 Bedroom Condo Lake Eola View

Vintage 2 Bedroom Condo Lake Eola View
South Eola
10.0 out of 10, Exceptional, (11 reviews)
"The place was clean and spacious. The living room was our relaxing spot. The location was great as we can see the lake.The location was safe and had a great parking spot. The host was quick to respond for any inquiries and would definitely stay here again. "
United States
Nagendra A.
$188 nightly
The price is $209
May 20 - May 21
Total with taxes and fees
Vintage 2 Bedroom Condo Lake Eola View
Fridge, microwave, oven, stovetop

Renovated Condo Lake Eola View Great Location

Renovated Condo Lake Eola View Great Location
South Eola
10.0 out of 10, Exceptional, (18 reviews)
"Great place to stay! Quiet and in a great neighborhood! "
United States
Nick L.
$193 nightly
The price is $215
May 20 - May 21
Total with taxes and fees
Renovated Condo Lake Eola View Great Location
Fridge, microwave, oven, stovetop

BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️

BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️
Kissimmee
10.0 out of 10, Exceptional, (13 reviews)
"Home was clean, loved the wine when we arrived late and easy access"
United States
Denis B.
$299 nightly
The price is $334
May 20 - May 21
Total with taxes and fees
BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️
Outdoor pool, a heated pool

Vibrant, Modern Condo, Storey Lake Resort, within minutes of Orlando Attractions

Vibrant, Modern Condo, Storey Lake Resort, within minutes of Orlando Attractions
Kissimmee
9.8 out of 10, Exceptional, (30 reviews)
"Easy check in and communication. Condo was clean and would stay there again with my family. "
United States
Jeraka I.
$277 nightly
The price is $310
May 20 - May 21
Total with taxes and fees
Vibrant, Modern Condo, Storey Lake Resort, within minutes of Orlando Attractions
Pool

Spacious Home in FantasyWorld

Spacious Home in FantasyWorld
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Thanks you so much for everything for sure this place is AMAZING, everything went perfect and resort staff was very nice and helpful all the time and yes is same as the pictures and eve more better in person. "
United States
Harley Gustavo
$317 nightly
The price is $336
Jun 3 - Jun 4
Total with taxes and fees
Spacious Home in FantasyWorld
Condo, 4 Bedrooms | Lobby

Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo

Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
$560 nightly
The price is $560
May 20 - May 21
Total with taxes and fees
Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo
Fridge, microwave, oven, stovetop

Luxe King Suite Bliss Getaway Condo Near Disney

Luxe King Suite Bliss Getaway Condo Near Disney
Kissimmee
9.2 out of 10, Wonderful, (34 reviews)
"Everything was perfect; location and shopping "
United States
Shandell E.
$146 nightly
The price is $163
May 23 - May 24
Total with taxes and fees
Luxe King Suite Bliss Getaway Condo Near Disney
Exterior

Reunion Resort - Near Theme Parks & Airport

Reunion Resort - Near Theme Parks & Airport
Reunion
9.6 out of 10, Exceptional, (57 reviews)
"Had a as great stay at Reunion, fabulous facilities. "
United States
Helen H.
$278 nightly
The price is $311
May 23 - May 24
Total with taxes and fees
Reunion Resort - Near Theme Parks & Airport
Fridge, microwave, oven, stovetop

Bahama Bay, Davenport, Florida Oversize 2 Br condo

Bahama Bay, Davenport, Florida Oversize 2 Br condo
Bahama Bay
9.4 out of 10, Exceptional, (10 reviews)
"Spacious and clean unit. Quiet, clean and nice property overall (nice pool options and walking paths). Short drive to amenities and activities. Host was responsive."
United States
Holly
$236 nightly
The price is $261
May 26 - May 27
Total with taxes and fees
Bahama Bay, Davenport, Florida Oversize 2 Br condo
Pool

Disney 8mi~Heated Resort Pool~Hot Tub~Oasis

Disney 8mi~Heated Resort Pool~Hot Tub~Oasis
Kissimmee
9.4 out of 10, Exceptional, (3 reviews)
"The host was great and responsive. They handled every issue quickly and efficiently and communicated great and in a timely fashion. The location was quiet and felt safe. "
United States
Caleb C.
$350 nightly
The price is $368
May 21 - May 22
Total with taxes and fees
Disney 8mi~Heated Resort Pool~Hot Tub~Oasis
2 outdoor pools

Bahama Bay 515 Rum run unit 515

Bahama Bay 515 Rum run unit 515
2.0 star property
Bahama Bay
10.0 out of 10, Exceptional, (2 reviews)
"Place was exactly as described. The pool, amenities and restaurant are all top notch. It was a blessing and a privilege."
United States
wayne
$238 nightly
The price is $266
May 20 - May 21
Total with taxes and fees
Bahama Bay 515 Rum run unit 515
Outdoor pool, a heated pool

Disney Condo-Beautiful Lake views from XL Balcony

Disney Condo-Beautiful Lake views from XL Balcony
Orlando
9.6 out of 10, Exceptional, (40 reviews)
"Great place, location, and family friendly atmosphere. "
United States
Ethan
$246 nightly
The price is $273
May 22 - May 23
Total with taxes and fees
Disney Condo-Beautiful Lake views from XL Balcony
1 bedroom, in-room safe, desk, iron/ironing board

Sophisticated Retreat

Sophisticated Retreat
Kissimmee
9.4 out of 10, Exceptional, (10 reviews)
"Perfect for my wife and me. We were there for UDA College Dance championships. Super close and convenient to ESPN. Plenty of food options nearby. Facilities are good for the price point. Only issue is a heard of elephants lives above the unit. "
United States
Rocky C.
$173 nightly
The price is $194
May 20 - May 21
Total with taxes and fees
Sophisticated Retreat
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

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Clean room every day"
LINDA 3-night trip
Posted 2 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Find out more about Windermere

Windermere Condo Rentals information

Number of reviews
4,332
Accommodation
6112 Condo Rentals
Lowest Price
$117
Highest Price
$629

Frequently asked questions

How much do condos in Windermere cost?
You'll pay from $117 to $629 per night for condos in Windermere. No matter your budget, an epic stay is a click 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 condos in Windermere?
You can pick from multiple condos in Windermere with a total average guest review rating of 8.3. Vista Cay Commons By Ovh360 comes highly recommended if you're traveling with the kids or simply want extra space. This 3.5-star stay also features a swimming pool and individually decorated rooms. 3bd 2ba Condo Gold Rvc31032 B is another top option. It has a 4-star rating and amenities such as a swimming pool and express check-out services.
How many condos are there in Windermere?
Work out your vacation dates and then choose from 6112 condos in Windermere. For official business travel, a family getaway or anything in between, Expedia can help you find the perfect space in just a click or two.
What are the best cheap condos in Windermere?
With condos starting from just $117 per night, you may want to extend your visit to Windermere! One property that's easy on your finances is 3bed Lakeview Balcony Vista Cay. It comes with the space you need as well as a swimming pool and a lake view. Another favorite is 5024 Shoreway Loop #205 - 2 Bedroom Condo By Redawning, which offers a swimming pool and a barbecue grill. If you're sightseeing in Windermere and want to save money, there are lots of terrific free attractions to add to your itinerary. Universal CityWalk and Lake Bryan are always favorites. This price was 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.
Are there any family-friendly condos in Windermere?
Put your feet up at Vista Cay Commons By Ovh360, a 3.5-star option not far from downtown. Amenities here include individually decorated rooms and a swimming pool. Another family-friendly condo is 3bd 2ba Condo Gold Rvc31032 B. A swimming pool and WiFi help make this 4-star escape a traveler favorite. Windermere boasts an array of family-friendly attractions to discover that'll entertain the kids. Walt Disney World® Resort and Universal Studios Florida promise a fun day out for visitors of all ages.
Are there any 5-star condos in Windermere?
Unfortunately, there are no 5-star condos in Windermere. But you will find some terrific 4-star stays. Reserve your spot at 3bd 2ba Condo Gold Rvc31032 B, about 7 miles from downtown. A swimming pool and a balcony are a couple of the many conveniences here. 3bd 2ba Condo Gold Rvc30533 Bedroom Rhof is another upmarket option. It comes with a swimming pool and a balcony and is located around 7 miles from the center of Windermere.
Why book your condo in Windermere with Expedia?
Expedia makes it a breeze to find your dream condo in Windermere. Looking for a high-end stay? Take advantage of our filters to search for properties with a 5-star rating. If you have a set budget, choose how much you're willing to spend and then check out our fabulous deals. We'll help you find the perfect pad whatever your style of travel or plans.
How can I find cheap condos in Windermere?
Expedia can help you look for cheap condos in Windermere. To book the perfect stay in a couple of clicks, simply use our handy filter tool to refine your search results by amenities, budget and star rating.
What is there to do in Windermere near my condo?
The ultimate travel accessory is a well-planned itinerary. Isleworth Golf and Country Club is a top place to begin your exploration of Windermere.

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