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Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Windermere condo rentals

Aerial view
Vacation Village Orlando, Celebration

Condo in Kissimmee

Vacation Village Orlando, Celebration
3.0 star property
8.6 out of 10, Excellent, (3119)
"Great place to stay"
United States
Jose
$133 nightly
The price is $150
Jan 11 - Jan 12, 2026
Total with taxes and fees
Vacation Village Orlando, Celebration
Exterior
Disney & Universal Condo Grand Opening Specials! Amazing Views, Spacious 2B 2BA

Condo in Orlando

Disney & Universal Condo Grand Opening Specials! Amazing Views, Spacious 2B 2BA
2.0 star property
10.0 out of 10, Exceptional, (1)
"Truly an incredible space"
United States
Sean Parker S.
Disney & Universal Condo Grand Opening Specials! Amazing Views, Spacious 2B 2BA
Interior
BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️

Condo in Kissimmee

BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️
10.0 out of 10, Exceptional, (12)
"Enjoyed everything!"
United States
Caroline W.
$259 nightly
The price is $289
Jan 5 - Jan 6, 2026
Total with taxes and fees
BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️
2 bedrooms, iron/ironing board, WiFi, bed sheets
2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access

Condo in Vacation Village

2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access
10.0 out of 10, Exceptional, (4)
"Excellent host, very clean, coffee bar, and access to great facilities. Would highly recommend this place."
United States
Jodi
$244 nightly
The price is $268
Jan 14 - Jan 15, 2026
Total with taxes and fees
2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access
Children's area
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Condo in Kissimmee

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
9.2 out of 10, Wonderful, (149)
"Great place! Close to everything we wanted to do, hosts were easy to communicate with, place was clean and the community felt safe and secure as a woman traveling with her kiddo. I would absolutely stay again!"
United States
Hope M.
$180 nightly
The price is $202
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Fridge, microwave, oven, stovetop
Warm and cozy 1 bed/1 bath Condo Just 7 miles from Disney!

Condo in Kissimmee

Warm and cozy 1 bed/1 bath Condo Just 7 miles from Disney!
9.4 out of 10, Exceptional, (81)
"Condo was perfect. Would stay again "
United States
Lori S.
$209 nightly
The price is $234
Jan 3 - Jan 4, 2026
Total with taxes and fees
Warm and cozy 1 bed/1 bath Condo Just 7 miles from Disney!
Pool
2bd/2ba condo close to Disney, Storey Lake

Condo in Kissimmee

2bd/2ba condo close to Disney, Storey Lake
10.0 out of 10, Exceptional, (5)
"It was an nice smooth experience renting out the property the pictures the were posted up on vrbo about the condo is exactly how the room is 10/10 experience"
United States
Luis C.
$270 nightly
The price is $301
Jan 6 - Jan 7, 2026
Total with taxes and fees
2bd/2ba condo close to Disney, Storey Lake
Pool
Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2

Condo in Kissimmee

Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2
9.6 out of 10, Exceptional, (193)
"We absolutely LOVED staying here for our vacation! The master bed is so comfy, and everything looks just like the pictures. We loved being able to relax in the pool after long days outside. I would definitely stay here again, thank you!!"
United States
Kristi C.
$218 nightly
The price is $244
Dec 28 - Dec 29
Total with taxes and fees
Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2
Fridge, microwave, oven, stovetop
Lake Eola view 1 bedroom Thornton Park

Condo in South Eola

Lake Eola view 1 bedroom Thornton Park
9.8 out of 10, Exceptional, (10)
"The location is exactly what I wanted without breaking the bank. The host was very informative and quick to respond. I will stay here again. "
United States
Judy G.
$142 nightly
The price is $157
Jan 1 - Jan 2, 2026
Total with taxes and fees
Lake Eola view 1 bedroom Thornton Park
Fridge, microwave, oven, stovetop
Renovated Condo Lake Eola View Great Location

Condo in South Eola

Renovated Condo Lake Eola View Great Location
10.0 out of 10, Exceptional, (10)
"It was a great stay in a great area with an amazing view! "
United States
Valerie
$151 nightly
The price is $167
Jan 4 - Jan 5, 2026
Total with taxes and fees
Renovated Condo Lake Eola View Great Location
Exterior
Luxe King Suite Bliss Getaway Condo Near Disney

Condo in Kissimmee

Luxe King Suite Bliss Getaway Condo Near Disney
9.6 out of 10, Exceptional, (27)
"Attractive place. "
United States
Kathryn B.
$137 nightly
The price is $153
Jan 11 - Jan 12, 2026
Total with taxes and fees
Luxe King Suite Bliss Getaway Condo Near Disney
Pool
Beautiful 1st Floor Condo in Gated Cane Island, Close to Parks

Condo in Kissimmee

Beautiful 1st Floor Condo in Gated Cane Island, Close to Parks
9.4 out of 10, Exceptional, (19)
"Spacious unit, great proximity to the parks. Close to stores and restaurants. "
United States
Erika D.
$351 nightly
The price is $379
Dec 30 - Dec 31
Total with taxes and fees
Beautiful 1st Floor Condo in Gated Cane Island, Close to Parks
Living area
Newly Remodeled! Condo in Center of all the Action!

Condo in Florida Center

Newly Remodeled! Condo in Center of all the Action!
8.8 out of 10, Excellent, (13)
"It wS straight to the ponit introduction were very clear the stay was easy and unbelievable wonderful very homie we organized put together i would definitely go back again "
United States
Von W.
$207 nightly
The price is $230
Dec 29 - Dec 30
Total with taxes and fees
Newly Remodeled! Condo in Center of all the Action!
Outdoor pool, a heated pool
Near Disney/Resort Pool, Bar & Gym

Condo in Champions Gate

Near Disney/Resort Pool, Bar & Gym
9.2 out of 10, Wonderful, (5)
"The property was great.. very clean and relaxing"
Canada
Dawn D.
$235 nightly
The price is $263
Jan 19 - Jan 20, 2026
Total with taxes and fees
Near Disney/Resort Pool, Bar & Gym
Exterior
Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER

Condo in Orlando

Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER
9.6 out of 10, Exceptional, (145)
"Great place. "
United States
Jeff D.
$454 nightly
The price is $504
Jan 10 - Jan 11, 2026
Total with taxes and fees
Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER
Fridge, microwave, oven, stovetop
Reunion Resort - Near Theme Parks & Airport

Condo in Reunion

Reunion Resort - Near Theme Parks & Airport
9.6 out of 10, Exceptional, (51)
"This was a beautiful property with all the amentities and space. "
United States
Derica N.
$329 nightly
The price is $367
Jan 2 - Jan 3, 2026
Total with taxes and fees
Reunion Resort - Near Theme Parks & Airport
Pool
Upstay - Condo w Pool and More - Near Disney

Condo in Winter Garden

Upstay - Condo w Pool and More - Near Disney
9.0 out of 10, Wonderful, (22)
"Great place! Convenient, cozy and clean!"
United States
SHARLA B.
$253 nightly
The price is $284
Jan 7 - Jan 8, 2026
Total with taxes and fees
Upstay - Condo w Pool and More - Near Disney
Pool
Buena Vista Resort Condo w/ Pool & Private Patio

Condo in Orlando

Buena Vista Resort Condo w/ Pool & Private Patio
8.6 out of 10, Excellent, (14)
"Condo was as advertised clean and close to everything. Would highly recommend this property for any Disney vacation."
Canada
Derek M.
$245 nightly
The price is $274
Jan 13 - Jan 14, 2026
Total with taxes and fees
Buena Vista Resort Condo w/ Pool & Private Patio
Outdoor dining
Sophisticated Retreat

Condo in Kissimmee

Sophisticated Retreat
9.4 out of 10, Exceptional, (6)
"Amazing! I will be staying here again!"
United States
MikeD
$173 nightly
The price is $194
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sophisticated Retreat
Pool
Upstay Champions Gate Home w Private Pool & BBQ

Condo in Davenport

Upstay Champions Gate Home w Private Pool & BBQ
2.0 star property
9.2 out of 10, Wonderful, (7)
"It is a beautiful house, very clean, with all its comforts, 100% recommended. ❤️"
United States
Ana C.
$330 nightly
The price is $369
Jan 11 - Jan 12, 2026
Total with taxes and fees
Upstay Champions Gate Home w Private Pool & BBQ
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

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Clean room, quiet hotel rooms"
Daniel 4-night trip
Posted 2 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Find out more about Windermere

Windermere Condo Rentals information

Number of reviews
3,811
Accommodation
5831 Condo Rentals
Lowest Price
$150
Highest Price
$504

Frequently asked questions

How much do condos in Windermere cost?
You'll pay from $150 to $504 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 9.3. 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 5831 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 $150 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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