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Compare 5853 Condo Rentals in Windermere with updated reviews, rates, and availability.

Pool
Cozy condo at the Magical City ORLANDO-FL 13 minutes from airport.
10.0 out of 10, Exceptional, (3)
"Everything was great we loved the house and would definitely go back."
Cozy condo at the Magical City ORLANDO-FL 13 minutes from airport.
Pool
Style, Luxury & Stunning Views, Star Wars
10.0 out of 10, Exceptional, (74)
"Loved everything about this rental; wouldn't change a thing!"
Style, Luxury & Stunning Views, Star Wars
Exterior
2-102 Legacy Dunes resort, Kissimmee, close to Walt Disney World, Heated Pool
10.0 out of 10, Exceptional, (15)
"It was a perfect base for our stay - location-wise it's pretty unbeatable in its proximity to DisneyWorld, and nestled as it is in a large, well-maintained and quiet gated complex (bigger than I realized) . I enjoyed waking to the sound of the fountain on the lake, and loved the pool area for its quiet (but a great playlist though!) and cleanliness. The condo itself was spotless and comfortable, and we particularly appreciated the two ensuites and the large closets. Only thing I would change is...
2-102 Legacy Dunes resort, Kissimmee, close to Walt Disney World, Heated Pool
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Pool
Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2
9.8 out of 10, Exceptional, (149)
"Such a lovely property. The 2 bedrooms were more than enough for our family of 4. Everything was exactly as described. Great location for the unit, central to both pools (neither of which was very busy) with a beautiful fountain/pond to overlook and enjoy while having morning coffee on the screened in patio. The gated complex is quiet and close to endless choices for dining/shopping. Easy drive to Disney. The owners are wonderful- can’t go wrong staying here."
The price is $95
$249 total
includes taxes & fees
Jun 14 - Jun 15
Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2
Outdoor pool, a heated pool
MEMORIAL DAY SALE 109+/N MAY 28-JUN 6 2.5 BDR 2BTH JETSKI LAKE SLEEP 8 1M DISNEY
9.8 out of 10, Exceptional, (136)
"Place was clean, spacious, amazing view from balcony and has everything you need. Will definitely stay here again!!"
The price is $109
$289 total
includes taxes & fees
May 28 - May 29
MEMORIAL DAY SALE 109+/N MAY 28-JUN 6 2.5 BDR 2BTH JETSKI LAKE SLEEP 8 1M DISNEY
Outdoor pool, a heated pool
3 miles to Disney, 1st Floor, Gated Resort, Roomy, Comfy & Quiet
9.8 out of 10, Exceptional, (100)
"We booked this stay with the idea in mind that we would be 4 adults and one child. But plans changed and only ended up being 2 adults and 1 child. The house is huge, very spacious. If you’re looking for a great place to relax after a busy day at the Disney parks this is the place for you. The hosts were very accommodating and friendly. Anna was nice enough to allow us an early check in of 12 noon, but we ended up being stock in some heavy traffic. The overall property was great. Heated salt...
3 miles to Disney, 1st Floor, Gated Resort, Roomy, Comfy & Quiet
Outdoor pool, a heated pool
Water Park & Fantastic Pool only Minutes To Walt Disney World's Front Gate!!!
9.8 out of 10, Exceptional, (188)
"Kevin was a superb host. He always answered immediately with questions and requests. He was always friendly and helpful. The condo was beautiful and clean. Better than we expected and just as pictured! The highchair was used and helpful for my 11 month old grandson. Everything we needed was at our fingertips, whether it was in the condo, the store there, or getting instacart orders. Our family thoroughly enjoyed the wonderful pool and small waterpark. It was great to be able to get well cooked...
Water Park & Fantastic Pool only Minutes To Walt Disney World's Front Gate!!!
Pool | A heated pool
Beautiful - Luxury Condo! Top Resort! 3 Miles From Disney! Get More For Your $$$
9.8 out of 10, Exceptional, (134)
"Very nice condo, nice property, easy access to Disney, Universal, and interstates, would stay there again."
Beautiful - Luxury Condo! Top Resort! 3 Miles From Disney! Get More For Your $$$
Exterior
Caribbean Villa
9.8 out of 10, Exceptional, (12)
"Stay was nice, close to stores and easy drive to Disney. Would stay again."
The price is $85
$226 total
includes taxes & fees
May 22 - May 23
Caribbean Villa
Fridge, microwave, oven, stovetop
ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
9.8 out of 10, Exceptional, (67)
"It was a special weekend with old friends and we couldn't have picked a better place to stay. The location is very convenient, the apartment is clean and spacious, and we thoroughly enjoyed the breeze sitting on the screened in porch. The view of the moss lined trees overlooking the blooming lily pads in the pond was picture perfect. I cant say enough good things about the gracious host. She was responsive and professional. The beds were as comfortable as could be and the apartment was nicely...
The price is $149
$419 total
includes taxes & fees
May 22 - May 23
ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
Pool
Top Floor Oversize Balcony, Premium Inclusive Resort Amenities
9.8 out of 10, Exceptional, (18)
"Beautiful condo"
The price is $236
$391 total
includes taxes & fees
May 22 - May 23
Top Floor Oversize Balcony, Premium Inclusive Resort Amenities
Property grounds
Luxury Condo at Hotel prices at Lake Cay, Orlando Fl
9.8 out of 10, Exceptional, (124)
"Really enjoyed this property. Check in was easy and access to the community was also simple. Unit was clean and comfortable. Overlooks a lake with an alligator and a nice view of sea world. I would stay here again without a doubt."
Luxury Condo at Hotel prices at Lake Cay, Orlando Fl
Outdoor pool, a heated pool
Paradise Dunn Right! Home away from Home at Tuscana!
9.6 out of 10, Exceptional, (66)
"Would definitely stay here again!"
Paradise Dunn Right! Home away from Home at Tuscana!
Property grounds
2 Bedroom /2 Bathroom Condo near Disney-Balcony-EV Charging-Free Parking
9.6 out of 10, Exceptional, (4)
"Everything was perfect"
2 Bedroom /2 Bathroom Condo near Disney-Balcony-EV Charging-Free Parking
Game room
Bahama Bay Resort Unit 28703 - 3BR 2BA Ground Floor Condo - Great Value
9.6 out of 10, Exceptional, (146)
"Family vacation with grandkids. Loved everything about the resort. Enjoyed all the amenties and our unit was perfect. Friendly staff and beautiful grounds. Would return and recommend"
Bahama Bay Resort Unit 28703 - 3BR 2BA Ground Floor Condo - Great Value
Outdoor pool, a heated pool
Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER
9.6 out of 10, Exceptional, (88)
"Stayed with 3 colleagues for a trade show at the OCC."
Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER
View from property
3121 308 - 3 Bedroom Corner Condo Overlooking Pond in Storey Lake Resort
9.6 out of 10, Exceptional, (18)
"The location is great (close to Disney), and the property is very well taken care of. Lots of amenities for the whole family to enjoy :)"
3121 308 - 3 Bedroom Corner Condo Overlooking Pond in Storey Lake Resort
Pool
Neat & Cozy Pool View Condo -8 min from Disney
9.6 out of 10, Exceptional, (14)
"Property was in a perfect location & the amenities of the property were just what was needed. Thank you!!"
Neat & Cozy Pool View Condo -8 min from Disney
Outdoor pool, a heated pool
Lake Buena vista resort- 5 min to disney!
9.6 out of 10, Exceptional, (53)
"Property was clean, had everything you could need. Sergio was very kind and quick to reply when texted. Close to the parks and a Publix right down the street. Everything we needed."
Lake Buena vista resort- 5 min to disney!
Exterior
Windsor Hills 3 bed condo close to pool and water park, just 2 miles from Disney
9.4 out of 10, Exceptional, (127)
"Apartment couldn’t be in a better location with a Super Walmart just 2 min away with gas station and other restaurant and business just a few miles on 192. About 10min from Disney it was a perfect place to stay. The apartment has everything you would need for a Disney stay, it even has a high chair which was perfect for our 18month old."
Windsor Hills 3 bed condo close to pool and water park, just 2 miles from Disney
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See all available properties in Windermere
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.

Other property types in Windermere

Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4839)
"Great hotel directly in airport "
The price is $189
$213 total
includes taxes & fees
May 29 - May 30
Hyatt Regency Orlando International Airport
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas
Lake Buena Vista Resort Village & Spa
4.0 star property
8.4 out of 10, Very Good, (7214)
"Amazing "
The price is $144
$188 total
includes taxes & fees
May 22 - May 23
Lake Buena Vista Resort Village & Spa
Outdoor pool, pool umbrellas, sun loungers
Avanti International Resort
3.0 star property
7.8 out of 10, Good, (2085)
"Always stay at Avanti …Great time "
The price is $76
$102 total
includes taxes & fees
Jun 6 - Jun 7
Avanti International Resort
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.

Windermere Condo Rentals information

Number of reviews
2,896
Accommodation
5853 Condo Rentals
Lowest Price
$85
Highest Price
$236

Frequently asked questions

How much do condos in Windermere cost?
You’ll pay from $85 to $236 per night for condos in Windermere. Whatever your budget, a terrific stay is a click away on Expedia. 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.
What are the best condos in Windermere?
There are multiple condos in Windermere with a total average guest review rating of 9.4. Vista Cay Commons By Ovh360 comes highly recommended if you’re traveling with the kids or you just want to spread out. This 3.5-star property also offers premium bedding and a swimming pool. 3bd 2ba Condo Gold Rvc31032 B is another popular option. It has a 4-star rating and amenities such as a swimming pool and free self parking.
How many condos are there in Windermere?
Pack your bags and choose from 5853 condos in Windermere. For a work-related trip, a getaway with friends or anything in between, Expedia will help you find an ideal stay in a few simple clicks.
Are there any family-friendly condos in Windermere?
Vacationing with the family in Windermere is easy at Vista Cay Commons By Ovh360. With amenities such as a washer and dryer and a children’s pool, your crew will enjoy their space at this 3.5-star stay. 4114 Breakview Dr 307 2 Bedroom Condo By Redawning is another family-friendly condo. It has a 4-star rating and amenities including a swimming pool and a dishwasher. After checking in and chilling together in your comfy new digs, it’s time to start exploring. Walt Disney World® Resort and Universal Studios Florida are some of the best family-friendly attractions in Windermere.
Are there any 5-star condos in Windermere?
Windermere doesn’t have any 5-star condos — but you and the crew can still stay here in style! Why not try 3bd 2ba Condo Gold Rvc31032 B? Located approximately 7 mi from the downtown area, this 4-star option offers a swimming pool and a separate dining area. 3bd 2ba Condo Gold Rvc30533 Bedroom Rhof is another fantastic pick just 7 mi from the center of Windermere. Also holding a 4-star rating, it features amenities such as a swimming pool and a separate dining area.
Why book your condo in Windermere with Expedia?
Booking a condo in Windermere is as easy as entering your travel dates and choosing an option that meets your requirements. On the search for something luxurious or low cost, or a property that also has a kitchen? Use Expedia’s search filters to narrow your results even further and find your ideal match.
How can I find cheap condos in Windermere?
Expedia can help you narrow your search for cheap condos in Windermere. To find your dream stay in a couple of quick clicks, 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?
You’ll find tons of fabulous things to fill your itinerary with in Windermere. Make tracks to leading attractions like Walt Disney World® Resort, Universal Orlando Resort and Magic Kingdom® Park. Epcot®, Universal’s Islands of Adventure and Discovery Cove are other must-see’s.

Recent reviews of Windermere hotels
Expedia verified reviews

Caribe Royale Orlando

Caribe Royale Orlando

5/5 Excellent
Clean an updated room
"Nice updated room but oddly the door was a couple of inches or so too short and light beamed in. Can clearly hear the conversation of anyone standing by the door talking; such as the neighboring rooms. Wasn’t much of an issue since we didn’t sleep in the sitting area & the other guests were never there long. Unfortunately, the waterfall at the pool didn’t not work and the dj had only one beat. My young adult children thought the dj was terrible and would have preferred a playlist/radio. Overall the staff was nice and accommodating, the hotel was clean, and the breakfast restaurant was great."
A verified traveler stayed at Caribe Royale Orlando
Posted 16 hours ago
Caribe Royale Orlando