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Condo vacation rentals in Winter Springs

Find and book unique condos on Airbnb

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Popular amenities for Winter Springs condo rentals

Weekly condo rentals

Superhost
Condo in Kissimmee
4.75 out of 5 average rating, 12 reviews

Mystic Dunes Golf Resort-2 bedroom weekly

MarcyRating, 5 stars76 months ago
The condo had everything we needed and the service was great. There were activities available throughout the week of a diverse variety. The location is just minutes away (no matter what time of day) from the Animal Kingdom back entrance where all of the parks can be accessed with minimal traffic. Brooke was very helpful in letting us know exactly what to do do when we arrived. I was extremely pleased with our experience and I can be a tough judge!
Guest favourite
Condo in Kissimmee
4.88 out of 5 average rating, 25 reviews

Beautiful Vacation Condo at Windsor Palms Resort

IvonneRating, 5 stars4 months ago
Very cozy apartment, clean, super-equipped kitchen, comfortable beds, showers with super hot water, very conveniently located to go to Disney and Universal parks
Top guest favourite
Condo in Orlando
4.92 out of 5 average rating, 109 reviews

P12# Vista Cay/ Walk to OCCC & New EPIC PARK !

AlanRating, 5 stars2 weeks ago
This was our second stay at Katharines and it was just as enjoyable. Love the location and the view over Lake Cay. Everything went smoothly on check-in. Plenty of restaurants within walking distance or a short drive away. Hope to be back in the future.
Superhost
Condo in Orlando
4.5 out of 5 average rating, 4 reviews

Kingstown Reef, FL, *1 Bedroom Deluxe #2

EricRating, 5 stars89 months ago
Nice and clean place to stay near Sea World!
Guest favourite
Condo in Kissimmee
4.9 out of 5 average rating, 220 reviews

Because you deserve it! Disney - Pool - Tiki Bar

NatashaRating, 5 stars3 weeks ago
Just a great place! Good location. Very clean and comfy! Right by the parks. Very hospitable and generous. Thankyou!
Guest favourite
Condo in Orlando
4.99 out of 5 average rating, 138 reviews

Serene Lakeview By DisneyWorld -Universal Stds 8mi

CarrieRating, 5 stars3 days ago
Adir's place was fantastic. There were many personal touches that made it feel more cozy, which I've found in Orlando can be a struggle. I loved how there were cozy blankets, bathrobes, and a few treats when we arrived. The location is awesome. Very close to anything you could need, Disney, Universal, and the airport. Dollar Tree, Starbucks, Dunkin, Chick-Fil-A, Walgreens, and many more places are all within walking distance. I loved how peaceful the condo and location felt, despite being surrounded by everything. The view was beautiful to wake up to and my kids enjoyed playing in the pool. We would definitely recommend and be happy to stay again!
Guest favourite
Condo in Ventura
4.9 out of 5 average rating, 10 reviews

Ventura Country Club Home away from home

HamidRating, 5 stars1 month ago
Excellent host, very responsive to our needs. Highly recommend.
Superhost
Condo in Kissimmee
4.88 out of 5 average rating, 114 reviews

2-104 Legacy Dunes, Lake View, Heated Pool, Gym

AlyssaRating, 5 stars6 months ago
This was my first experience with AirBnb and I’ll probably never go back to hotels. I had a great experience with Anthony. The house was clean, there were great amenities, and Anthony was very responsive and gave a lot of details so there was no confusion.

Pet-friendly condo rentals

Superhost
Condo in Four Corners
4.79 out of 5 average rating, 90 reviews

Disney 3BR |Suite Jacuzzi,Game Room,Resort |10 gts

MelissaRating, 5 stars1 week ago
The house is amazing, the view is incredible and it was spotless. I would go again no doubt.
Guest favourite
Condo in Orlando
4.96 out of 5 average rating, 47 reviews

London House | Orlando Airport Private Condo

LakenzieRating, 5 stars4 weeks ago
Enjoyed every moment in his apartment. Everything is nearby
Guest favourite
Condo in Kissimmee
4.87 out of 5 average rating, 391 reviews

Newly Renovated Condo near Disney!

CarmenRating, 5 stars5 days ago
This is a very nice and spacious condo with a great location near Disney World. Unit was spotless and very comfortable. Will stay here again if traveling in the area. Wonderful restaurant options and easy access to main highways. excellent location
Guest favourite
Condo in Kissimmee
4.93 out of 5 average rating, 124 reviews

Cozy single story condo near Disney

CindyRating, 5 stars1 month ago
very nice place. clean and had everything we needed for our time there.
Guest favourite
Condo in Davenport
4.79 out of 5 average rating, 39 reviews

Waterview 2BDR | 1st Floor | Near Disney | Pool

KevinRating, 5 stars2 weeks ago
I honestly couldn't have asked for a better place. It felt homey and more important for me, the environ was QUIET & PEACEFUL. The effort Dana has put into keeping it simple but effective resonated well with me and my family for our stay. Definitely my first choice if I'm back in the area and need a place.
Top guest favourite
Condo in Kissimmee
5 out of 5 average rating, 104 reviews

Bongos Disney Pad; First Floor Gated Resort Condo.

HollynRating, 5 stars2 weeks ago
We were so lucky to book Bongo’s Disney Pad for a week in April. My one year old was thrilled by all the toys and the place had everything we needed plus extra touches. Lina was super responsive and helpful, and the cleaner was immaculate. We can’t wait to come back!
Guest favourite
Condo in Orlando
4.87 out of 5 average rating, 143 reviews

403 - Near Universal, Disney - Convention Center

BrittanyRating, 5 stars3 weeks ago
Beautiful, clean, quiet and spacious condo. We would definitely stay again! We highly recommend staying here. Close proximity to everything.
Superhost
Condo in Kissimmee
4.85 out of 5 average rating, 110 reviews

Westgate Vaction Villas - 1 Bedroom

WillRating, 5 stars2 months ago
Eddie was extremely responsive, the place was “as advertised,” and our family enjoyed the stay.

Condo rentals with a pool

Guest favourite
Condo in Four Corners
4.87 out of 5 average rating, 148 reviews

LUXURY RESORT & GOLF CONDO MIN CLOSE TO DISNEY

HazelRating, 5 stars1 month ago
I love this place. The view was amazing. The host made me and my family feel so welcomed. The host checked on us everyday to make we were good and didn’t need anything. I really appreciate it
Guest favourite
Condo in Davenport
4.78 out of 5 average rating, 65 reviews

Lovely 1 Bedroom Apartment with Pool and Jacuzzi!

MalahkiRating, 5 stars3 weeks ago
We had a wonderful stay at Danny's home! It was incredibly comfortable and made us feel right at home. The amenities were fantastic, and the atmosphere was warm and inviting. Highly recommend!
Top guest favourite
Condo in Kissimmee
4.97 out of 5 average rating, 74 reviews

Family Friendly Condo Near Disney World

MoniqueRating, 5 stars4 months ago
Not only was Amanda an amazing host she also provided a space that was perfect for my family! The set up was great in the 2nd bedroom as it had a larger bed on the bottom and then a top bunk. The amenities in the complex were also great! We took advantage of the pool, basketball court, and even had a meal at the bar. Amanda was great with her communication and even checked in even though it was also Holiday time for her family! I would definitely recommend the stay due to its cleanliness and location and any place of Amanda’s I would stay in!
Top guest favourite
Condo in Kissimmee
4.94 out of 5 average rating, 32 reviews

Near Disney World | Resort w/ Pools

TomRating, 5 stars1 month ago
I stayed there for three months last winter so a warm pool and hot tub were essential. The 6 foot pool is heated to 83° to 85°. The hot tub to about 101°. It was a 15 minute Uber to Disney. The clubhouse has a convenience store, a 50 seat movie theater, pool table, ping-pong table, arcade and a bar that served sandwiches, pizza, chips, etc. Tuesday and Thursday mornings they served pancakes that were quite good. The beds were very comfortable as well as the entire condo. The kitchen was well equipped, with the exception of a full-size blender and a hand mixer. The owner always responded to my texts within a very short time. My kids are lobbying me to rent it again next winter because they liked it so much!
Guest favourite
Condo in Kissimmee
4.93 out of 5 average rating, 135 reviews

Chic Condo + Star Wars Room | Pool & Near Disney

SabrinaRating, 5 stars1 week ago
Kayla was a great host and I loved the condo immensely! Looking forward to visiting again.
Superhost
Condo in Kissimmee
4.84 out of 5 average rating, 137 reviews

Lovely 3-BR Condo With Pool 5.7mi from Disney!

GnanRating, 5 stars2 weeks ago
Great place. Thank you for hosting us. Overall a great stay and the kids had a great time.
Guest favourite
Condo in Kissimmee
4.91 out of 5 average rating, 11 reviews

Windsor Hills Condo Near Disney

JohnnyRating, 5 stars1 month ago
We enjoyed staying at this place! Travis described it perfectly and there was plenty of space for our family of 5 (3 kids 10, 7, 5). Pool was amazing with slides for the kids and most places were within 5-10 min drive. If you have kids and are doing Disney, don’t bother bringing a stroller. They have a double stroller that comfortably fit my kids (rotating seats). Excellent place and we will be back again in this condo!
Guest favourite
Condo in Kissimmee
4.9 out of 5 average rating, 48 reviews

Vacation Condo Resort

BenRating, 5 stars4 weeks ago
Very family-friendly with included amenities and easy drive to all the attractions. Includes access to the subdivision's great waterpark (slides, lazy-river, splashpad, pool, hot-tub, gym, bar). Also another pool adjacent to the building. Bright, spacious, and clean unit. Kitchen has everything necessary. Host is extremely responsive and attentive. Would definitely stay again.

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