Condo holiday rentals in Winter Springs

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Popular amenities for Winter Springs condo rentals

Weekly condo rentals

Top Guest favourite
Condo in Orlando
5 out of 5 average rating, 54 reviews

Classy Disney Themed Condo with FREE shuttle!

SannaRating, 5 stars1 day ago
We enjoyed our stay! The place short driving distance from Magic Kingdom and it was easy to get in and out. The place was also very clean and full of Disney themed items. Loved it!
Guest favourite
Condo in Kissimmee
4.91 out of 5 average rating, 78 reviews

Coastal Retreat | 15 min to Disney

MakaylaRating, 5 starstoday
Ana’s place was very comfortable and welcoming! We felt right at home during our vacation, and the check in and out process was very easy and accessible. VERY clean, and that added to our experience all the more. Very close to Walt Disney World which was a plus! We’re very happy with our stay and would stay here again.
Superhost
Condo in Orlando
4.84 out of 5 average rating, 50 reviews

Lovely 2/2 Thorton Park Condo w/ secure parking

MaryannRating, 5 stars2 months ago
Beautiful place! Clean & very spacious! Definitely worth it,book here again!
Guest favourite
Condo in Orlando
4.92 out of 5 average rating, 101 reviews

Location,Location 3bd 2bth near parks conv.ct/Int.

LucindaRating, 5 stars4 days ago
Working with Isabela, was easy. The place was perfect for our needs. Beautiful, easy access to local attractions. Would highly recommend.
Guest favourite
Condo in Orlando
4.86 out of 5 average rating, 73 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

kaitlyn Rating, 5 stars6 days ago
very good communication and was a great stay
Guest favourite
Condo in Kissimmee
4.93 out of 5 average rating, 82 reviews

Modern, spacious, and relaxing!

JonRating, 5 stars1 week ago
Great place to stay with a family, great location, lots of amenities, great ability to use all three pools on the properties. The layout of rooms and bathrooms were nice and adequate . Lower level condo with some noise from above condo. Overall a great stay!
Guest favourite
Condo in Orlando
4.97 out of 5 average rating, 93 reviews

Modern Lake view Condo 1 mile from Disney

AniaRating, 5 stars1 week ago
A wonderful stay in Orlando beautiful view and the condo is super clean and cozy me and my boyfriend enjoyed our stay and it was in the perfect area plenty of dinner spots and fun activities close by you will love this place and I will make sure to book again my next visit to Orlando
Superhost
Condo in Florida Center
4.85 out of 5 average rating, 82 reviews

#2608 Lakeview Luxury Condo by I-Drive/Universal

CharlesRating, 5 stars2 weeks ago
The stay was amazing. Very peaceful community and very nice staff

Pet-friendly condo rentals

Top Guest favourite
Condo in Davenport
4.94 out of 5 average rating, 120 reviews

9 miles from Disney - Bella Piazza spacious condo

PabloRating, 5 stars4 days ago
Quiet and beautiful area just 20 minutes driving to the Disney parks. Very spacious inside, comfortable after a whole day of walking in the sun! Will be staying again for next Disney visit.
Guest favourite
Condo in Orlando
4.95 out of 5 average rating, 127 reviews

Vista Cay Luxury Vision Walk to EPIC and OCCC

ReneeRating, 5 stars2 weeks ago
Great place to stay and certainly a great price for what you get .
Guest favourite
Condo in Kissimmee
4.94 out of 5 average rating, 117 reviews

3 Bedroom w/large patio on Resort Golf Course

PhillipRating, 5 stars2 weeks ago
We definitely enjoyed our stay and maybe some time in the near future, we will return.....
Superhost
Condo in Kissimmee
4.76 out of 5 average rating, 254 reviews

King Bed Small Studio Disney World Universal

CourtneyRating, 5 stars2 weeks ago
Laura’s place was wonderful for my husband and I. It was our first time to Kissimmee. It is a very short distance from the parks and attractions. It was also close to quality restaurants and convenient gas stations. Laura’s studio was clean and represented what was expected from the photos. This is a very cozy location with pool and hot tub. Laundry and snacks were easily accessible. Overall, it was a wonderful stay and the price was in our budget!
Superhost
Condo in Davenport
4.79 out of 5 average rating, 234 reviews

Brand New AwardWinning Renovated Condo Near Disney

AntoinetteRating, 5 stars2 weeks ago
Cai Ling and John were amazing hosts! Their place was clean and in a great location. Hope to be back soon!
Guest favourite
Condo in Kissimmee
4.91 out of 5 average rating, 108 reviews

Home away from home for the Parks!

AndreaRating, 5 stars5 days ago
Our stay with Renzo and Carolina was very pleasant. They are super friendly and incredibly attentive hosts, always making sure we were comfortable. They even asked us in advance what temperature we preferred in the house, and when we arrived, everything was set just the way we requested. The house was spotless, very well maintained, and located in a nice, quiet, and central area. We truly enjoyed our time there, and without a doubt, we’ll be happy to stay here again next time we come back. Thank you so much for everything!
Guest favourite
Condo in Orlando
4.91 out of 5 average rating, 149 reviews

Amazing Clean Studio near Conventions & Disney

SiennaRating, 5 stars2 weeks ago
Dan was very responsive and answered all my questions and was very friendly and accommodating. Space was perfect for me my husband and our dog . Great location Ubers in the area were cheap and there was lots to do.
Superhost
Condo in Kissimmee
4.81 out of 5 average rating, 202 reviews

Family Friendly I Mins from Disney I Resort Pool

JamyrahRating, 5 stars3 weeks ago
Overall my stay here was good. The Airbnb was clean, instructions were clear on getting inside, not a noisy area except the neighbors above the 2 bed room were noisy at night. I made use of the washer and dryer using the complimentary laundry detergent pods left out for use, I made use of the iron/ironing board, and I made use of the tv in the bedroom. I didn’t have any concerns or trouble so I didn’t need to contact Andres, but he reached out the day after checking in to make sure everything went smoothly. The only thing I’d like to share as a heads up is that the gate to get into the apartment complex only allows one car at a time so there were times where after getting approved to go through, a car would turn in and go through before we could and so we’d have to reverse and get approved again so that the gate barrier arm would go up again.

Condo rentals with a pool

Guest favourite
Condo in Kissimmee
4.96 out of 5 average rating, 75 reviews

Resort Style Sunshine Oasis near Theme Parks

AmyRating, 5 stars3 weeks ago
LaBrina - thank you so much for the awesome stay!! Despite checking in so late, LaBrina was super responsive in ensuring we had a smooth check in which I really appreciated. Place was as described - great location, esp if you are there to visit Disney/Universal. Lots of good restaurants and shops in the areas Slight downside were we noticed some stains on the beds / towels but Airbnb had a great laundry system. Floors, kitchen and bathroom were clean. Overall great stay and value - would come again. Would’ve loved to taken advantage of the amenities more. Great host. Great place :)
Guest favourite
Condo in Kissimmee
4.95 out of 5 average rating, 37 reviews

Peaceful lake view escape

CollinRating, 5 stars1 month ago
Loved loved loved this location. Very close to Disney. Location was very clean and cozy. Maria was very accommodating and flexible with check in. Beautiful view from balcony and the most comfortable bed I’ve slept on in a while. The only hesitation is that it is on the 3rd floor with no elevator. So if you’re handicap or unable to walk up stairs, this might not be the spot for you. But the condo is beautiful and comfortable.
Top Guest favourite
Condo in Orlando
5 out of 5 average rating, 13 reviews

King Studio w/ Balcony | Near Theme Parks

BethanyRating, 5 stars2 weeks ago
I cannot recommend these hosts enough! Not only were they extremely proactive and communicative for all of my questions and helping me with the check-in process before I booked, they also sent me everything I needed to know after the booking and we’re extremely helpful before I checked in and after. I will definitely be booking through them again. It is one of my best experiences on Airbnb so far!
Guest favourite
Condo in Kissimmee
4.79 out of 5 average rating, 187 reviews

Mickey's Retreat(K2)

JackRating, 5 stars1 month ago
Stayed at Celso’s apartment for 2-weeks. It was a great size for 2 people and an ideal location for those looking to do the Disney and Universal parks. Apartment is just a short drive away from plenty of shops, restaurants and fast food places. It also has a 24h petrol (gas) station just outside of the complex which is really convenient. Overall, really enjoyed our stay the complex is really nice and feels very welcoming. Would highly recommend for two people. Celso was a great host, super responsive to any messages and helpful with any questions we had during our stay. One minor downside, not to the fault of Celso or his apartment, but the complex had a nesting hawk during our stay. This was no issue for 95% of our stay, but did swoop at us once. Would advise being cautious when walking to the car park, especially with young children.
Top Guest favourite
Condo in Orlando
5 out of 5 average rating, 9 reviews

Stunning waterfront Views, 1 mile to Disney 2 bath

JayneeRating, 5 stars2 days ago
We were there for a volleyball tourney at the OCCC and it was a great location. Plenty of places to walk to or close driving distance. We also went to Magic Kingdom and Animal Kingdom and it was a good drive to both locations. The pool area was nice - although we didn’t get to really enjoy it because we were at the tourney. We would highly recommend and would book again if in the area. Hosts were very responsive and made sure we had everything we needed.
Top Guest favourite
Condo in Kissimmee
4.97 out of 5 average rating, 32 reviews

Mickey & Star Wars 3bed Condo close to Disney!

RaelynRating, 5 stars2 weeks ago
Great value, great location. The unit was very clean and nicely decorated, without clutter. Pool was wonderful. Jesus was very responsive when we messaged him. We would definitely stay here again
Top Guest favourite
Condo in Davenport
5 out of 5 average rating, 8 reviews

Stunning 3BR Condo Near Disney

WanisaRating, 5 stars6 days ago
I loved that this place is gated so I get very safe. We picked this place because we wanted to be in the middle of LegoLand and DisneyWorld. It was so clean and we spent time at the resort pools which I really appreciate because it was so hot.
Guest favourite
Condo in Kissimmee
4.85 out of 5 average rating, 68 reviews

Disney Retreat

JackRating, 5 stars2 weeks ago
Had a few small issues while we were staying but got an answer usually within an hour with solutions and check ups to make sure everything was good. Cannot fault it as it was close enough to everything we wanted to do, but far enough away that it was nice and quiet. The pool was very nice and we regularly had it to ourselves. Would happily stay again when we come back.

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