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Apartment holiday rentals in Winter Park

Find and book unique apartments on Airbnb

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Popular amenities for Winter Park apartment rentals

Weekly apartment rentals

Top guest favourite
Apartment in Kissimmee
5 out of 5 average rating, 6 reviews

4731-103 Stay Magical • 2BR with Mickey Room & Mor

KaylanRating, 5 stars2 weeks ago
I have booked many air bnbs but this by far as been the best location & host. Rafaela did a great job at making me and my family feel welcomed and was very attentive to any questions that came about during our stay. We were provided with all house essentials making it feel exactly like home. Beautiful & clean place!
Guest favourite
Apartment in Orlando
4.86 out of 5 average rating, 71 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

AndreaRating, 5 stars6 days ago
This was at a very convenient location and very clean! Just as described and owner was very responsive!!! Very positive experience!
Top guest favourite
Apartment in Orlando
4.95 out of 5 average rating, 86 reviews

Penthouse Lakeview Minutes to Disney/ Universal

ScottRating, 5 stars3 weeks ago
The view was amazing! Enjoyed the home and the on-site pool… Jeff was very welcoming and I felt right at home staying here. Very close to many attractions in the Orlando area.
Guest favourite
Apartment in Florida Center
5 out of 5 average rating, 50 reviews

Boho Retreat: 7 min to Universal & Epic!

LexiRating, 5 stars1 day ago
My boyfriend and i desperately needed a vacation so i booked here! Absolutely loved how cozy and at home we felt, everything was nice and clean it felt like a home and oh my gosh the bed and pillows were literally the comfiest i’ve ever felt before! needless to say this was definitely the perfect place we could’ve chose to stay, we came home today feeling so refreshed and relaxed. Lais was very friendly and responded very quickly! I definitely recommend!
Top guest favourite
Apartment in Lake Buena Vista
4.94 out of 5 average rating, 63 reviews

Grand Villas Resort 2 bedrooms

KristenRating, 5 stars1 month ago
This was a great option for our family during our Disney visit. Great location and an easy drive to parks and attractions. It was super clean and the resort was amazing with lots of different activities during the week. The front desk checked in often and were super helpful. We will definitely choose here to stay for our next Florida trip.
Guest favourite
Apartment in Orlando
5 out of 5 average rating, 8 reviews

Stunning waterfront Views, 1 mile to Disney 2 bath

MadhukarRating, 5 stars1 week ago
We had a fantastic five-day stay! Check-in was smooth, even at 1:30 AM, which was greatly appreciated. The location is stunning—right next to a peaceful lake, making for a relaxing retreat. The house itself was charming and well-kept. While a few small details could be improved, they didn’t impact our overall experience. Water bottles weren’t provided upon late-night arrival, and bathroom amenities were minimal for a five-day stay. The kitchen lacked paper towels, only one toilet roll was available, and bath towels had some wear. The community pool wasn’t clean, possibly due to windy weather, so we skipped it. Despite these minor things, the beautiful setting and comfortable stay made this a wonderful trip. With small tweaks, it would be perfect. Highly recommend for a tranquil lake getaway!
Superhost
Apartment in Florida Center
4.85 out of 5 average rating, 81 reviews

#2608 Lakeview Luxury Condo by I-Drive/Universal

KayloRating, 5 stars2 weeks ago
Very easy to check in. Host was very communicative and helpful. The apartment itself was very clean and close to many attractions and restaurants.
Guest favourite
Apartment in Central Business District
4.93 out of 5 average rating, 30 reviews

FL King Velvet Suite- 3bdrm/2Bath-2000 sq ft

VanessaRating, 5 stars3 weeks ago
GREAT SPOT! In the heart of Lake Eola District and what a beautiful place with allllllll the views and windows to enjoy :) would book again in a heartbeat

Pet-friendly apartment rentals

Guest favourite
Apartment in Orlando
4.95 out of 5 average rating, 126 reviews

Vista Cay Luxury Vision Walk to EPIC and OCCC

ReneeRating, 5 stars1 week ago
Great place to stay and certainly a great price for what you get .
Guest favourite
Apartment in Kissimmee
4.94 out of 5 average rating, 116 reviews

3 Bedroom w/large patio on Resort Golf Course

JeannaRating, 5 stars1 month ago
The villa was absolutely amazing, better than the pictures. The house was super spacious for all 5 adults. Shuttle to the parks was convenient and on time. Host gave us a schedule to help navigate. Each bedroom has its own full bathroom. Living room was large and comfortable. Loved relaxing on the back patio overlooking the golf course. Host were on top of everything and made our stay absolutely perfect!
Superhost
Apartment in Davenport
4.79 out of 5 average rating, 233 reviews

Brand New AwardWinning Renovated Condo Near Disney

JasonRating, 5 stars2 weeks ago
Loved the condo and the resort. Will definitely rent again when we return to Orlando.
Guest favourite
Apartment in Orlando
4.99 out of 5 average rating, 138 reviews

Serene Lakeview By DisneyWorld -Universal Stds 8mi

CarrieRating, 5 stars1 month 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
Apartment in Celebration
4.9 out of 5 average rating, 111 reviews

Pet Friendly in Orlando Area near Disney.

TaylorRating, 5 stars1 month ago
This exceeding any expectations for taking our kids to Disney for the first time. Eric truly thought of everything to make the condo feel like home away from home and anything you need down to silverware for your our baby and toddler. This was such an exceptional experience and the resort was so much fun for our 1 year old and 3 year old!
Guest favourite
Apartment in Kissimmee
4.92 out of 5 average rating, 126 reviews

Cozy single story condo near Disney

KartikayeRating, 5 stars1 month ago
I had an absolutely fantastic experience staying at this Airbnb! The place was exactly as described - clean, comfortable, and beautifully decorated. Omar and Lucy were incredibly welcoming and responsive, ensuring we had everything we needed for a smooth stay. The location was perfect, close to great restaurants, shops, and public transport. I especially appreciated the small touches like fresh towels, a well-stocked kitchen, and fast Wi-Fi. I would definitely book this place again and recommend it to anyone visiting the area!
Superhost
Apartment in Four Corners
4.71 out of 5 average rating, 118 reviews

No BNB fees -Oasis Condo 5 min to Disney

Hannah RoseRating, 5 stars2 weeks ago
Great space! Perfect for our trip! Loved it was a gated area!
Guest favourite
Apartment in Orlando
4.9 out of 5 average rating, 146 reviews

Amazing Clean Studio near Conventions & Disney

KaterineRating, 5 stars1 month ago
enjoyed staying here , everything was very clean , smooth check in (and out) , comfortable bed !! loved everything

Apartment rentals with a pool

Guest favourite
Apartment in Kissimmee
4.91 out of 5 average rating, 77 reviews

Coastal Retreat | 15 min to Disney

StacyRating, 5 stars2 months ago
Perfect size for a small family. The pool also great!
Top guest favourite
Apartment in Orlando
5 out of 5 average rating, 52 reviews

Classy Disney Themed Condo with FREE shuttle!

LoriRating, 5 stars3 weeks ago
Shellie has really gone above and beyond with her condo! There were so many nice touches. Shellie really thought of everything! The beds were very comfortable. My friend and I felt very relaxed. The resort itself is clean, with a nice pool, exercise room, arcade. I even saw that they had stroller rentals. The shuttle that serves the resort takes a little while, but not bad for free. It picked us right up at the lobby.
Top guest favourite
Apartment in Orlando
4.92 out of 5 average rating, 103 reviews

Waterfront Condo minutes from Disney & Universal

CharleneRating, 5 stars2 weeks ago
Great location. Very comfortable and well maintained. Would stay here again. Ryan was very helpful with all my questions.
Superhost
Apartment in Orlando
4.86 out of 5 average rating, 116 reviews

Marriott Grande Vista Luxury Studio-like

LuzRating, 5 stars1 week ago
Robert , wow! Our stay was amazing. 100% recommend. Responsive , clean, and so much fun! Room matched the description, check in was super easy, and Robert was able to extend our stay when requested. Will be back for sure !
Guest favourite
Apartment in Kissimmee
4.95 out of 5 average rating, 37 reviews

Peaceful lake view escape

CollinRating, 5 stars3 weeks 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.
Guest favourite
Apartment in Kissimmee
4.94 out of 5 average rating, 17 reviews

Carri-Vision Suite, (Theme-Parks)Orlando/Kissimmee

GavinRating, 5 stars1 month ago
The first thing we absolutely loved about the house was the smell. It was very clean and instructions to everything was very clear. I would definitely recommend this house!!!
Superhost
Apartment in Orlando
4.86 out of 5 average rating, 43 reviews

King Bed/13-16 min Disney & Epic/Pool/Hot Tub

JaylinRating, 5 stars1 week ago
Chalbaud’s place was an amazing stay! Very clean, smaller than the pictures but felt very cozy. Pool was right there and washer/dryer upstairs was convenient for our week long stay. Everything we planned or needed to go to (other than the airport) was no more than a 15 minute drive which was amazing. Only downside for our stay was the water pressure in the shower, it was too light.
Guest favourite
Apartment in Orlando
4.97 out of 5 average rating, 93 reviews

Modern Lake view Condo 1 mile from Disney

AniaRating, 5 stars4 days 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

Quick stats about apartment rentals in Winter Park

  • Total rentals

    10 properties

  • Nightly prices starting at

    ₹3,425 before taxes and fees

  • Total number of reviews

    320 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Winter Park
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