Apartment holiday rentals in Winter Park

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Popular amenities for Winter Park apartment rentals

Weekly apartment rentals

Top guest favourite
Apartment in Orlando
5 out of 5 average rating, 53 reviews

Classy Disney Themed Condo with FREE shuttle!

StephenRating, 5 stars1 week ago
Ideally situated for all the parks to be driven to, shuttle bus worked, bit of patience needed because it picks up at other locations, but hey it free to use 👍. lovely manicured gardens with a good swimming pool and hot tub. Great place to stay for our Disney adventure in a Disney decorated apartment.
Guest favourite
Apartment in Orlando
4.86 out of 5 average rating, 73 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

kaitlyn Rating, 5 stars3 days ago
very good communication and was a great stay
Top guest favourite
Apartment in Orlando
4.95 out of 5 average rating, 87 reviews

Penthouse Lakeview Minutes to Disney/ Universal

TonyRating, 5 stars1 week ago
Jeff was one of the most responsive, friendly, and fair hosts I have ever dealt with. Super flexible and easy going! The place is outstanding, beautiful views, lots of amenities, and close to a lot of places. I will 100 percent be booking at Jeff’s place again when we go back
Guest favourite
Apartment in Florida Center
5 out of 5 average rating, 50 reviews

Boho Retreat: 7 min to Universal & Epic!

LexiRating, 5 stars6 days 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.
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 stars2 weeks 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 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
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.

Pet-friendly apartment rentals

Guest favourite
Apartment 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
Apartment 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
Apartment in Davenport
4.79 out of 5 average rating, 233 reviews

Brand New AwardWinning Renovated Condo Near Disney

JasonRating, 5 stars3 weeks ago
Loved the condo and the resort. Will definitely rent again when we return to Orlando.
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 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 Orlando
4.87 out of 5 average rating, 154 reviews

Amazing Lake Studio-Near INT'L Drive and Parks!

EstherRating, 5 stars2 weeks ago
Dan was so helpful and very great to work with! I was here for a research conference and his place was close to the convention center. He was also flexible, my last day of the conference I asked for a later check out time and he was able to accommodate which I greatly appreciated. His placed was also a short uber to other locations but was also a quiet oasis to come back to and rest. Very grateful to have stayed here!
Superhost
Apartment in Four Corners
4.71 out of 5 average rating, 119 reviews

No BNB fees -Oasis Condo 5 min to Disney

SoniaRating, 5 stars1 week ago
Very beautiful location, calm surroundings and very close to all attractions
Superhost
Apartment 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.

Apartment rentals with a pool

Superhost
Apartment in Orlando
5 out of 5 average rating, 4 reviews

King Studio w/ Balcony | Near Theme Parks

MonicaRating, 5 stars1 week ago
Great deal and a great location! So many amenities to enjoy, we will definitely be back to take advantage of them. It was so nice being close to all of the parks too, but the resort was still very quiet
Top guest favourite
Apartment in Kissimmee
4.98 out of 5 average rating, 179 reviews

303_To Infinity & the Ocean Breeze Apartment

TonyRating, 5 stars2 weeks ago
There's a reason why Rafaela's place has a diamond next to it as a gem. It's in a great location close to all Disney parks, the rooms are decorated just like the photos with Moana and Buzz Lightyear (Toy Story), and there are a lot of thoughtful touches like the wireless charging pads in the bedrooms. The water park was a lot of fun and very walkable too. Whether you want to stay and play at the water park, go to the gym, or use it as a home base for a Disney adventure, there's a lot to like about the space. The beds were comfy too!
Guest favourite
Apartment 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.
Guest favourite
Apartment in Kissimmee
4.96 out of 5 average rating, 55 reviews

4731_205 Minutes from Disney, Incredible Condo 2BR

ManuelRating, 5 stars1 week ago
Great experience at Rafaela’s place. Very easy checkin, both at the entrance gate and in the apartment. The apartment itself is very comfortable, clean, with all the amenities we needed. Rafaela was very responsive and helpful throughout our stay. I would highly recommend her listing and would definitely come back.
Top guest favourite
Apartment in Orlando
5 out of 5 average rating, 68 reviews

Retro Theme! 10 min from Disney! Lake View! MCM

MikeyRating, 5 stars1 day ago
This place was so beautiful and so peaceful. When we went, the pool it was never crowded and the tiki hut was a great addition. We very much enjoyed our stay. We travel to Orlando for volleyball tournaments and this was a great place to stay. The kids said they loved it and it felt like home. Everything was very clean and decorated so nicely and the linens were so nice. We will be returning for sure and I’m sure you will love it too. Thanks for a great place to stay.
Guest favourite
Apartment in Orlando
4.98 out of 5 average rating, 54 reviews

3Bd/ 2 Ba Modern Condo - Vista Cay (4024-203 BD)

YaraRating, 5 stars2 weeks ago
Incredible location, close to everything. Very roomy and beautiful modern look - everything was spotless!
Top guest favourite
Apartment in Orlando
5 out of 5 average rating, 59 reviews

Amazing lake view condo near Disney & Universal.

RichRating, 5 stars1 month ago
This is my family's second time staying at Suzanne's rental. It is a perfect vacation rental if you are staying in Orlando for the theme park/shopping/tourist experience, and want the flexibility of a private home/condo. Everyone is able to stay together with space to unwind after a long day, as well as ability to prepare meals and avoid eating out for breakfast, lunch and dinner. There are plenty of conveniences and restaurants within a 5 min drive or a short walk. Disney/Universal/I-Drive are a quick 20 min drive, Outlets and Disney Springs even closer.
Guest favourite
Apartment in Windermere
4.93 out of 5 average rating, 45 reviews

LuXury Apt with Lake View, Cable & fast WiFi

LoisRating, 5 stars2 weeks ago
The apartment was very nice with a screened in balcony. It had all of the conveniences expected for a comfortable stay. The location was great because it was near plenty of restaurants and shopping, and close to the freeway and the Parks which makes it great for vacationers. The host was very responsive to questions and was pleasant to work with. One thing to note is that the unit is on the second floor and there are no elevators. Otherwise, it was a great choice!

Quick stats about apartment rentals in Winter Park

  • Total rentals

    10 properties

  • Nightly prices starting at

    $51 SGD 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

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