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Vacation rentals in Winter Park

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Winter Park vacation rentals

Stay near Winter Park's top sights

Orlando Science Center289 locals recommend
Orlando Museum of Art215 locals recommend
Harry P. Leu Gardens197 locals recommend
Scenic Boat Tour160 locals recommend
Prato124 locals recommend
East End Market111 locals recommend

Pet-friendly vacation rentals in Winter Park

Top guest favorite
Home in Kissimmee
4.92 out of 5 average rating, 134 reviews

Disney Playhouse, Private Pool & Spa, Near Disney

Paige Rating, 5 stars1 week ago
My family stayed at Yvonne and John's place during our Easter Break vacation and had a blast. The home is very spacious and comfortable. We loved the layout of the home and my family even said they liked it better than our own house! I think the hot tub, pool, and game room probably won them over the most. I loved the extra spaces for our luggage, plenty of clean towels, master bathroom, giant washer and dryer and the extras provided in the kitchen. Walmart is so close, so I was able to get some snacks easily which was convenient. We picked the place because it was so close to the parks and driving was easy in the area. The home was perfect and so comfortable for our vacation. Communication was very easy and clear. Thank you Yvonne and John so much! We hope to get back and recommend your place as a great home in Orlando area. Way better than a hotel!
Guest favorite
Apartment in Kissimmee
4.91 out of 5 average rating, 113 reviews

Modern 3 Bedroom Apartment Near the Theme Parks

RémiRating, 5 stars2 days ago
Très belle maison proposée ! Très confortable, bien équipée, nous avons passé un très agréable séjour. et surtout à proximité des parcs d'Orlando. Nous sommes vraiment très contents !
Guest favorite
Home in Orlando
4.85 out of 5 average rating, 206 reviews

Waterside Pet Friendly Lakefront

SkylaRating, 5 stars1 week ago
This will be my second time staying at Virginia’s Orlando location. My husband and I truly love it so much and will continue to stay here. Virginia is very responsive and is always checking up on you. Her description of the place is accurate. The location is lovely and is extremely safe! I have only good things to say and would recommend this Airbnb to anyone. :)
Top guest favorite
Cottage in Mount Dora
4.93 out of 5 average rating, 104 reviews

Cozy Cottage 3 blocks from town

MaryRating, 5 stars1 month ago
The Cozy Cottage was more than we expected. Very clean, comfortable, felt like home and near downtown. Debbie was very kind, helpful and friendly. Definitely I recommend it.
Superhost
Condo in Kissimmee
5 out of 5 average rating, 3 reviews

Pet Friendly Reunion Condo Minutes from Disney!

HeatherRating, 5 stars3 months ago
Amazing little spot if you are in the Orlando area. Pristine air b&b. I walked into a freshly clean condo with soft music playing on the tv, lights turned on and a plate of snack waiting for me. Communication was wonderful and the door was peaceful and homey. Absolutely would stay here again.
Guest favorite
Bungalow in Mount Dora
4.86 out of 5 average rating, 104 reviews

Renovated "Cozy Bungalow" in Downtown Mt. Dora!!!

JoeRating, 5 stars1 month ago
House was as advertised and clean. Steve was reaponsive and accommodating.
Guest favorite
Home in Kissimmee
4.87 out of 5 average rating, 167 reviews

Close to Disney!

CameronRating, 5 stars1 week ago
Sarah was a very engaging and responsive host. My family enjoyed the place, the kids loved playing pool and swimming in the pool. Would definitely recommend
Top guest favorite
Guesthouse in Sanford
4.95 out of 5 average rating, 270 reviews

Palmetto Pool Retreat

LindaRating, 5 stars1 week ago
Jill is very responsive. The AirBnb was just as described and even had coffee, creamer, and sugar so you don’t have to shop before arriving. Cute little place; very clean and had all that you’d need.

Other great vacation rentals in Winter Park

Superhost
Home in Kissimmee
5 out of 5 average rating, 3 reviews

Dream vacation, near Disney

ChrisRating, 5 stars1 month ago
What an incredible stay we had at Rosario's place! We even extended 2 extra nights. Rosario was responsive, helpful, and so kind - she even left a birthday balloon and some treats for my mom's birthday! The house was impeccable and they were great about everything, from changing dates to heating the pool, and keeping it clean, and the pool was a perfect balmy respite. The next time we're in town (and we will be, this is our old neighborhood!), we will definitely try to book here again. Can't wait to come back!
Superhost
Home in Davenport
4.76 out of 5 average rating, 68 reviews

Casa vacacional

JaniquaRating, 5 stars1 month ago
Me and my Family enjoyed our days there! Miguel was very friendly and nice and welcome us to a little welcome gift I mean who dosen’t love chocolate
Guest favorite
Home in Davenport
5 out of 5 average rating, 5 reviews

New! Windsor Island Resort with pool by Disney 03

IrynaRating, 5 stars16 months ago
Nice house with good layout of rooms. It is very convenient to come with children as there is a lot of entertainment on the territory of the complex. I also liked the themed design of the rooms. Overall, this is a good house for a large and friendly company.
Guest favorite
Condo in Kissimmee
4.9 out of 5 average rating, 120 reviews

D-Gated Resort-5 miles to Disney-2 FREE Water Park

LauraRating, 5 stars3 weeks ago
My husband and I stayed In james apartment with our two children. This was a return trip for us having stayed previously in 2019. We enjoyed our stay just as much this time around. My son and husband are big Star Wars fans so loved the theming of the apartment. Everything was really well maintained and amenities were great. We enjoyed using the clubhouse as well. The location is perfect for visiting all the Disney parks and universal, everything was around a twenty minute drive. James was responsive and helpful to all queries, we hope to return one day soon!
Guest favorite
Cabin in Orlando
4.9 out of 5 average rating, 121 reviews

The Moose Cabin, Luxury Stay

YaritzaRating, 5 stars2 weeks ago
We came here for one night right after a Disney park and felt right at home! Such a nice tiny home! It was a quick and easy check in for us!
Superhost
Home in Four Corners
4.88 out of 5 average rating, 16 reviews

DisneyVacationHomeLazyRiver9021

SharonRating, 5 stars3 weeks ago
This beautiful home worked well for our family…4 couples and 3 small children. Pool and hot tub were great and clean! The house was large and we had a ton of fun! The host was super responsive every time we sent a message. We would definitely come back to this house and would highly recommend it!
Top guest favorite
Cabin in Haines City
4.98 out of 5 average rating, 168 reviews

Nearby Legoland,Disney,Universal,Seaworld and more

RobertRating, 5 stars5 days ago
Great place to stay! Alfredo was very responsive during the whole process from booking to checkout. Exactly as advertised..very quiet, nice and clean! Will be returning for sure! Thanks Alfredo!
Guest favorite
Home in Kissimmee
4.82 out of 5 average rating, 33 reviews

2611-VP Beautiful 4 Bd Home, Lake View & Pool

LindseyRating, 5 stars10 months ago
We loved our stay! We give this house 5 stars and would recommend this place to others. The home was clean, had comfortable beds, fully stocked kitchen, and plenty of room for everyone! We felt right at home! The pool was clean and a good size. The location is great-close to plenty of places to shop, eat, and check out. The neighborhood was quiet and safe. My teenage boys also enjoyed the workout facilities at the club house. This home was perfect for our family! Thank you!!!

Quick stats about vacation rentals in Winter Park

  • Total rentals

    380 properties

  • Total number of reviews

    19K reviews

  • Family-friendly rentals

    180 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    110 properties have a pool

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

Frequently Asked Questions

  • Where should I stay in Winter Park?

    Make yourself at home in Winter Park by choosing from our most frequently booked neighborhoods. We have over 1,050 vacation rentals in Lake Formosa, over 1,990 vacation rentals in Baldwin Park, and over 1,510 vacation rentals in North Orange.

  • Are there vacation rentals with a dedicated workspace in Winter Park?

    Yes! Work meets play with ease at over 210 vacation rentals in Winter Park featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winter Park?

    Four-legged friends are welcome in Winter Park. Choose from more than 120 vacation rentals for guests traveling with pets.

  • Are there Winter Park vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 110 vacation homes with pools in Winter Park, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in bungalow rentals in Winter Park?

    Experience the best of Winter Park with our bungalow rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Winter Park have a gym?

    Absolutely! We offer over 10 apartment rentals with a gym in Winter Park. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Park have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Winter Park. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Park have self check-in?

    Absolutely! We offer over 50 house rentals with self check-in in Winter Park. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Winter Park have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Winter Park. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Winter Park?

    Winter Park has more than 180 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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