Pet-friendly holiday rentals in Winter Park

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Winter Park pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Orlando
4.98 out of 5 average rating, 127 reviews

Modern 3/2 in Ivanhoe Village

MarcelaRating, 5 stars6 days ago
Our stay was fantastic! The townhouse was very clean and well-stocked with everything we needed. He provided great local tips and also very clear instructions. We can’t wait to come back!
Top guest favourite
Home in Orlando
4.97 out of 5 average rating, 127 reviews

Beautiful House Completely Remodeled

LeaRating, 5 stars2 weeks ago
We’ve stayed at Jonny’s place several times and always make it a point to come back when we’re in Florida. Jonny is an amazing host and this home is beautiful and always exceeds expectations. This home is the best AirBnb I have stayed in and matches the description and photos. As always, thank you Jonny, we will be back next year!
Superhost
Home in Altamonte Springs
4.85 out of 5 average rating, 226 reviews

Guest House near attractions

WillRating, 5 stars4 days ago
Would definitely stay here again
Superhost
Home in Longwood
4.85 out of 5 average rating, 124 reviews

The Frog Castle

EshoRating, 5 stars1 month ago
The place was beautiful, clean, and felt upscale. My girlfriend and I had a great time staying here. The space was big, cozy, and well put together. It had everything we needed and made the trip really enjoyable. The lighting, the furniture, and even the layout made it feel like a home away from home. I did see a few roaches during the stay. One was large and I had to kill it, and a few smaller ones were either already dead or barely moving. That tells me pest control is likely in place, not a major thing since I have family in Australia, but I figured it was worth mentioning just to be fully honest. Other than that, everything else was solid. The location was quiet, the vibe was peaceful, and it felt like a perfect spot to relax. Parking was easy, check-in was smooth, and communication with the host was clear and helpful. If the pest issue continues to be monitored, I’d absolutely stay here again and recommend it to others. We truly enjoyed our time and made great memories together.
Superhost
Home in Orlando
4.84 out of 5 average rating, 305 reviews

King Bed | Grill | Pets | Central Location!

SianoahRating, 5 stars2 weeks ago
This Airbnb is definitely one we will keep in rotation. With an elderly in-law, we needed a place with a fourth bedroom. The bonus was the pool and we took full advantage of that just to relax and enjoy. Everything we needed was close by and easy to get to. All in all the hosts home felt like home. We hope to stay again in the future.
Top guest favourite
Home in Minneola
4.98 out of 5 average rating, 128 reviews

Pool + Heated spa Family friendly King suite Oasis

JohnRating, 5 stars2 weeks ago
House, yard and pool were exactly what what we were looking for! Thank you to our hosts!
Guest favourite
Home in Altamonte Springs
4.87 out of 5 average rating, 166 reviews

Elegant, Spacious Three Bedroom Residential House.

JacquelineRating, 5 stars2 weeks ago
The house was spotless and we felt right at home. It certainly helped that the location was 12 minutes away from the wedding that we were attending. Everything was clean and in place and we were able to easily find everything we needed in the kitchen as well as the bathrooms. I would definitely recommend this house if you have to stay in the area.
Guest favourite
Home in Thornton Park
4.93 out of 5 average rating, 109 reviews

Updated Home* 2 King Bed Suites * Downtown Orlando

VincentRating, 5 stars4 days ago
Great location minutes from downtown Orlando, but on a very peaceful street minutes walk from a beautiful lake. House was clean with good parking. Our Host Andy was very responsive whenever we had questions or needed any support. Would definitely recommend.

Pet-friendly home rentals with a pool

Guest favourite
Flat in Orlando
4.92 out of 5 average rating, 151 reviews

Apartment, 7 Min to Orlando Airport/ Lake Nona

CamilaRating, 5 stars2 weeks ago
Eileen was so kind and very responsive with any inquiry we had. The house was beautiful and very accommodating. If I ever need to come to the area, I’ll definitely be using this Airbnb.
Guest favourite
Cottage in Orlando
4.94 out of 5 average rating, 174 reviews

Mills Cottage

NicoleRating, 5 stars1 week ago
This place was spectacular. Sometimes with an air b and b experience, you hope the place is as pleasant as the pictures. This was such a wonderful surprise. Immediately it felt cozy and peaceful, surrounded by nature, wood and botanical details everywhere. But it surpassed that - Every detail of this place had been touched with diligent character, you immediately recognized the owners of this place genuinely cared down to the last morsel of decorations, plates, games and books. Nothing was forgotten. I HIGHLY recommend paying for the extra amenities which made our stay incredible; we booked an extra day just to relax and absorb the relaxation. It was one of the best parts of my trip to Orlando. I cannot speak highly enough about this place, I feel like we’ve found a rare gem in the business of air b and b’s. I cannot wait to book our next stay. This place made you fall in love with Orlando and treating yourself to a hidden oasis away from the modern rat race. INCREDIBLE!
Top guest favourite
Guest house in Orlando
4.92 out of 5 average rating, 110 reviews

Kyle's Place - Private Unit, Pool + Laundry Room

JamaiRating, 5 starstoday
Had more than what we needed and was a great spot to recharge from the daily adventures we had. Would book again if in the area.
Guest favourite
Home in Oviedo
4.9 out of 5 average rating, 309 reviews

🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s

DesireeRating, 5 stars2 days ago
First time in Orlando. It was a pleasant and comfortable stay.
Top guest favourite
Home in Minneola
4.98 out of 5 average rating, 162 reviews

Spacious Getaway ~ Heated LED Pool & Ping Pong

LaTishaRating, 5 stars3 days ago
We had a great stay. The residence was beautiful and came with everything we needed. Our 4 and 1 year old enjoyed the toys provided. The pool was private and relaxing. Neighborhood very quiet with kind neighbors. Thank you for everything ❤️
Guest favourite
Home in Orlando
4.88 out of 5 average rating, 202 reviews

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

JoyceRating, 5 stars2 weeks ago
We where in Orlando to go to my granddaughters graduation & this home just made it a perfect vacation - so comfortable - & clean & the pool & outside area was amazing !!
Top guest favourite
Apartment in Orlando
4.98 out of 5 average rating, 178 reviews

Lakefront Resort Condo near Disney & Universal

KristinaRating, 5 stars1 week ago
We had an amazing stay! The place was perfect in every way; perfect location and easy to get to…as we used Uber a lot. Close to all the Disney parks and Disney Springs….less than 15 min Uber. There is a Starbucks next to the building which was awesome. Nicoleta is a fantastic host, replies right away and gave us wonderful restaurant suggestions. Communication was great and she is very attentive. Again, very impressed with the place. All the amenities you need and very comfortable and clean. Was also a huge bonus to have 2 bathrooms.
Top guest favourite
Guest suite in Orlando
4.97 out of 5 average rating, 481 reviews

Vacation & Oasis Mood with #1 location - Pool

StefanRating, 5 stars1 day ago
Nice home in a private and quiet neighborhood. Interior and decorations are selected with love and good style. Nice outside area with pool, BBQ and several outdoor seating options. The owner is super friendly and proactive. We really enjoyed our stay and can warmly recommend the home.

Private, pet-friendly home rentals

Superhost
Apartment in Winter Park
4.83 out of 5 average rating, 99 reviews

Lovely Winter Park Home close to Hospitals !

LisaRating, 5 stars1 week ago
This place was beyond our expectations, very convenient to where we needed to go and quiet as well as well supplied.
Superhost
Home in Winter Park
5 out of 5 average rating, 7 reviews

Casa Winter Park

CristinaRating, 5 stars3 days ago
This was a spacious and hospitable place. Juan was responsive and understanding. The house was sparkling clean and very beautiful and comfortable. I didn't do any cooking but this was an extremely well-appointed kitchen. Pool is lovely. We loved our stay here!
Top guest favourite
Guest house in College Park
4.98 out of 5 average rating, 81 reviews

Amazing New Pool House!

KateRating, 5 stars2 weeks ago
David’s place was perfect. Comfortable clean and very convenient. He was very accommodating and answered any questions I had in a timely manner!!! I plan on booking again when I come back to Orlando!! Thanks David for a being a great host!
Guest favourite
Home in Winter Park
4.95 out of 5 average rating, 20 reviews

New built Private Studio Orlando/Winter Park area

GregoryRating, 5 stars2 weeks ago
This sweet little suite met all my needs for a week visiting friends. There was an internet problem one day, but Diana stayed in communication with me and the malfunction was corrected in a timely manner. The place is clean and well-appointed. I highly recommend it, and I would definitely return.
Top guest favourite
Guest house in College Park
4.97 out of 5 average rating, 438 reviews

The Coach House- 2 bedroom/3 bath Orlando Getaway!

AndreaRating, 5 stars2 weeks ago
we had a wonderful stay at the Coach House, it was well set up, clean, and in a lovely neighborhood. the hosts were communicative, helpful, and very friendly. we would highly recommend anyone staying in the Orlando area stay at this accommodation.
Guest favourite
Home in Audubon Park
5 out of 5 average rating, 7 reviews

The House at Starlab!

DiamondRating, 5 stars1 month ago
We had a fantastic stay! The place was absolutely amazing—clean, stylish, and incredibly cozy and private. We especially appreciated the opportunity for early check-in's (our flights ended up being delayed so we didn't need it after all, but had asked ahead of time, and we would have been able to!). The location was perfect—just a short walk to East End Market and other local gems. The snacks and wine left for us were such a thoughtful touch and made us feel instantly welcome. The host was warm, friendly, and very responsive throughout our stay. We couldn’t have asked for a better experience and would definitely love to stay here again!
Top guest favourite
Home in College Park
5 out of 5 average rating, 10 reviews

3BR Oasis DT ORL, Full Kitchen & Fenced Yard!

KaylaRating, 5 stars1 week ago
What a nice place to stay while visiting friends and Epic Universal. Close to everything 15 min drive or so. Nice bedding and the blankets were a fan favorite. So nicely decorated! The fenced in back yard was great. Beautiful front entrance. Felt like home.
Guest favourite
Home in Orlando
4.94 out of 5 average rating, 83 reviews

Colonialtown Bungalow

StephanieRating, 5 stars4 weeks ago
This is a great location! Everything you could need and more is around the beautiful area. The house is sooo clean! You never know about an older home regarding the smell and this house smells GREAT! Great stay for a small group. The backyard is wonderful and I got to enjoy catching some rays while there.

Quick stats about holiday rentals that are pet-friendly in Winter Park

  • Total rentals

    120 properties

  • Nightly prices starting at

    ₹2,569 before taxes and fees

  • Total number of reviews

    6.5K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Rentals with a pool

    40 properties have a pool

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

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