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 Longwood
4.92 out of 5 average rating, 203 reviews

Cozy 3 Bedroom Home, Great location!!

JosephRating, 5 stars2 weeks ago
Ahmad and his team were great hosts and the property was very enjoyable. Ahmed was very helpful, but a quicker response time on communications would have even better!
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.
Superhost
Home in Altamonte Springs
4.85 out of 5 average rating, 227 reviews

Guest House near attractions

RichardRating, 5 stars1 week ago
Very clean. Nice house, would use again.
Guest favourite
Home in Altamonte Springs
4.87 out of 5 average rating, 166 reviews

Elegant, Spacious Three Bedroom Residential House.

JacquelineRating, 5 stars3 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 Orlando
4.93 out of 5 average rating, 109 reviews

Updated Home* 2 King Bed Suites * Downtown Orlando

VincentRating, 5 stars1 week 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.
Guest favourite
Home in Orlando
4.84 out of 5 average rating, 212 reviews

Waterside Pet Friendly Lakefront

KennethRating, 5 stars2 weeks ago
Place was exactly as described. Virginia was a great host. Would stay here again.
Guest favourite
Home in Clear Lake
4.92 out of 5 average rating, 456 reviews

Pet OK/Big Backyard/Fast WiFi/Washer & Dryer.

CalebRating, 5 stars1 day ago
This house is so cozy and lovely! We attended a concert at Camping World Stadium and Miguel’s home was the perfect fit, it felt private but was nearby, and there are 2 bikes provided that we took to the venue (which saved us from sitting in traffic for 30 minutes after the show!). You could easily walk to the venue as well if you wanted. Highly recommend staying here!

Pet-friendly home rentals with a pool

Superhost
Condo in Winter Park
4.83 out of 5 average rating, 98 reviews

Lovely Winter Park Home close to Hospitals !

MichaelRating, 5 stars1 month ago
This was my 4th time staying there to visit family who live in the area. I’d say picking the same place 4 times is the ultimate complement of the condo unit.
Superhost
Home in Winter Park
5 out of 5 average rating, 7 reviews

Casa Winter Park

CristinaRating, 5 stars1 week 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!
Guest favourite
Cottage in Orlando
4.94 out of 5 average rating, 174 reviews

Mills Cottage

NicoleRating, 5 stars2 weeks 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
Guesthouse in Orlando
4.92 out of 5 average rating, 110 reviews

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

JamaiRating, 5 stars4 days ago
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, 310 reviews

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

DesireeRating, 5 stars6 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 stars1 week 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
Apartment in Winter Park
4.95 out of 5 average rating, 79 reviews

B - Modern Elegance! 3 blocks to Park Ave

AliRating, 5 stars4 months ago
Very nice unit, very clean, good size bedrooms, and ample initial supplies. All appliances were in good condition. Nice condo complex, quiet and convenient location close to restaurants and shops. We used the outside barbecue a few times which was great.
Guest favourite
Home in Orlando
4.88 out of 5 average rating, 202 reviews

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

JoyceRating, 5 stars3 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 !!

Private, pet-friendly home rentals

Top Guest favourite
Guesthouse in Thornton Park
4.93 out of 5 average rating, 309 reviews

Charming Thornton Park Guesthouse

JanineRating, 5 stars3 weeks ago
I loved the thoughtfulness of the space and the location. They are very responsive hosts and care about your comfort!
Guest favourite
Home in Winter Park
4.88 out of 5 average rating, 25 reviews

Winter Park - Cozy retreat near Lake Killarney

JulieRating, 5 stars5 months ago
The house was charming and close to all the things Winter Park has to offer.
Top Guest favourite
Guesthouse in College Park
4.98 out of 5 average rating, 82 reviews

Amazing New Pool House!

KatieRating, 5 stars4 days ago
Super cute and quaint, easy to access. Daniel and his family were great hosts, easy to go back and forth with. Was proactive with sharing the backyard space and helpful with anything we needed. The space was so nice and clean, just enough space. Great area also, so much around for shopping and eating.
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 stars3 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.
Guest favourite
Home in Audubon Park
5 out of 5 average rating, 7 reviews

The House at Starlab!

DiamondRating, 5 stars2 months 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, 12 reviews

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

DomineRating, 5 stars1 day ago
Such a lovely and cute place! We will definitely be back if we are in Orlando again! The space was perfect for us and a calming retreat to come home to.❤️
Guest favourite
Home in Orlando
4.94 out of 5 average rating, 83 reviews

Colonialtown Bungalow

StephanieRating, 5 stars1 month 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.
Top Guest favourite
Tiny home in Orlando
4.98 out of 5 average rating, 40 reviews

FunTropicalTinyGemUCF

ChrisRating, 5 stars5 days ago
Great host, handled everything from checked in to check out great. very responsive, great place just to relax.

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

  • Total rentals

    120 properties

  • Nightly prices starting at

    $46 AUD 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

Destinations to explore