
Pet-friendly holiday rentals in Winter Garden
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Winter Garden
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Winter Garden pet-friendly home rentals
Pet-friendly house rentals

Beautiful house in Orlando/heated pool/Disney
We absolutely loved staying at Ernesto’s! It was very spacious, beautiful, clean, and not far from everything. The pool is a very nice touch after a long day! Walmart is conveniently no more than 5 mins away and Disney isn’t far at all. We would absolutely stay when coming again!

Beautiful House Completely Remodeled
We loved our stay. The house was clean and comfortable, and located in a super convenient location. We'll definitely come back the next time we come to Orlando!

Orlando Cactus House! 15min from Epic Universe
Good stay! Close to everything in the area and so cute!!

Private Pool & Spa, Close Disney, Disney Playhouse
Very clean and convenient transportation

Private pool home near Downtown
Great house. Great host. Always attentive and responsive. 2nd stay. Will go for a 3rd

The Orlando Retreat.
Had a wonderful time!! Pool was great and house was very comfortable! We always feel right at home this is our second stay!! 😁

3,000 Sqft Historic Home With Pool Near Everything
This was the perfect place to stay. This home is beautifully decorated, and such a nice little quiet retreat. I felt like I was staying in a home that was showcased in a magazine. The beds are so comfy and the pool is serene. I had the most relaxing weekend ever, thank you Nicole!

Spacious Home with Pool & Hot Tub near Downtown
We had a wonderful stay and would definitely book again. Tina was a wonderful host. Thank you so much for a memorable place to stay and the wonderful recommendations. We had a great time.
Pet-friendly home rentals with a pool

Comfy 4BR near Disney/pool and Hottub
Felt at home when we arrived. Large rooms, plenty of space for our family. Pool was nice. Conveniently located. Simple, easy checkout. Our family would stay here again.

Villa, Games, Theater, Nr Disney, Great Pool Heat
Our kids and family loved the house ! Pool was nice size that over looked the lake was the best part. It close to Disney about 15-20 mins . House was huge 6 bedrooms and every bedroom had a bathroom . We will hopefully come back again

Entire clean comfortable house
A perfect AirBnB for a family. Place was immaculate with nice, comfortable furniture. Owners are super responsive (and we had a lot of requests). We’ve already recommended this place to many family and friends. It’s a terrific value.

Cozy Townhouse in Kissimmee, near Orlando!
Maria's place was super cozy. It had everything we needed and then some. the property is beautiful. Pools were nice. and the staff at the gates were very welcoming. No problems. very relaxing.

Modern Coastal Farm House/Pool+Jacuzzi/near Disney
My family really enjoyed our vacation. Stay at this location. It was very, very clean well appointed and exactly as advertised. What was the best part of all was the host who took care of? Everything answered all questions and made sure that we were very much right at home that was fantastic. If you need room to spread out for your family or room to relax, there are plenty of places in this house. The pool and hot tub worked perfectly and everything simply was great. We really enjoyed this. Thank you very much. We will see you again.

No BNB fees -Oasis Condo 5 min to Disney
Very beautiful location, calm surroundings and very close to all attractions

Downtown Orlando Garden Retreat
Ernie and Jeff were immaculate hosts and now considered friends! The property was beautiful and well curated, but it was an environment to nurture and enrich the soul!! This will be an annual, if not bi-annual trip! Close to everything, great food and dining experiences all within 2-5 miles!! Ernie is a wealth of knowledge and is passionate to ensure his guests/new friends are cared for with the utmost of diligence. Thank you for an amazing vacation and we now consider them extended family! Job well done new friends! We miss you already! Much love!

Lakefront Resort Condo near Disney & Universal
We loved our stay at Nicoleta's! Everything was very clean and exactly as described. The view was beautiful and truly the cherry on top of a perfect stay! We will definitely stay again next time we are in the area!
Private, pet-friendly home rentals

The silver cottage
This was my second time staying here, and once again, it was fantastic! The place is super clean, the location is excellent, and Vanessa is always quick to respond and very helpful. Highly recommend — I’ll definitely be back!

Lake Front Luxury in Private Cottage
We loved our stay on the lake. Thank you:)

Tiny House | Airport & Downtown Orlando 15 Min
I had a very good experience, the place was very beautiful, clean, and cozy. The host was very attentive.

Family Vacay with Pool near WDW!
I just want to thank Enma and all of the hosts who helped make my little family’s first vacation feel so perfect! This is also my first house Airbnb experience (I’ve been in hotel style Airbnb’s) before but I used to be more of a resort type of girl. Now my teen daughter says we should do a house instead of resorts every year!! I miss this home already and so much that now my husband and I are discussing owning one of these ! The home much nice and cozy and so cleannn! The beds felt amazing ! I miss the pool already !! Thank you . Thank you !!!!

Lakefront in West Orlando Florida
My family and I had a wonderful stay at Michele's place! Everyone loved it. The home exceeded all of our expectations. Check in was a breeze, the home was in excellent condition and beautiful, it was well equipped with everything we needed, and the back porch on the lake was wonderful. Michele is a terrific host and made everything very easy. No hassles, easy to follow instructions, check-out was simple and not overbearing. We highly recommend her home and will definitely return!

Amazing New Pool House!
We had an excellent stay in David and Nadia's pool house. Nadia was very responsive, friendly, and proactive host and made sure our visit went smoothly. The place matched the photos and description perfectly -- it's a real gem! The pool house itself is modern, attractive, and comfortable with everything you need for a comfortable stay. The shared backyard is such a lovely place to spend time. We especially enjoyed the pool and putting green. Overall we had a great trip and would happily stay there again.

Magnificent Lakefront Home•Swim&Relax•Long Stay OK
Absolutely wonderful place that was breathtaking! The view was amazing from everywhere and the home was straight out of a movie!

3BR Oasis DT ORL, Full Kitchen & Fenced Yard!
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.❤️
Quick stats about holiday rentals that are pet-friendly in Winter Garden
Total rentals
30 properties
Nightly prices starting at
₹3,462 before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- ESPN Wide World of Sports
- Amway Center
- Epcot
- Magic Kingdom Park
- Reunion West
- Aquatica
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Walt Disney World Resort Golf
- Island H2O Water Park
- Blue Spring State Park
- ICON Park
- Universal CityWalk
- Universal's Islands of Adventure