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Pet-friendly vacation rentals in Winter Garden

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Popular amenities for Winter Garden pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
Home in Orlando
4.93 out of 5 average rating, 27 reviews

Pet-Friendly Bungalow Near Downtown Orlando

LauraRating, 5 stars1 week ago
Perfect for our trip! Loved the pet friendly atmosphere while still being clean! If we had a cat the catio would have been so fun! The plants were so nice too. Easy check out and the beds very comfy! Megan was a great host!
Guest favorite
Home in Orlando
4.97 out of 5 average rating, 107 reviews

Modern 3/2 in Ivanhoe Village

MelissaRating, 5 stars2 weeks ago
Very nice place. In a walkable neighborhood. Nicely updated inside and host was very attentive.
Guest favorite
Home in Orlando
4.97 out of 5 average rating, 117 reviews

Beautiful House Completely Remodeled

JulianaRating, 5 stars1 month ago
Thank you so much Jonny for having us The house is beautiful, clean and perfect Me and my family have so much fun together.. The neighbor is great, the backyard for the dogs with fence and privacy.. we definitely came back soon. Appreciate it 🙌🏻
Guest favorite
Home in Winter Garden
4.78 out of 5 average rating, 68 reviews

Downtown Winter Garden Mid Century Hipster

KrishaRating, 5 starstoday
We had a great stay! The house was clean, had everything we needed. Great location. We will definitely stay here again!
Guest favorite
Home in Clear Lake
4.93 out of 5 average rating, 441 reviews

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

BrendaRating, 5 stars1 week ago
Miguel was an awesome host! He was very attentive and accommodating to our request. He did reach out to see how we were enjoying the space. This space is very nice and cozy. We felt right at home! No thoughts of safety concerns at all. The temperature was a little cooler than we expected and we never touched the air conditioning-It was pretty cool inside and very clean. I really liked the motion night lights though out the house-allowing you to maneuver in an unfamiliar space at night with ease. Big kitchen and multiple utensils and cookware for our breakfast and dinner meals. Huge backyard for my German Sheppard to roam around. Didn’t get the chance to use the two bikes that were parked in the foyer, this was another nice added benefit. Overall, Miguel’s checkin instructions and all the information regarding this space were spot on. Could not have asked for a better spot. You were in fact a Super Host during our stay. Will mark this as a nice option to return again when visiting Orlan
Guest favorite
Home in Orlando
4.96 out of 5 average rating, 48 reviews

3 Bedroom Home, Budget Friendly!+Fully Fenced Yard

MarkiRating, 5 stars3 months ago
Loved our stay! Back yard was perfect for the dogs. Neighborhood was off the main road and very quiet.
Guest favorite
Home in Kissimmee
4.88 out of 5 average rating, 183 reviews

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi

RolandaRating, 5 stars1 month ago
I’ll definitely stay here again!
Guest favorite
Home in Apopka
4.87 out of 5 average rating, 132 reviews

Country Pool home on 2 acres-30 minutes to Disney

WilliamRating, 5 stars3 weeks ago
We had a fantastic stay. Property was as described. Clean with a lot of privacy. Check-in and check-out were both easy. The pool, playground, and outdoor seating enhanced our family stay. Host was friendly and was easy to communicate with. Would stay again.

Pet-friendly home rentals with a pool

Superhost
Home in Davenport
4.83 out of 5 average rating, 6 reviews

Cozy & modern home 4 bed/3 bath/private pool

AmberRating, 5 stars1 month ago
The home was cozy, beautiful, and welcoming. It was exactly as its pictured. It was just what we needed for our 2 week stay. Monique and Ron were very kind, respectful, and responsive to any of our questions and concerns. Overall we had a such an amazing stay. Was super sad to leave but looking forward to future bookings.
Guest favorite
Home in Orlando
5 out of 5 average rating, 114 reviews

Private pool home near Downtown

DiegoRating, 5 stars2 weeks ago
My girlfriend and I enjoyed our stay. It’s a great place to stay if you want somewhere quiet and peaceful. There’s plenty of places to eat nearby. Very clean and it looked like the pictures and smelled good when we walked in.
Guest favorite
Home in Davenport
4.88 out of 5 average rating, 60 reviews

Modern/Luxe Vacation, close 2 Disney, Heated Pool

HarryRating, 5 stars3 days ago
We thoroughly enjoyed our stay at this house. It had everything we needed. The pool was great and heated to our preferred temperature. Our host could not have been any better. He always responded to our questions and concerns within a short period of time. The one downside of the location was the traffic noise. Very noisy. Other than that it was a wonderful trip.
Guest favorite
Guesthouse in College Park
4.97 out of 5 average rating, 68 reviews

Amazing New Pool House!

KathleenRating, 5 stars3 weeks ago
Thank you, Dave, for a very comfortable stay at your lovely Pool House. It was just as described - I felt safe and welcome. I’m hoping to be back soon and would love to return to your quiet and peaceful space. Thanks again!
Guest favorite
Townhouse in Kissimmee
4.94 out of 5 average rating, 53 reviews

9027-WW Beautiful 5 Bedroom Pool Home

JuanRating, 5 stars1 month ago
I recently stayed at this charming townhome for a weekend getaway, and it was absolutely perfect. From the moment we arrived, we were impressed by how clean and welcoming the space was. The townhome is beautifully decorated and has all the amenities you could need for a comfortable stay, including a fully stocked kitchen, spacious living area, and cozy bedrooms with plenty of linens and towels. Communication with the host was excellent. They were quick to respond to any questions we had and made sure we had everything we needed during our stay. Overall, this townhome provided the perfect base for our trip, and we would definitely stay here again in the future. Highly recommended!
Superhost
Home in Kissimmee
4.68 out of 5 average rating, 22 reviews

Vacation Home with Pool & Spa near Disney

StephanieRating, 5 stars4 months ago
It was very peaceful and a nice house! Thank you
Guest favorite
Townhouse in Orlando
4.7 out of 5 average rating, 114 reviews

4 Rooms, Lake, Pool, Hot Tub, Bocce Ball, Putting

Lisa AnnRating, 5 stars1 month ago
Wow Wow Wow! Literally such an amazing, cozy place. I could’ve stayed here forever!! Lake and dock were beautiful and the home was so cozy and perfect! The garage was fun with all the games and it was just a perfect house!! The host was literally so responsive and nice. I can’t even say enough about how great this experience was. We didn’t want to leave!
Guest favorite
Home in Davenport
5 out of 5 average rating, 11 reviews

4/2 home with Pool, BBQ, Playground near Disney

GabrielaRating, 5 stars2 months ago
I recommend this place 💯

Private, pet-friendly home rentals

Guest favorite
Cottage in Lake Mary
4.91 out of 5 average rating, 55 reviews

Cozy quiet cottage

TommyRating, 5 stars2 months ago
Bob is super accommodating and nice. The place is exactly what you see in the picture. The area is super safe, you can leave your doors unlocked, that's how safe it is. God bless you Bob
Guest favorite
Home in Orlando
4.94 out of 5 average rating, 89 reviews

24/7 HomeCare Group

DeannaRating, 5 stars1 week ago
Amazing place to stay! Comfy beds with a very relaxing feel. Just a heads up for anyone staying, the master bath shower/tub is a sit-in accessibility tub and temperature runs very hot with minimal controls (I had to Google the brand to find the controls). Home was very clean and smelled amazing! Back patio made for a very chill environment. Loved every minute of my stay! Would definitely stay again!
Guest favorite
Home in Davenport
5 out of 5 average rating, 17 reviews

Disney Proximity: Luxury 5BD Home

MindyRating, 5 stars3 months ago
We had a beautiful stay and enjoyed the private pool with our infant. We felt right at home!
Guest favorite
Home in Orlando
4.85 out of 5 average rating, 55 reviews

Private luxury home w additional Suite on 0.6 acre

DianeRating, 5 stars2 weeks ago
The home was beautiful. Nice quiet area. Definitely a lot of space for a large family! Awesome decor and very clean. The only downfall for us is it was a little further from Disneyland than we wanted to be. However have we of had more time to relax and enjoy the house it would have been perfect. If our next visit is not so rushed then we would definitely consider this beautiful spacious home again.
Superhost
Home in Kissimmee
4.89 out of 5 average rating, 27 reviews

Pelican House

JessicaRating, 5 stars1 month ago
Our family had a great stay at The Pelican House. Donna was very responsive and friendly. The house matched its description. Very clean, comfy beds and close to all the parks. Thank you for the outstanding stay.
Guest favorite
Home in Clermont
5 out of 5 average rating, 8 reviews

Sunset Cove at Champions! Book this very private

CathleenRating, 5 stars2 months ago
Sue was an excellent host. She was responsive to emails and was proactive in making sure we had everything we needed. The neighborhood was very private and quiet. The house was very nice, the yard was well kept, and the heated pool worked very well in the cooler temps. Would stay again!
Guest favorite
Townhouse in Kissimmee
4.93 out of 5 average rating, 30 reviews

Limited Deal! Hot Tub, Pool & Pet-Friendly Stay!

EricRating, 5 stars2 months ago
Great place to stay for visiting Disney. Great communication from the host.
Guest favorite
Home in Oviedo
4.88 out of 5 average rating, 25 reviews

Cozy Knight Haven

JoelRating, 5 stars1 day ago
We enjoyed our stay at Nicole’s place! It was clean and comfortable and had everything we needed! Nicole is very responsive and helpful. We would stay here again, if we are ever in the area again.

Quick stats about vacation rentals that are pet-friendly in Winter Garden

  • Total rentals

    30 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    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

Destinations to explore