Pet-friendly vacation rentals in Winter Garden

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Winter Garden pet-friendly home rentals

Pet-friendly house rentals

Top guest favorite
Home in Orlando
4.94 out of 5 average rating, 31 reviews

Pet-Friendly Bungalow Near Downtown Orlando

StephanieRating, 5 stars3 weeks ago
Megan's place was everything we needed. We felt right at home and my dog was very happy with the house and the backyard. Totally fenced in yard was safe and secure for my fur baby and the neighborhood was super quiet and cute. Megan was very responsive if I had any questions and the instructions to get in were super easy. I am so very pleased with the comfort of the beds and how wonderful the space was. I will definitely be staying here again hopefully soon. If you need a safe, pet friendly place to stay close to just about everything this is the place for you and your pets. Highly recommend!!!!! 5 stars from me and my 4 legged friend.
Guest favorite
Home in Orlando
4.97 out of 5 average rating, 114 reviews

Modern 3/2 in Ivanhoe Village

DanaRating, 5 stars2 weeks ago
Frank was a wonderful host! His place was beautiful. Wonderful location and big enough for 6 of us to have our own space. Quite a few walkable restaurants, coffee shops, tea shops, etc. I do wish there were TVs in the bedrooms, but besides that a fantastic stay!
Top guest favorite
Home in Orlando
4.97 out of 5 average rating, 121 reviews

Beautiful House Completely Remodeled

PhillipRating, 5 stars1 week ago
Jonny was a fantastic host and the house was absolutely perfect. 10/10 would stay again and probably will rebook soon!
Superhost
Home in Kissimmee
4.82 out of 5 average rating, 88 reviews

Great Lake View - Pet Friendly

JulianneRating, 5 stars1 week ago
My family and I had a great stay ! My two small pets were welcome which was great because leaving them at home would’ve made us worry. There are many restaurants nearby which is amazing! There is an aldi’s, Walmart, and Publix nearby as well ! The house is ever big and spacious ! There’s a half bathroom downstairs and 4 bedrooms upstairs as well as 3 bathrooms upstairs. The upstairs is carpet. We had a great family vacation ! There are some cameras outside in the front and back, but we felt very safe and like we had our privacy ! Truly a great host thank you !
Guest favorite
Home in Winter Garden
4.77 out of 5 average rating, 70 reviews

Downtown Winter Garden Mid Century Hipster

StephanieRating, 5 stars4 weeks ago
Exactly what we needed! Very spacious, clean, and welcoming. Great spot for our family of 4 with a toddler. Appreciated the snacks and bottle of wine. As we were visiting family, we will definitely book to stay here again when we are in town again.
Guest favorite
Home in Clear Lake
4.93 out of 5 average rating, 444 reviews

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

DarrylRating, 5 stars2 weeks ago
This house was really nice. Very close to a lot of good restaurants and businesses. Neat.. organized.. convenient. Really good looking place just like the pictures. Kid friendly as well. Definitely would stay again!
Guest favorite
Home in Orlando
4.96 out of 5 average rating, 48 reviews

3 Bedroom Home, Budget Friendly!+Fully Fenced Yard

MarkiRating, 5 stars4 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, 186 reviews

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi

SamRating, 5 stars1 week ago
We had originally booked another property on our vacation, which the host canceled as we were arriving in town…we managed to find this place, which was great and had instant approval/check-in. We found the place easily…it’s in a quiet neighborhood…Walmart is less than a mile away, so stocking up is easy. Tetyana was incredibly responsive...through no fault of her own, the internet was not functioning when we arrived (they had new grass put in the the workers cut the internet lines). She had a technician out the next morning and everything was fixed right away. The pool can be heated, which was chose to do -- very glad we did (it's an extra fee, but was well worth it, as we could swim into the evening and still be comfortable). All in all, it was a great house and Tetyana is an outstanding host. Book with confidence.

Pet-friendly home rentals with a pool

Superhost
Home in Orlando
4.76 out of 5 average rating, 42 reviews

Pool and Sauna in Orlando

JordanRating, 5 stars2 weeks ago
The place was very spacious worked for my fairly large group of 8 people! Pool was a great temp, and sauna easy to work. If you’re planning to cook or use this as a base camp, be prepared to bring all of your kitchen cookware and oils and spices! But great for hosting big groups, gathering, and fun. They offered to clean everything and give us an easy exit! :)
Superhost
Home in Davenport
4.56 out of 5 average rating, 9 reviews

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

MargaritaRating, 5 stars1 week ago
I had a fantastic 5-day stay at this Airbnb! Monique was incredibly attentive and responsive to all my messages. The house was perfect for accommodating my family, and we felt right at home. I will definitely book again. Thanks again, Monique!”
Top guest favorite
Home in Orlando
5 out of 5 average rating, 121 reviews

Private pool home near Downtown

FrankRating, 5 stars1 week ago
Kyle was a very responsive and friendly host. We especially noted the little details and home amenities of the place. Light switches were labeled, which was a great help. The location is in walking distance to some of Orlando’s very best restaurants. Fantastic stay overall!
Guest favorite
Home in Davenport
4.89 out of 5 average rating, 61 reviews

Modern/Luxe Vacation, close 2 Disney, Heated Pool

HarryRating, 5 stars1 month 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.
Top guest favorite
Guesthouse in College Park
4.97 out of 5 average rating, 71 reviews

Amazing New Pool House!

AngieRating, 5 stars3 weeks ago
Amazing little pool house nestled in a quiet environment. David’s place was perfect for relaxing after a long day at Disney parks. The pool and hot tub were an added bonus and scheduling a time with David for the hot tub to be a perfect temp was very convenient. David was very responsive. Bed was very comfortable and the shower / bathroom is pristine. The back yard was beautifully landscaped and had loungers and table area for sitting and relaxing. Great stay and David’s and located right off interstate. We will be back when in Orlando area again.
Top guest favorite
Townhouse in Kissimmee
4.94 out of 5 average rating, 54 reviews

9027-WW Beautiful 5 Bedroom Pool Home

JuanRating, 5 stars2 months 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!
Guest favorite
Townhouse in Orlando
4.71 out of 5 average rating, 116 reviews

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

DaciaRating, 5 stars1 month ago
Stayed for 2 nights and it was perfect! Exactly like the photos. The house was spacious with a lot of amenities! Total of 6 adults and 1 kid for our stay. More than enough beds for everyone and lots do for entertainment in the home. Highly recommend for a large group and/or kids. Location was great; within 10-15mins from restaurants, stores, and downtown.
Guest favorite
Home in Davenport
5 out of 5 average rating, 12 reviews

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

ShirleenRating, 5 stars3 weeks ago
Our stay here was great! The home is big and beautiful, the yard is spacious and great for dogs and kids. We had so much fun playing games in the outdoor room and watching movies at night. The kitchen had a bunch of pots and pans easy to cook meals. We would definitely stay again. Thank you for having us!

Private, pet-friendly home rentals

Top guest favorite
Home in Orlando
4.95 out of 5 average rating, 96 reviews

24/7 HomeCare Group

LisaRating, 5 starstoday
This house is perfect for a family trip. All of the rooms were spacious and the house was very clean. The fenced back yard was perfect for our dog. There were so many extra touches, like snacks in the pantry, a coffee bar, dog toys and a craft area with lots of activities. We would absolutely stay again!
Guest favorite
Villa in Davenport
5 out of 5 average rating, 19 reviews

Disney Proximity: Luxury 5BD Home

GeorgeRating, 5 stars1 week ago
Host was responsive and clear, the house in our opinion looked better than the photos. Pool area was exactly what it appeared to be on the photos, not too big but also not that small. Check in and out was an absolute breeze. We absolutely loved the upstairs area, the neon lights were a great touch. If you book this house and see a hot water feature for the pool and think you don’t need that, it’s Florida. Yeah we did too and immediately asked the host for the feature once we touched the water. And it was the best thing we could’ve done. It was 80°+ degrees outside and the water was amazing.
Guest favorite
Home in Orlando
4.86 out of 5 average rating, 56 reviews

Private luxury home w additional Suite on 0.6 acre

IgnatiosRating, 5 stars1 month ago
My family and I travel all around the world. This is by far one of the best Airbnb we have ever stayed at truly a home away from home. The house is excellent. The host is amazing. Always willing to help in whatever way he can. Thank you very much for a wonderful stay.We will definitely stay with you again.
Superhost
Home in Kissimmee
4.89 out of 5 average rating, 27 reviews

Pelican House

JessicaRating, 5 stars3 months 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, 9 reviews

Sunset Cove at Champions! Book this very private

TamiRating, 5 stars3 weeks ago
This lovely home was exactly as described. Located near the end of a gated street, but within 20 minutes of many restaurants. It also had the best selection of kitchen supplies and the nicest washer & dryer I’ve ever seen in a rental. Sue was a pleasure to work with!! We hope to return next year.
Guest favorite
Townhouse in Kissimmee
4.94 out of 5 average rating, 31 reviews

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

RandyRating, 5 stars2 weeks ago
My family enjoyed our week stay! Best sleep we’ve had in months. Clean space. Large eating area for entire family. Loved it . Booking agai this summer for sure
Guest favorite
Apartment in Kissimmee
4.91 out of 5 average rating, 108 reviews

Modern 3 Bedroom Apartment Near the Theme Parks

PatrycjaRating, 5 stars4 days ago
I recommend this place. It was easy to find, easy check-in. Host always responsed to my texts, even the silly ones :) The apartment is specious. It was very clean and had lots of towels.
Guest favorite
Home in Oviedo
4.9 out of 5 average rating, 29 reviews

Cozy Knight Haven

JulieRating, 5 stars1 month ago
This house was in perfect condition and in perfect proximity to UCF for our visit with our daughter. Extremely clean. We would definitely stay here again on our next visit and bring our dog with us next time!

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

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