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
A colorful hammock is suspended between two posts outside a green bungalow. The entrance features a cozy wooden door with warm lighting. A fenced catio can be seen nearby, providing a safe outdoor space. Lush greenery surrounds the area, enhancing the tranquil outdoor setting.
Home in Orlando
4.94 out of 5 average rating, 35 reviews

Pet-Friendly Bungalow Near Downtown Orlando

LisaRating, 5 stars1 week ago
Megan was really attentive and great to book with! The house felt very comfortable, like I was staying at a good friend’s house for a few days. I loved being so close to downtown and really appreciated the pet friendly hospitality as well!
Guest favorite
Home in Orlando
4.97 out of 5 average rating, 118 reviews

Modern 3/2 in Ivanhoe Village

DanRating, 5 stars2 weeks ago
2 couples and an adult child stayed here for 2 days in April. Everything was as expected, and the location was great for what we needed (very close to wedding venue). Host communicated clearly and thoroughly. Check-in time is precise - we arrived about 10 minutes early, and could unlock the door at exactly 3pm! Beds were comfortable, kitchen had enough silverware and storage for our needs, bathrooms had plenty of towels, and there was lots of other space for us to work a bit (ugh) and relax. Overall a great location and value for us. Thanks!!
Top guest favorite
The exterior of the villa showcases a well-maintained façade with siding in soft gray tones. A golf cart is parked on the driveway, alongside a neatly landscaped area featuring rose bushes. The front entry is framed by two accent lights and features an inviting porch.
Home in The Villages
5 out of 5 average rating, 29 reviews

SpringHouse - 3 Bdrm Patio Villa in The Villages

RachelRating, 5 stars2 weeks ago
Walt was a fantastic host. His house was amazing. Very clean, well stocked with thoughtful items, extremely comfortable and Walt was amazing about helping with questions and giving us things to do in the area. I have never stayed at a nicer or more thoughtful Air Bnb. We will definitely be planning to come back.
Top guest favorite
A spacious living area is displayed, featuring a sectional sofa and a large wall-mounted TV. The open kitchen showcases modern appliances and a dining table for six. Natural light floods the space through sliding glass doors that lead to the backyard.
Home in Orlando
4.97 out of 5 average rating, 122 reviews

Beautiful House Completely Remodeled

MichaelRating, 5 stars1 week ago
Jonny's place was lovely. He clearly puts a lot of effort into it. He was extremely helpful, responding to questions almost immediately. My family and I would be happy to stay there again and we highly recommend him.
Superhost
A serene outdoor area features a sparkling pool surrounded by a paved patio. Two gazebos provide shaded seating options, complemented by a few lounge chairs and decorative planters. The fenced yard offers privacy, and the space invites relaxation and gatherings.
Home in Winter Park
5 out of 5 average rating, 5 reviews

Casa Winter Park

ElisaRating, 5 stars3 months ago
We had a wonderful stay! We came down to celebrate our daughter’s engagement and Juan accommodated us early and was very helpful! It was a wonderful place and it worked perfectly to gather together with family. We had a small celebration after the engagement and the house had plenty of dishes to use for food and the ambiance was great- piano, fireplace, nice big table for laying out food. We also loved the backyard but it was too cold to use the pool or fire pit, but still lovely features. It was wonderful that each bedroom had their own en suite bathroom..no fighting over who would get the best room! The house was clean, cozy and comfortable. The neighbors concerned me a little, but we felt safe. The road out front was a bit noisy but it’s also very close to Publix and other shopping which was great. Overal,l we would recommend staying there.. it was a wonderful experience!
Guest favorite
A spacious living area features a comfortable gray sectional sofa adorned with a warm throw. A cozy area rug lies beneath a glass coffee table. The open layout includes a dining area visible in the background, with stylish furnishings and natural light coming through the windows.
Home in Orlando
5 out of 5 average rating, 5 reviews

Corporate Downtown Luxury Rental

NicholeRating, 5 stars4 months ago
This home was lovely and perfect for me for a couple weeks. It's in a relatively quiet area, albeit close to a main road, but still pretty neighborhoody, with a park down the street. Easy access to grocery stores, quick serve restaurants and a couple casual dining spots, and 5 mins from downtown/15-20 mins from Winter Park. The house itself was very functional, the kitchen is well equipped and living area is cozy. Closet space is a bit limited and it might be tight for more than one person for too long, but it was just what I needed while in town for business. The owners were very responsive and friendly, and when I needed help with a small issue were quick to address. Definitely would recommend.
Guest favorite
Home in Clear Lake
4.93 out of 5 average rating, 447 reviews

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

KerryRating, 5 stars1 week ago
Great stay, close to Universal Studios, was able to stay with my family last minute and nice private backyard. House was clean and easy to find. The washer and dryer were a plus and the home was cute and cozy. Would recommend to anyone visiting Orlando or surrounding areas.
Top guest favorite
A spacious living room features a green sectional sofa, a striped area rug, and a round pendant light hanging from the ceiling. Large windows allow natural light to fill the space, and a small dog stands on the floor by the sofa, adding a welcoming touch.
Home in Sanford
4.96 out of 5 average rating, 23 reviews

Mid-Century Modern Dwelling

AriannaRating, 5 stars1 week ago
Stayed here for my cousins wedding. It was a great place to stay. My dog enjoyed the backyard and the house was very nice. Would be a place we would stay again if needed!

Pet-friendly home rentals with a pool

Guest favorite
The in-ground swimming pool, shaped in a natural curve, is surrounded by a red deck and lush greenery. Pool toys and a basketball hoop are visible, alongside lounge chairs, providing space for relaxation and enjoyment.
Home in Orlando
4.88 out of 5 average rating, 118 reviews

3 BR/2BA Home w Private Pool~12 min to Airport!

Jordan MatthewRating, 5 stars2 weeks ago
Great place to stay at. Lots to do. Host was helpful
Superhost
Home in Davenport
4.6 out of 5 average rating, 10 reviews

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

BetsyRating, 5 stars1 week ago
We just left after staying for 12 days and it definitely felt right at home. Monique was always very responsive and even came to bring a pack and play and high chair for my grandson. Any concern I had, it was answered and taken care of. I would recommend this place.
Top guest favorite
A welcoming living area features a brown leather sofa adorned with a plaid throw and decorative pillows. A wooden coffee table sits in front, complemented by a woven rug. Artful accents are displayed on the floor along with a minimalist ladder shelf.
Home in Orlando
5 out of 5 average rating, 126 reviews

Private pool home near Downtown

JessicaRating, 5 stars1 week ago
This is instantly become my favorite Airbnb. Such a wonderful and beautiful experience. It’s an absolutely fantastic location while also enjoying the aspect of privacy. This will definitely be my go to anytime that I have to come into Orlando!
Top guest favorite
A swimming pool is surrounded by a spacious deck with lounge chairs. A pool house is visible in the background, featuring large glass doors that open to the outdoor space. Lush greenery and palm trees enhance the inviting atmosphere of the backyard.
Guesthouse in College Park
4.97 out of 5 average rating, 75 reviews

Amazing New Pool House!

ThomasRating, 5 stars1 week ago
Dave and Nadia were very accommodating. Quick response to any of our requests. Great location. Nice quiet neighborhood. Walkable to numerous dining options.
Guest favorite
Townhouse in Orlando
4.71 out of 5 average rating, 117 reviews

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

RichardRating, 5 stars4 days ago
amazing communication, beautiful property, cant wait to reutrn.
Superhost
An aerial view displays a single-story home surrounded by green lawns and trees. Neighboring properties feature screened-in pools. A clear driveway leads to the entrance, providing a sense of space and accessibility. The quiet neighborhood setting is evident in the layout.
Home in Davenport
4.81 out of 5 average rating, 180 reviews

4BR-2KingMasters-SpaHeat-Private Pool-Remodeled

LaylaRating, 5 stars2 weeks ago
Tetyana’s place was very clean, welcoming, and felt like home away from home. It was conveniently located near Disney and easy to access. The bed was very comfortable and I slept like a baby. The master bath was a great way to unwind and relax after walking over 10,000 steps at the Disney parks. We LOVED the jacuzzi/pool combo and how secluded it was. Very quiet neighborhood, responsive host, and easy check-in. We’ll be back. :)
Superhost
Townhouse in Kissimmee
4.81 out of 5 average rating, 134 reviews

T7674O/Windsor Hills Resort/3Bedrm/2miles Disney

MiriamRating, 5 stars1 week ago
Had a great stay! Perfect location, we enjoyed the community pool! Host responded fast when I had questions and the place was extremely cute! Pictures match exactly!
Superhost
The master bedroom is presented with an orange accent wall and a spacious bed. Natural light enters through a nearby window, highlighting the inviting atmosphere. A stylish chair is positioned next to the window, offering a cozy reading nook.
Home in Davenport
5 out of 5 average rating, 3 reviews

Spacious Home w/ Pool&Resort Amenities,near Disney

NelyRating, 5 stars3 weeks ago
I want to start thanking Alex and Luis becouse they was so nice with us. We enjoyed stay in their property and if we had any question they response very quickly. We are 100% sure that will go back to this place. I recommend this place with out doubt. thank you

Private, pet-friendly home rentals

Top guest favorite
A single-family home with a brick facade is surrounded by lush green grass. The property features a spacious driveway leading to a garage. Large windows allow for natural light, and a charming front porch area is furnished with seating options under the shaded trees.
Home in Orlando
4.93 out of 5 average rating, 100 reviews

24/7 HomeCare Group

BinuRating, 5 stars1 day ago
Positives: The house is located in quiet neighborhood. It was clean and well organized. It was easy to communicate with Edna and she was very responsive. Negatives: The house is old and needs some TLC, one of the kitchen cabinet doors was falling off and the door to the backyard also needs repair.
Superhost
A corner near the staircase features a serene arrangement of potted plants nestled among smooth white pebbles. The plants vary in height and shape, adding a natural element to the space. Light filters in, highlighting the greenery against the light-colored walls.
Tiny home in Altamonte Springs
4.87 out of 5 average rating, 67 reviews

The Tiny Cottage in the Springs/ Central FL

ArianaRating, 5 stars4 weeks ago
Perfect for a short term stay, comfy bed and nice size shower and good kitchen. Super close to Winter Park with all of its fun stuff to do. Nice promise entry and quiet location. Albia the host is very sweet and friendly, and responds quickly.
Top guest favorite
The living area features a modern design with sleek white tiles and a stylish light fixture. A glass coffee table sits in front of a comfortable sofa, while the fully equipped kitchen with bar seating is visible in the background, complemented by a contemporary color palette.
Townhouse in Clermont
4.97 out of 5 average rating, 76 reviews

The silver cottage

AshleyRating, 5 stars3 weeks ago
Vanessa’s place was amazing as always. Location is very convenient and close to historic downtown. The house is cozy and has a large backyard. Really enjoyed our stay.
Guest favorite
A vibrant children's bedroom featuring a blue color scheme, highlighted by superhero murals on the walls. A double bunk bed is positioned against the far wall, while a sleek dresser and television are visible in the room. A circular ceiling light emits a soft glow.
Villa in Davenport
5 out of 5 average rating, 21 reviews

Disney Proximity: Luxury 5BD Home

NichelleRating, 5 stars1 week ago
We were very pleased with our stay it was comfortable and convenient to all the places we went to visit.
Superhost
The exterior of a single-story home is visible, featuring a well-maintained lawn and landscaped garden. The façade is painted in light colors with a central entrance highlighted by a blue door. A car is parked on the driveway, which leads to a two-car garage.
Home in Kissimmee
4.89 out of 5 average rating, 28 reviews

Pelican House

WilliamRating, 5 stars2 weeks ago
We stayed at the Pelican House for three whole months. This home worked well for our extended stay because of its proximity to restaurants, groceries and Disney World! The neighborhood was quiet pretty much every night and having the open green space in the back was really nice, especially when the Sandhill Cranes came by in the mornings. They were awesome to watch. Donna was very responsive to any questions or concerns we had during the stay. She would reply within 10 minutes usually. The biggest benefit for us was proximity to Disney World. We could leave the house and be at the parks within 15-20 minutes most days. Traffic coming back from Disney was typically a challenge, though I feel the whole area in Kissimmee would be the same. All in all, we would absolutely stay at the Pelican house again for any future long-term stay in that area. It worked great for our needs this trip! Thanks Donna!!
Guest favorite
An outdoor dining area is set with a glass table surrounded by six cushioned chairs. Pink and yellow plates are displayed on the table, complemented by a vase of fresh flowers. A cozy bedroom is visible through the sliding glass doors, adding a tranquil touch to the space.
Home in Clermont
5 out of 5 average rating, 9 reviews

Sunset Cove at Champions! Book this very private

TamiRating, 5 stars1 month 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
A comfortable sleeping area features a spacious bed with neatly arranged bedding and a decorative pillow. A cozy sofa is positioned nearby, adorned with colorful cushions. A television is mounted on the wall, providing entertainment options.
Apartment in Orlando
4.91 out of 5 average rating, 57 reviews

D&D’s Private Orlando Loft w fenced backyard!

AleksandrRating, 5 stars5 days ago
Great neighborhood, lots of shops, parks nearby. There is everything for everyday life, clean, well-groomed and comfortable! Thank you very much, we liked it very much! I recommend
Guest favorite
A playful scene features a dinosaur costume clad in a checkered apron and chef's hat, kneeling beside an open oven. Colorful cookies are placed on a paper towel on the oven's rack, adding a whimsical touch to the kitchen setting.
Home in Orlando
4.91 out of 5 average rating, 208 reviews

★ PRIVATE HOME IN DOWNTOWN ORLANDO ★ RETREAT ★

HaileyRating, 5 stars2 weeks ago
Andy’s place was a great dog-friendly house in an ideal location! It’s right in the middle of town, close to everything, but surprisingly quiet—you’d never guess how close the traffic is when you’re in the neighborhood. It was also a quick and pleasant drive to Universal. Nice little park a couple blocks down. We had a great time and would gladly stay here 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

    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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