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 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
4.96 out of 5 average rating, 130 reviews

Beautiful House Completely Remodeled

AnnaRating, 5 stars6 days ago
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!
Guest favorite
A light-filled living area features two inviting sofas arranged around a glass coffee table. A vibrant blue area rug adds color to the floor. The open layout connects to a dining space with a round table and sleek black chairs, creating a relaxed atmosphere.
Home in Clermont
4.93 out of 5 average rating, 211 reviews

Beautiful house in Orlando/heated pool/Disney

KrystalRating, 5 stars2 weeks ago
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!
Top guest favorite
A spacious private pool is enclosed by a screened structure, featuring a basketball hoop at one end. The crystal-clear water is surrounded by a concrete deck, while colorful flags decorate the fencing, adding a friendly vibe to the outdoor space.
Home in Orlando
4.99 out of 5 average rating, 135 reviews

Private pool home near Downtown

VanRating, 5 stars3 weeks ago
Great house. Great host. Always attentive and responsive. 2nd stay. Will go for a 3rd
Guest favorite
The living area features a leather sofa and a stone fireplace as a focal point, complemented by a ceiling fan and natural light. A decorative mirror hangs on the wall above a console table, and the space connects to an updated kitchen visible through an open doorway.
Home in Orlando
4.93 out of 5 average rating, 183 reviews

The Orlando Retreat.

NisiRating, 5 stars6 days ago
My family and I stayed here for a few days in we generally enjoyed our stay. The bonus was that it was pet friendly and the pool was a nice touch! It being close to the road did not bother us, we actually really didn’t hear any noise everyone slept peacefully. My dog loved the yard. Everything was comfortable. Universal was only like 20mins away so the back the forth wasn’t an issue. Thank you again!
Guest favorite
A large, inviting pool glistens under the sun, surrounded by a spacious patio and palm trees. A stylish, shaded cabana is positioned nearby, offering a retreat for relaxation. The pool area is enclosed and features a clean white fence, enhancing the tranquil outdoor atmosphere.
Home in Orlando
4.88 out of 5 average rating, 203 reviews

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

WadeRating, 5 stars4 days ago
The place was amazing! The private pool and hot tub were exactly what we needed during a week of visiting theme parks. The backyard is so relaxing. Shopping and dining is very close as are the Universal parks and the airport. You can't beat the location! Would definitely stay here again! Thanks for a great stay!
Guest favorite
The exterior of a two-story Spanish Mission-style home is depicted in soft twilight. The structure features arched entryways with large windows, surrounded by lush landscaping. A decorative lantern illuminates the front entrance, enhancing the inviting charm of the property.
Home in Delaney Park
4.89 out of 5 average rating, 147 reviews

3,000 Sqft Historic Home With Pool Near Everything

Alyssa MaeRating, 5 stars1 week ago
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!
Superhost
A cozy living area is highlighted by a decorative wall, a TV mounted above a light-colored cabinet, and a plush seating arrangement. A fire pit with glowing embers is visible, providing a warm ambiance. A game table with two chairs and a pool table is present, alongside a screened pool area showcasing a sunset view.
Home in Kissimmee
4.87 out of 5 average rating, 190 reviews

Waterfront retreat,KING Bed,Heated Pool & Fire Pit

BriannaRating, 5 stars1 month ago
We had an amazing stay! The place was beautiful and in a nice neighborhood. The amenities were perfect for a family trip with kids so they weren’t bored at all. Lots of fun to be had here! Will definitely recommend!
Guest favorite
A spacious living area features a comfortable brown leather couch and a matching armchair, positioned on a colorful geometric area rug. A wooden coffee table sits in front, and a large flat-screen TV is mounted on the accent wall, complemented by a ceiling fan above.
Home in Orlando
4.91 out of 5 average rating, 159 reviews

SODO Mid Century Modern Cottage

GwynethRating, 5 stars1 week ago
The place was very impressive and clean. The place was very easy to find. Close to down town and was very near to the grocery. The neighborhood was very quiet. The kitchen was well stocked, there was even coffee and tea there for us to use in the next morning as well as during the tine we were there. The place felt like home. The beds were very comfortable. The bathroom was stocked as well. The owners take a great pride in how the place is kept . Would go back there again.

Pet-friendly home rentals with a pool

Guest favorite
The private swimming pool is enclosed within a screened-in patio, featuring a hot tub adjacent to it. A pink inflatable flamingo and a beach ball float in the clear water, while two comfortable lounge chairs are positioned nearby, ideal for relaxation.
Home in Clermont
4.88 out of 5 average rating, 17 reviews

Comfy 4BR near Disney/pool and Hottub

MadelaineRating, 5 stars1 month ago
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.
Top guest favorite
A comfortable game room is designed for relaxation and entertainment, featuring a large sectional sofa in warm tones with decorative pillows. A foosball table is positioned prominently, while playful wall art adds character to the space. Natural light filters in through a window with a gentle window treatment.
Home in Davenport
4.98 out of 5 average rating, 66 reviews

Near Disney Fun: Golf Retreat, Pool & Private Spa

JessicaRating, 5 stars2 weeks ago
Kimberly was a delightful host. She was very responsive when we had any questions. Her home felt very cozy and comfortable. She made it so easy to check in and accommodating. My family and I went to Disney for 4 days and it felt nice to be away from the traffic and it was easy to get to the parks. The kids loved having a pool to themselves to enjoy after a long day at the parks. There is also a grocery store, Starbucks and plenty of places to eat nearby, which made things very convenient for my family. I would definitely rebook Kimberly’s home again in the future and highly recommend if you are looking for a home away from home.
Guest favorite
The living area features a light-colored sofa adorned with decorative pillows, arranged around a coffee table. Natural light is provided by two windows, complemented by sheer curtains. A wall-mounted artwork adds color to the space, while a rug softly anchors the seating arrangement.
Home in Winter Garden
5 out of 5 average rating, 14 reviews

Entire clean comfortable house

GregoryRating, 5 stars1 month ago
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.
Superhost
A living room is furnished with a light grey sofa and a matching armchair, offering ample seating. Two coffee tables are positioned centrally on a patterned area rug. Artistic wall decor and warm lighting create a relaxed ambiance, with a dining area visible in the background.
Townhouse in Kissimmee
4.71 out of 5 average rating, 167 reviews

Cozy Townhouse in Kissimmee, near Orlando!

LynnRating, 5 stars2 months ago
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.
Superhost
A modern kitchen is displayed, featuring sleek black and white cabinetry with gold handles. Stainless steel appliances, including a refrigerator and microwave, are visible. The countertop is organized with kitchen essentials, and a patterned backsplash adds visual interest, complemented by a rug placed in front of the sink.
Apartment in Clermont
4.81 out of 5 average rating, 16 reviews

Modern 2B/2B Villa Near Disney

LexiRating, 5 stars1 week ago
Had an extended stay here and it was perfect! The neighborhood is quiet and has great amenities. Short walk to lake louisa as well and is close to shopping. The unit is well kept and had everything I needed for my stay! Jessica and her husband responded quickly and answered all my questions. I appreciated their tentativeness!! Will stay here again if I get the opportunity!
Top guest favorite
The private pool area features a small splash pool surrounded by a protective fence, with two lounge chairs and a circular table adorned with a potted plant. Sunlight fills the space, creating a bright and inviting atmosphere.
Townhouse in Clermont
4.93 out of 5 average rating, 122 reviews

Modern Retreat close to Disney - King Beds, Pool

HeatherRating, 5 stars5 days ago
This is a beautiful and spacious place to stay. It’s in a quiet neighborhood and has lots of places to walk. We would definitely recommend staying here!
Guest favorite
A tranquil outdoor space features a private pool surrounded by light-colored stone tiles. Lush greenery and vibrant pink flowers add color to the scene. Multiple lounge chairs are positioned nearby, providing options for relaxation in a peaceful setting.
Apartment in Winter Park
4.96 out of 5 average rating, 214 reviews

Apt C -Modern Elegance in the Heart of Winter Park

KarlaRating, 5 stars3 months ago
Really enjoying the place. Very nice and homey. The place was very accommodating and more. Provided more than the normal Airbnb. My parents & I had a great time.
Guest favorite
A modern two-story townhouse is presented, featuring a neatly arranged exterior with orange accents. Each unit showcases a covered patio area with seating, framed by landscaped greenery. A paved path leads to the front door, with designated parking spaces visible in the foreground.
Townhouse in Kissimmee
4.88 out of 5 average rating, 100 reviews

Themed rooms - gated community

CortneyRating, 5 stars1 week ago
Amazing host, communicated throughout my trip, answered all my questions and concerns, the home looks exactly like the photos, cleaning was superb, there was nothing to complain about. The home helped make my trip be even better and I will definitely book with them again and again, felt like home. 10/10 stars!!🫶🏽🫶🏽

Private, pet-friendly home rentals

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
4.96 out of 5 average rating, 82 reviews

The silver cottage

NicoleRating, 5 stars2 weeks ago
Thank you, Vanessa. Your charming little "cottage" was just perfect for us! It was clean, comfortable and convenient to everything we needed during our visit to Clermont.
Guest favorite
The exterior of the cottage features a simple wooden deck leading to double glass doors. Lush greenery surrounds the entryway, enhancing the natural setting. The expansive lawn offers views of the lake in the background, creating a peaceful atmosphere.
Guesthouse in Clermont
4.97 out of 5 average rating, 30 reviews

Lake Front Luxury in Private Cottage

TimRating, 5 stars3 months ago
We loved our stay on the lake. Thank you:)
Guest favorite
The exterior of the home features a covered porch with seating, overlooking a sandy beach area and a clear lake. Two kayaks are positioned on the shoreline, with a grassy area leading to the water's edge. The surrounding landscape includes residential properties and trees in the background.
Home in Ocoee
4.91 out of 5 average rating, 74 reviews

Lakefront in West Orlando Florida

RobertRating, 5 stars1 month ago
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!
Guest favorite
A light-filled living area features a spacious sectional sofa adorned with colorful pillows. A central ottoman sits on a patterned area rug, supplemented by a decorative lamp on a small red table. Two windows provide a view to the outdoors.
Home in Winter Garden
4.78 out of 5 average rating, 73 reviews

Downtown Winter Garden Mid Century Hipster I Pets

SamanthaRating, 5 stars2 months ago
We had to find a place quickly due to an unexpected emergency, and this home turned out to be an absolute blessing. From the moment we arrived, we felt safe, comfortable, and truly cared for. The house was spotless, well-equipped, and thoughtfully prepared with everything we needed. It gave us peace of mind during a stressful time, and for that, we are beyond grateful. Communication was seamless, and every detail from check-in, it was handled with care and attention. It truly felt like a home away from home, and we can’t thank the host enough for providing such a perfect space during our time of need. Highly recommend to anyone—whether you’re traveling for pleasure or facing unexpected circumstances. This home delivers comfort, reliability, and warmth.
Guest favorite
A charming single-family home features a light beige exterior with a two-car garage. Lush green landscaping, including palm and ornamental trees, borders the driveway, contributing to a welcoming curb appeal. The spacious front yard is well-maintained, complemented by a clean concrete walkway.
Home in Apopka
4.94 out of 5 average rating, 49 reviews

Palms and Paradise

SteeveRating, 5 stars1 month ago
everything was exactly as described—clean, cozy, and thoughtfully prepared. The host was incredibly responsive and made check-in and check-out a breeze.
Top guest favorite
The exterior of the bungalow is surrounded by vibrant greenery, featuring classic window shutters and inviting textures. Elements indicating various amenities include icons for bicycle rentals, pet policy, kitchen accessibility, rental vehicles, and event approvals, enhancing the overall experience.
Home in College Park
5 out of 5 average rating, 12 reviews

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

DomineRating, 5 stars1 week 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 favorite
The historic boutique inn features a two-story structure with a wraparound porch and large windows. The exterior showcases a combination of warm yellow walls and a dark roof, surrounded by lush greenery and moss-draped trees, offering a serene and inviting atmosphere.
Villa in Oakland
4.91 out of 5 average rating, 53 reviews

Historic Oakland Manor House

CrystalRating, 5 stars3 months ago
Great house! Great hosts!
Guest favorite
The bedroom features a queen size bed with soft linens and accent pillows. A television is positioned on a wooden dresser, and a ceiling fan adds comfort. The room is illuminated by wall art above the bed and a bedside lamp, creating a relaxed ambiance.
Apartment in Orlando
4.92 out of 5 average rating, 13 reviews

CHIC Comfort, 1 BR Orlando Apt with Parking

LynnetteRating, 5 stars5 months ago
Roger is a great host. I extended my stay because the place is in an excellent location for me to visit friends and family. I recommend his place 100%.

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 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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