Pet-friendly holiday rentals in Winter Park

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Winter Park

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.
Home in Lake Formosa
4.97 out of 5 average rating, 144 reviews

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

Top Guest favourite
A cozy bedroom showcases a queen bed with an orange floral duvet cover and matching pillows. Three pieces of wall art in soft hues are displayed above the headboard. A door leading to the private entrance is visible, providing easy access.
Apartment in College Park
4.93 out of 5 average rating, 299 reviews

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft studio- queen bed, workspace, kitchenette, large bathroom, private yard area & entrance. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. $20 pet fee No cleaning fee. Universal 11 mi Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando City Soccer 4.6 AdventHealth Orlando 0.6 mi Orlando Health, Arnold/Winnie Palmer 3.8 Rollins College 1.9

Guest favourite
The cozy sleeping area features a spacious bed adorned with luxurious cotton sheets and coordinating pillows. A rattan headboard complements the tropical-themed wallpaper. A small seating area with a brown couch and decorative pillows is visible, adding to the inviting atmosphere.
Home in College Park
4.93 out of 5 average rating, 160 reviews

The Boho Jungalow - Private | HotTub | Downtown

This relaxing 1 bed 1 bath space in Downtown Orlando boasts a lush fenced-in private yard, hot tub, and fully equipped kitchen. We pride our studio on comfort, wellness, and delicate attention to detail to experience the magic of a trendy space in the heart of Orlando. Enjoy brand-new remodeling, furnishings, and appliances. This is the back unit of a 2-unit property. We include: ✅50" TV ✅Luxury mattress ✅Fiber optic Wi-Fi ✅Decaf Coffee & Tea ✅Disney Plus, Hulu, Max, Netflix ✅ Free Parking

Top Guest favourite
The exterior of the two-story cottage is captured, showcasing a red and white color scheme with black shutters. Lush green landscaping and a well-maintained lawn surround the home, while a concrete driveway leads to a detached garage nearby. A white picket fence adds charm to the property.
Guesthouse in College Park
4.91 out of 5 average rating, 192 reviews

8th Green Cottage - A relaxing oasis in the city

The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located 5 minutes from downtown. Sitting on the historic 1924 Dubsdread golf course. Enjoy the great views, pleasant and quiet neighborhood all with easy access to everything Orlando has to offer. Location is key when traveling and the 8th Green Cottage delivers! Disney, Universal, and Sea World all within a straight shot down I4. Free play Arcade with 3500 games included in spare bedroom Pets are welcome and stay Free.

Top Guest favourite
A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.
Guest suite in College Park
4.97 out of 5 average rating, 268 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

Guest favourite
A living area is presented with a gray sectional sofa and a blue accent chair. The space is enhanced by a patterned area rug and a small coffee table made of wood. Light filters through window blinds, illuminating the room's cozy decor and shelves filled with books.
Home in Audubon Park
4.86 out of 5 average rating, 98 reviews

The Sunrise House

Welcome! Here we offer you a home that gives you access to all things Orlando. This cute bungalow has SO much to offer! Nestled in a quaint neighborhood, you can WALK to the local garden, charming markets, breweries, restaurants, and coffee shops of Audubon Park and Mills 50 District. If you want to explore further, Downtown Orlando and Historic Winter Park/Park Avenue are a short 5-minute drive away. Did we also mention that we are pet friendly? Bring your fur baby with you!

Guest favourite
A welcoming entrance is framed by a vibrant green leaf panel, with a cheerful sunflower decoration displaying the word 'WELCOME.' The surrounding area features a red fence and a light-colored door leading into the home.
Guest suite in Orlando
4.92 out of 5 average rating, 175 reviews

Grey House near Orlando Universal Parks

Your family will be close to everything when you stay at this centrally-located place. The neighborhood is located just 17 min from the MCO airport. Also Downtown Orlando will be only 10 min from your Airbnb and even more, you can also find UCF just 14 min away. Universal Studio, Volcano Bay, and Islands of Adventure Them Parks are only 20 min away. The Aquatic Park Sea World will find it 28 min away. And the amazing Disney Parks located 35 min away. Traffic is moderate.

Top Guest favourite
A spacious bedroom features a large bed with white bedding and decorative pillows. Two soft bedside lamps illuminate the area, complemented by a cozy armchair and a decorative bench at the foot of the bed. Exposed brick wall accents the room.
Guesthouse in Wadeview Park
4.98 out of 5 average rating, 125 reviews

The Cottage A Pet Friendly Guesthouse

Welcome to The Cottage! A pet friendly, super cute, and quiet studio apartment built in 2016, located above the detached garage behind my house. Pets always stay for free, and no additional cleaning fees are charged. Private self access is provided so you come and go as you please. The unit has a full kitchen, king sized bed, 4 pillows, 100% cotton sheets and coverlet. Laundry detergent and dish soap are provided. Trash is located on the west sideof the building.

Guest favourite
A welcoming living room features a comfortable dark sofa accented by yellow pillows. A wooden coffee table sits in front, complementing the beige rug beneath. A glass desk with a chair is positioned near a window, with natural light illuminating the space. A 'WELCOME HOME' sign adorns the wall.
Apartment in College Park
4.91 out of 5 average rating, 125 reviews

Getaway in comfort with a pool

This excellent apartment has been furnished to a great standard. It’s the ideal retreat for a laid back & up-scale stay, located close to the absolute heart of Orlando. The neighborhood is known for its 20th-century cottages, abundant green spaces and lakes. Get ready to get inspired! Very close to some fabulous sites. All in all, guaranteed enjoyment and relaxation. All-day long. Settle in by zoning out with the four of you in a professionally cleaned home.

Guest favourite
A cozy guest suite is displayed, featuring a spacious queen bed with a textured white coverlet. A kitchenette is visible, equipped with a refrigerator, microwave, and wall shelves. Light streams in from the ceiling fan overhead, illuminating the modern and inviting decor.
Guest suite in College Park
4.9 out of 5 average rating, 267 reviews

Luxury Suite Near Disney & Downtown Orlando

Come enjoy a cozy & newly-renovated private guest suite centrally located near Downtown Orlando. Features a full kitchen, spacious bathroom, & luxurious queen bed for a peaceful & enjoyable stay. Private entrance, driveway and front porch, and convenient self check-in. Perfectly located walking distance from restaurants, shopping, and parks in a safe and family-friendly neighborhood. Easy access to Downtown Orlando, Theme Parks, and Winter Park/Park Ave.

Guest favourite
A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.
Condo in Winter Park
4.84 out of 5 average rating, 113 reviews

Lovely Winter Park Home close to Hospitals !

Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.

Top Guest favourite
A modern pool house is featured, with large glass doors opening to a swimming pool. The exterior includes a tree emblem and a small seating area with a chair. Sun loungers are positioned near the pool, surrounded by lush grass and a wooden fence.
Guesthouse in College Park
4.98 out of 5 average rating, 100 reviews

Amazing New Pool House!

A great choice for both tourists and business travelers looking for great value. A swimming pool and backyard oasis just outside your door! Awesome location close to the best neighborhoods in Orlando. We just built this pool house with a fully private entrance (side gate around main house). Totally comfy 1-bedroom house sleeps up to 3 people. Full kitchen and luxurious bathroom. Friendly hosts look forward to sharing their backyard paradise with you.

Popular amenities for Winter Park pet-friendly home rentals

When is the best time to visit Winter Park?

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Avg. price$172 AUD$176 AUD$173 AUD$169 AUD$155 AUD$169 AUD$173 AUD$165 AUD$155 AUD$163 AUD$186 AUD$183 AUD
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Quick stats about holiday rentals that are pet-friendly in Winter Park

  • Total holiday rentals

    Explore 120 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $56 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,830 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Winter Park holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Park rentals

  • 4.8 Average rating

    Winter Park stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Winter Park's top spots, include Orlando Science Center, Harry P. Leu Gardens, and Orlando Museum of Art

Destinations to explore