Pet-friendly holiday rentals in Winter Garden

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Winter Garden

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Superhost

Tiny home in Orlando

4.84 out of 5 average rating, 305 reviews

The Blue Heron 6 Month Lakefront Tiny House Rental

The Blue Heron was the 8th tiny home to join our community in Orlando, Florida in 2018. You'll find this inviting accommodation steps from Lake Fairview and it can accommodate up to 4 guests. There is a queen-size bed in the lofted bedroom, in addition to a sofa bed in the living room area. A fully equipped kitchen and modern bathroom will keep you feeling at home, but you’ll likely want to spend the majority of your stay on the wide, wooden deck relaxing and enjoying the scenery. During your stay, take advantage of Florida lake life! We encourage all guests to take advantage our FREE kayaks and paddle board rentals as well as our yard games, hammocks, fire pit, propane grill, volleyball, cornhole and fishing gear upon request. Turn your tiny home experience into big fun on the lake! **This tiny house is not pet friendly**

Top Guest favourite

Home in Orlando

4.93 out of 5 average rating, 105 reviews

24/7 HomeCare Group

Bring the whole family to this great place with lots of room for fun. Pets are family too! Master bedroom w/king bed, tv, separate bath, walk in closet, and sitting area. Second bedroom with queen bed and tv. Third bedroom with queen bed and tv. Fourth room with sleeper sofa perfect for the kiddos. Dedicated office/work space for when duty calls! Living room with huge comfy sofas, decorative fire place, tv. Backporch/patio with grill and plenty of seating. Completely fenced-in backyard.

Top Guest favourite

Home in Minneola

4.98 out of 5 average rating, 130 reviews

Pool + Heated spa Family friendly King suite Oasis

Welcome to your perfect Florida getaway! This beautifully updated 3-bedroom, 2-bath home in Minneola offers everything you need for a relaxing and fun-filled stay. Whether you're traveling with family, friends, or pets, this home is designed to make you feel right at home. Step outside to your private backyard oasis featuring a sparkling pool, hot tub, and serene views overlooking a peaceful pond. Fire up the grill, unwind under the market lights, or soak up the sun with your favorite drink.

Guest favourite

Home in Apopka

4.87 out of 5 average rating, 151 reviews

Country Pool home on 2 acres-30 minutes to Disney

Relax with friends and family at this country pool home just northwest of Orlando and all of the attractions! 30 minutes to Disney and Universal Studios. 10 minutes to Historic Mount Dora. 8 minutes to Kelly Park/Rock Springs Run. One hour to Daytona Beach. What a great location and place to stay to explore Central Florida! Pets are welcome! 3 queen beds & couch **The hot tub you might see in a photo is not advertised because it is not operational. The pool is very refreshing but not heated.

Top Guest favourite

Guest suite in College Park

4.96 out of 5 average rating, 189 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

Home in Winter Garden

4.91 out of 5 average rating, 204 reviews

Cozy Winter Garden Home 20 MINUTES FROM DISNEY

Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

Top Guest favourite

Home in Minneola

4.98 out of 5 average rating, 162 reviews

Spacious Getaway ~ Heated LED Pool & Ping Pong

Welcome to your Spacious Getaway! Exterior Features: ★ LED Lights in Pool and on Pool Cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ Ping Pong Table ★Large Shower in Master Bathroom ★ROKU on each TV Extras: ★ Heated Pool up to 95 Degrees - $40 per day (Pool Water is normally at 75 degrees without the Pool Heater) ⚠️ Pet-Friendly, but the pet must be added to the reservation ($75 Pet fee)⚠️ {Willing to Negotiate Monthly Prices}

Guest favourite

Tiny home in Clermont

4.93 out of 5 average rating, 102 reviews

Pet Friendly, Modern Tiny House in Clermont

This stylish tiny house is perfect for a short or mid-term rental, featuring 2 lofts with twin beds, a queen bed on the main floor, a full bathroom with a large rain-head shower, and a gorgeous kitchen with full-size appliances. Enjoy a 7-foot projector screen that doubles as a TV and privacy divider, plus a lovely outdoor area with a gazebo, table, grill, and another TV ideal for experiencing tiny living in luxury with plenty of space. Also, check airbnb.com/h/tinyhamptonsjitney

Top Guest favourite

Guesthouse in Orlando

4.98 out of 5 average rating, 105 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 sports a full kitchen, king sized bed, 2 firm king pillows, 2 soft king pillows, 100% cotton sheets and coverlet. Soap, shampoo/conditioner, laundry detergent, and dish soap are provided.

Top Guest favourite

Apartment in Bay Lake

4.97 out of 5 average rating, 102 reviews

Cozy 2Bed Boho Hideaway 10 Min to Parks Allows Pet

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 8 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Top Guest favourite

Guesthouse in Windermere

4.94 out of 5 average rating, 270 reviews

Paradise nook near Orlando's theme parks

A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

Guest favourite

Guest suite in Orlando

4.89 out of 5 average rating, 118 reviews

Modern Studio, FL Mall, Airport, Universal Studio

Welcome to Orlando, the City Beautiful! Unwind in this clean, private studio near the Florida Mall and top attractions. Enjoy your own separate entrance and private bathroom for a comfortable stay. Essentials like fresh towels, soap, and more are provided. Whether you're here for business or leisure, you'll be just minutes from Orlando’s world-famous destinations. We look forward to hosting you!