Pet-friendly holiday rentals in Winter Garden

5 out of 5 average rating, 155 reviews

Home in Orlando

Orlando Cactus House! 5min from Universal Studios

Get ready to enjoy and relax in our beautiful cozyhouse, completely renovated just 5 min from UNIVERSAL STUDIOS,This gem is part of a DUPLEX with independent entrances. it is perfect for a quiet and comfortable stay close to all the tourist attractions. Volcano Bay(7mint)Convention Center International Drive(15min) Epic Universe(15min) Sea World(17mint)/Aquatica(15mint) Kia Center (20mins) Orlando International Airport(21 min) Magic Kingdom(23 min) Our cozy house is in the center of EVERYTHING

4.98 out of 5 average rating, 211 reviews

A balcony view captures a vibrant sunset over Lake Bryan, with hues of pink and orange reflected on the water. Outdoor seating includes two chairs and a small round table, inviting relaxation while enjoying the scenic surroundings.

Apartment in Orlando

Lakefront Resort Condo near Disney & Universal

Located minutes from Disney World and Universal Studios you are right in the middle of all the action with Disney Springs, Islands of Adventure,Sea World, Magic Kingdom,Epcot, two major outlet malls, and many other attractions .This resort style condo features a balcony overlooking beautiful Lake Bryan ,a large heated pool next to a Tiki bar with drinks/food menu.Concierge services for Park tickets available. Free parking ,24hr security. Free HBO & Netflix .No deposit required and no extra fees.

4.97 out of 5 average rating, 108 reviews

A serene lakeside view is presented, featuring calm waters reflecting a gradient of soft colors during sunset. A wooden dock extends into the water, framed by lush greenery and grasses. The landscape conveys a tranquil setting, inviting moments of reflection in nature.

Home in Winter Garden

Waterfront EPIC views, Dock, wildlife Near Disney

Experience the stunning sunrise views over Lake Apopka from our newly refurbished, elegantly appointed 4-bedroom, 2.5-bath vacation home in Winter Garden, FL. This haven is close to Orlando's Universal Studios 20 min, Disney World 25 min) & shopping (Mall of Millenia, premium outlets 17 min) Modern amenities, spacious layout that promises relaxation and convenience making the perfect home for exploring all local attractions and enjoying Florida's natural beauty. Minutes from City Swimming Pool

4.98 out of 5 average rating, 142 reviews

Home in Minneola

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.

Tiny home in Howey-in-the-Hills

A tiny home is showcased with a grey exterior and a metal roof. Two wooden chairs are positioned on a grassy area in front, and flower pots add color near the entrance. Steps lead up to the front porch, providing access to the inviting interior.

4.96 out of 5 average rating, 153 reviews

Horse Farm- (2) Tiny Homes 33mi from Orlando

Rest & Relaxation at its finest! This Tiny Home is set to impress! Add on the natural beauty of the rolling hills of Howey, with some of Thee most impressive sunsets over the water & this becomes an Incredible Unique Stay! After sunset, enjoy a nice campfire in your firepit, as you STARGAZE into the night! This Tiny Home is fully equipped with ALL of your needs. Located on the back 3 acres of property, from which you will have your own Golf Cart to travel to/from our Designate Parking Area.

Guest suite in College Park

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.

4.96 out of 5 average rating, 226 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.

4.91 out of 5 average rating, 206 reviews

A small, white house is framed by vibrant greenery and colorful plants. The front door, painted blue, adds a pop of color, while large windows allow light to fill the space. A wooden deck leads up to the entrance, enhancing the welcoming appeal.

Home in Winter Garden

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.

4.98 out of 5 average rating, 113 reviews

Guest house in Clermont

Charming Downtown Apartment - Walk to Everything

Stay in the heart of historic downtown Clermont- steps from the lakefront, breweries, shops, & dining. This light-filled, stylish apartment above our garage offers cozy aesthetics, comfy beds, a double shower, two spacious bedrooms, and a smart TV. Thoughtfully stocked for a stress-free stay, with garage storage for your bikes or paddle gear upon request. More than a stay—we proudly offer a distinct Clermont experience. We hope you love our charming town just as much as we do!

Guest house in Wadeview Park

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.

4.98 out of 5 average rating, 115 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.

4.98 out of 5 average rating, 117 reviews

A modern living area features a vibrant red sofa and two gray armchairs, offering ample seating. A stylish coffee table sits centrally, complemented by a small plant centerpiece. A large television is positioned opposite the seating, with soft lighting from table lamps creating a welcoming ambiance.

Flat in Clermont

Modern Suite in the Heart of Downtown Clermont 101

Attention Triathletes! Brand-new, Modern Suite, "Heart" of Downtown Clermont. Steps to quaint downtown restaurants, shops, and local Breweries. Conveniently close to the Clermont/Minneola Trail, Host of the Prestigious Triathlons and the Waterfront Park. Unique location for athletes! See all Clermont has to offer including the National Training Center and enjoy close proximity to Walt Disney World, Sea World and International Drive. Only 30 Min. to Downtown Orlando.

4.95 out of 5 average rating, 131 reviews

A bright bedroom features a spacious bed with a plush headboard and soft linens. Natural light enters through two windows, illuminating the room. A round mirror is mounted on the wall above a minimalistic desk with a chair, adding functionality to the cozy space.

Home in College Park

Priv. Modern Cozy CP 1B/1Ba Suite near DT Orl & WP

Private & Comfortable 1 bd/ba suite in a 2021 townhome with front view windows, queen size bed, walk-in shower& private entrance. Equipped w/ ceiling and portable fans, Roku smart TV, mini fridge/freezer, microwave, and Keurig. Located in a safe, quiet, walkable neighborhood. 5 minutes of College Park shops, 10 minutes from downtown Orlando, 25 minutes to Universal Studios, 30 minutes to Orlando International Airport, & 40 minutes to Disney.

Guest house in Windermere

A charming guesthouse is nestled among lush tropical vegetation, surrounded by diverse greenery and tall trees. Sunlight filters through the leaves, casting dappled light on the exterior and patio area, creating a serene and inviting atmosphere.

4.94 out of 5 average rating, 274 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.

Popular amenities for Winter Garden pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.93 out of 5 average rating, 144 reviews

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

The Boho Jungalow - Private | HotTub I Downtown

Home in Colonialtown South

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.

4.98 out of 5 average rating, 150 reviews

Private pool home near Downtown

4.91 out of 5 average rating, 160 reviews

A serene pool area is featured, reflecting the clear blue sky and surrounding greenery. The pool is bordered by a tiled edge, with colorful plant life adding vibrancy. A covered patio with a picnic table sits in the background, offering a shaded relaxation area.

Home in Orlando

Modern Tropical House Heated Salt Pool

4.81 out of 5 average rating, 204 reviews

Home in Orlando

The Calm Green One | Cozy Downtown Stay

4.88 out of 5 average rating, 158 reviews

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 Lake Cherokee

3,000 Sqft Historic Home With Pool Near Everything

4.97 out of 5 average rating, 128 reviews

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

Spacious Home with Pool & Hot Tub near Downtown

4.97 out of 5 average rating, 113 reviews

A living area features a modern television displaying a virtual fireplace, paired with elegant wall art and a decorative plant. Below, a pool area is illuminated with soft purple lighting against a backdrop of warm string lights, creating a relaxed atmosphere.

Home in Kissimmee

Modern House with Private Pool Getaway Kissimmee

4.94 out of 5 average rating, 137 reviews

The exterior features a light blue structure complemented by a covered carport. A well-maintained lawn with decorative stones and shrubs adds to the inviting atmosphere. Large windows provide natural light into the living spaces.

Home in Kissimmee

Winter Villa in Florida by the Lakes

Pet-friendly home rentals with a pool

Apartment in Champions Gate

An aerial view of a resort pool area showcases a winding pool surrounded by lush palm trees and tropical landscaping. Lounge chairs are arranged along the poolside, with shaded cabanas nearby. The resort features a terracotta roof and is set against a backdrop of greenery.

4.86 out of 5 average rating, 285 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

4.93 out of 5 average rating, 27 reviews

A private pool area is featured with subtle lighting creating a serene atmosphere. The pool includes a hot tub nearby, both of which are enclosed by a full-screen patio. The tranquil waters reflect various colors, enhancing the inviting ambiance for relaxation.

Home in Clermont

Comfy 4BR near Disney/pool and Hottub

4.98 out of 5 average rating, 452 reviews

A fenced oasis-style backyard features a heated in-ground pool surrounded by lounge chairs and tropical plants. A sunshade provides comfort over the pool area, while an outdoor seating area with a gazebo can be seen in the background beneath the bright blue sky.

Guest suite in Orlando

Sunny Resort Style - Pool & central location ☀️

A private screened hot tub is featured in the foreground, surrounded by an inviting outdoor seating area with a table and chairs. Lush tropical plants enhance the atmosphere, while a large mirror reflects the vibrant orange wall and soft natural light from the spacious windows.

4.95 out of 5 average rating, 213 reviews

2 BR Harmony House at Regal Oaks Resort

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.

4.69 out of 5 average rating, 173 reviews

Cozy Townhouse in Kissimmee, near Orlando!

A large swimming pool is set within a landscaped area, featuring a gentle curve and surrounded by lounge chairs and umbrellas. A clubhouse with a tiled roof is visible in the background, contributing to the inviting atmosphere of the gated community.

4.99 out of 5 average rating, 118 reviews

Family friendly/Pet friendly Orlando paradise

Guest house in Southern Oaks

A bright living area is presented with vaulted ceilings and hardwood floors. Comfortable seating is arranged around a central coffee table, with soft lighting provided by table lamps. Natural light filters through the windows, illuminating the decor and creating a welcoming atmosphere.

4.84 out of 5 average rating, 108 reviews

Historic lakefront guesthouse

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.

4.9 out of 5 average rating, 116 reviews

Themed rooms - gated community

Private, pet-friendly home rentals

4.97 out of 5 average rating, 86 reviews

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

The silver cottage

A vibrant game room features colorful walls inspired by video game themes, including a prominent mural of familiar characters. An arcade machine and a TV are present for entertainment. A gray sofa is situated in the room, complemented by playful decor elements.

5 out of 5 average rating, 6 reviews

3BR Home Near Disney w/ Pool, Spa & Game Room

Superhost

A well-lit bedroom features a spacious bed adorned with a patterned blanket. The walls are painted in calming shades of blue, complemented by bright yellow accents. Two decorative plants are positioned on either side of the bed, while a window allows natural light to fill the room.

Home in Winter Garden

4.91 out of 5 average rating, 11 reviews

Your Enchanted Home Near Downtown Winter Garden

4.94 out of 5 average rating, 71 reviews

An open living room and kitchen area features comfortable seating on a dark sofa and a modern futon. A light fixture adds illumination to the space. A well-equipped kitchen is visible in the background, with wood cabinetry and a dining area near a window.

Flat in Clermont

Relaxing 1-Bedroom Farm Retreat. Pets welcome!

A private pool area is enclosed by a screened lanai, showcasing a clear, inviting pool surrounded by light pavers. Soft yellow walls and playful wall accents complement the space, with a few lounge chairs available for relaxation in the sun.

5 out of 5 average rating, 17 reviews

Pet Friendly Pool Home Very Close to Disney!

4.92 out of 5 average rating, 24 reviews

A bright, open living area is furnished with a deep blue sofa and two woven chairs. A wooden coffee table sits in the center, surrounded by decorative elements. Large windows provide views of the lush greenery outside, while a wall-mounted television complements the space.

Home in St. Cloud

2 BR Lake View off-grid Home

4.98 out of 5 average rating, 40 reviews

A vibrant sunset fills the sky with hues of orange, pink, and purple, casting a warm glow over the calm lake. Silhouettes of trees frame the scene, while electric lines stretch across the horizon, enhancing the tranquil waterfront view.

Home in Clermont

Grandma’s Getaway