Pet-friendly holiday rentals in Winter Garden

4.97 out of 5 average rating, 400 reviews

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

Condo in Orlando

Waterfront 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 beautiful pool that offers a full Tiki bar and 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, 111 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, 158 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.

4.94 out of 5 average rating, 210 reviews

A bright and spacious area features a white bed and a stylish brown sofa. Modern decor is complemented by natural elements, including a potted plant. A wall-mounted television and a wooden coffee table enhance the inviting environment.

Guest suite in Kissimmee

temple & A/C glamping under a 120 y/o oak tree

How this Airbnb was born? We wanted to create a space to enhanced our soul, power our mind, fuel ourselves, to meditate, to create ideas, to be a part from the world, The Temple. Glamorous Camping idea came across, oh my!, once you go inside this tent, you don't want to come out. Be present. Friends and family started asking, can I stayed?, day by day closer people want it to live this experience and more positive comments we were getting, so we decided, why don't let others try it? Welcome

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.

4.97 out of 5 average rating, 232 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, 116 reviews

Guesthouse 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!

Guesthouse 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, 119 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.

Apartment 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.

4.96 out of 5 average rating, 135 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.

4.94 out of 5 average rating, 275 reviews

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.

Guesthouse in Windermere

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

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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.

4.97 out of 5 average rating, 147 reviews

Beautiful House Completely Remodeled

4.93 out of 5 average rating, 145 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

5 out of 5 average rating, 156 reviews

Orlando Cactus House! 5min from Universal Studios

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.

4.97 out of 5 average rating, 155 reviews

Private pool home near Downtown

4.97 out of 5 average rating, 130 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

A spacious living area features light-colored wooden flooring and large windows allowing natural light to fill the space. Two comfortable sofas are arranged around a glass coffee table, and a potted plant adds a touch of greenery. A dining table is visible in the background.

5 out of 5 average rating, 132 reviews

Stay in the best neighborhood in downtown Orlando!

An outdoor space features a heated pool and a hot tub, surrounded by stone masonry. A custom bar, crafted from wood, is visible alongside tropical plants. Two built-in TVs are fitted above the bar area, enhancing the outdoor living experience.

4.9 out of 5 average rating, 145 reviews

Stunning Orlando Getaway w/Spa & Heated Pool

4.95 out of 5 average rating, 127 reviews

A private outdoor area features a pool with a spa, surrounded by a spacious deck. A basketball hoop is positioned nearby. A large inflatable swan floats in the water, while a hammock provides a cozy spot for relaxation. Lush greenery frames the scene under a colorful sky.

Home in Kissimmee

Luxury Encore Pool Spa Pets Game Rm Theater Gym

Pet-friendly home rentals with a pool

4.83 out of 5 average rating, 107 reviews

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

Lovely Winter Park Home close to Hospitals !

4.93 out of 5 average rating, 30 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

4.86 out of 5 average rating, 101 reviews

A warm living space features a dark wooden ceiling and an accent wall with textured concrete. Comfortable seating faces a mounted television, while wooden shelves are adorned with books and decorative plants. Natural light enters through large windows, enhancing the inviting atmosphere.

Condo in Orlando

5 mins Universal 10 mins Epic park | Rustic LOFT

4.89 out of 5 average rating, 89 reviews

Condo in Davenport

Luxurious Living 15 minutes from Disney

4.95 out of 5 average rating, 147 reviews

A spacious living area features a large sectional sofa arranged around a round coffee table. Bright lights illuminate a modern kitchen equipped with white cabinetry and an island with seating. A ceiling fan is suspended above, enhancing the airy ambiance.

Townhouse in Davenport

Stylish Stay in Davenport

5 out of 5 average rating, 7 reviews

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.

Townhouse in Kissimmee

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

4.99 out of 5 average rating, 85 reviews

A hot tub is situated on a patio with a view of a lake at sunset. The vibrant sky features hues of orange, pink, and purple, while a railing surrounds the space, enhancing the scenic atmosphere. The tranquil water reflects the colors of the sky.

Cottage in Kissimmee

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

4.94 out of 5 average rating, 68 reviews

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

Palms and Paradise

Private, pet-friendly home rentals

4.88 out of 5 average rating, 17 reviews

A serene view of the lake at sunrise, with the water reflecting soft hues. Silhouetted cypress trees surround the scene, draped in moss. A private dock extends over the calm water, leading to a boathouse, while a gently waving American flag adds a sense of tranquility.

Home in Clermont

Secluded lake front w/ private dock and boat lift

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.

Apartment in Clermont

Relaxing 1-Bedroom Farm Retreat. Pets welcome!

4.92 out of 5 average rating, 26 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

4.95 out of 5 average rating, 43 reviews

A spacious living area features comfortable seating arrangements with a light-colored sofa and accent chairs. Natural light floods in through large glass doors, leading to a view of the outdoor space. A round coffee table occupies the center, complemented by decorative elements.

Home in Ocoee

Cozy home near Disney with a king size bed

5 out of 5 average rating, 41 reviews

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

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

4.71 out of 5 average rating, 7 reviews

A modern kitchen is showcased, featuring stainless steel appliances, including a refrigerator and oven. Bright white cabinetry contrasts with the light wood flooring. A spacious countertop offers ample workspace, while a sliding door provides natural light and access to the outdoors.

Home in Windermere

Beautiful Comfort & Convenience

4.89 out of 5 average rating, 85 reviews

The living area features light blue walls and wooden flooring, with large windows providing views of the lake. Soft gray couches are complemented by teal accents. A round coffee table sits at the center, and elegant window treatments frame the inviting natural light.

Home in Clermont

Lake view home near Downtown newly remodeled.