Pet-friendly vacation rentals in Winter Garden

4.97 out of 5 average rating, 114 reviews

Home in Mount Dora

Beautiful Mount Dora Charmer with Lake Ola Views

Step back in time in this beautifully updated Mount Dora home filled w/ original charm & character of the 1960’s! The entire 3bed/2bath home is private, fully fenced & yours to enjoy! Wake up to birds singing, a breathtaking view of Lake Ola & cozy up by the Tennessee stone fireplace. Inspired by Mid century design w/ several pieces remaining from the original owner of 60 years! The back yard is a relaxing dream filled w/ incredible landscape including oak, powder puff, magnolia & tabulia trees.

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.

4.96 out of 5 average rating, 170 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

5 out of 5 average rating, 104 reviews

Home in Oak Ridge

Harmony | Heated Pool | 10 min Universal & Epic.

Welcome to Harmony House: We want to Be your Host in Orlando! Let us show you why you should book with us: 🏡 1800 ft2 ground floor house 🌇 Top Location 🎢10 Min Universal Studios 🎢13 Min Epic Universe 🏰 20 Min Magic Kingdom 🛍️20 MIn Disney Springs 📺 4 Smart TVs 🛜 Fast WIFI 🧑‍🍳 Fully equipped kitchen 💻 Dedicated work space 🅿️ Free Onsite parking 🍗BBQ - Outside dining 🏊‍♀️Heated Private Pool 🗑️Washer & Dryer 👫Kids friendly 🎱⛳️🏓Family games: Pool Table, Golf, Ping PongTable

A tranquil backyard features a sparkling pool surrounded by lush greenery and palm trees. Sunlight reflects off the water, creating a serene atmosphere. A covered seating area adds to the comfort, enhancing the outdoor space that overlooks a picturesque view of Lake Gandy.

4.88 out of 5 average rating, 104 reviews

Recharging Lakeview Oasis w/Pool centrally located

Fall in love w/ our peaceful home w/ incredible backyard & pool overlooking Lake Gandy! Experience the tranquility of this safe, residential area. New furnishings for your comfort, cozy living room w/ an 85" Smart TV, comfortable bedrooms, laundry room & fully-equipped kitchen for a nice meal. Have fun at our spacious backyard, great for entertainment, bbq's & fire pit s’mores nights! Enjoy delicious organic fruit in the yard! Only 25min away from amusement parks & MCO! Superb for long stays!

Two wooden cabins are positioned under tall trees, reflecting on the calm water's surface. A small seating area with bright blue chairs and a fire pit is situated on the grassy shore, providing a relaxed outdoor space, while the surrounding nature complements the serene setting.

4.94 out of 5 average rating, 227 reviews

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow cleaning and disinfecting of the house

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.

4.92 out of 5 average rating, 225 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.

4.98 out of 5 average rating, 197 reviews

The exterior of the property features a fenced yard with shaded trees and a front lawn leading to a single-story house. A pool area with protective mesh surrounds the heated pool, illuminated with vibrant LED lights in evening settings. Indoor spaces exhibit an open layout with natural light and comfortable seating.

Home in Minneola

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 - $50 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}

4.99 out of 5 average rating, 100 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

Welcome to Sol Oasis Cove! This amazing pool / spa cottage has one bedroom on the first floor and 2 bedrooms upstairs with a balcony positioned perfect for the sunset over the lake! This property comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater.

4.96 out of 5 average rating, 102 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

This unique place has a style all its own. Dogs Welcome! ( Pet fee applies). Newly renovated featuring white tiles throughout, granite countertops, fully equipped kitchen, smart tv in all bedrooms and living space. Modern stylish garden bath with floating cabinetry. This unit also features work space with desk and chair. One car garage and extra parking space included at no extra charge. At this time we are only accepting one pet per reservation, max 30lbs.

Apartment in Winter Garden

4.89 out of 5 average rating, 169 reviews

Stay A While

Welcome to Your Secluded Getaway Enjoy a quiet retreat minutes from supermarkets and Florida’s top attractions. Top Attractions Island H2O: 23m | Epcot: 27m | SeaWorld: 32m Disney Springs: 34m | Universal: 36m Legoland: 1h | Busch Gardens: 1h 27m Shopping & Dining Winter Garden/Clermont: 14m Outlets: 28m | Florida Mall: 35m | I-Drive: 40m Travel MCO Airport: 40m Oversized Parking: Dedicated space for boats, RVs, and moving trucks. storage only

4.98 out of 5 average rating, 151 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

Experience luxury and excitement in our chic modern suite nestled in the vibrant heart of downtown Clermont. Perfectly poised for Triathletes, this suite is a beacon of comfort and convenience, mere steps away from charming downtown boutiques, delightful restaurants and local breweries. The location is unparalleled with close proximity to the celebrated Clermont/Minneola Trail, esteemed host of prestigious Triathlons and the serene Waterfront Park.

4.91 out of 5 average rating, 149 reviews

A welcoming living area features a dark brown sofa adorned with decorative pillows in warm tones. Greenery decorates the wall behind the sofa, complemented by a modern lamp. A nearby circular table and chair set add to the inviting space, with natural light filtering through a window.

Apartment in Kissimmee

Lush Green Retreat 10 Min to Parks Pets Allowed

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 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Popular amenities for Winter Garden pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.89 out of 5 average rating, 108 reviews

An outdoor area features a pool surrounded by lounge chairs and a sleek design. Soft lighting illuminates the space, creating a cozy ambiance. A sauna is visible, with a comfortable lounge area nearby, and a large screen mounted for entertainment.

Home in Longwood

Recharge @ Timberland Lodge: Pool Hottub Sauna

Home in Buenaventura Lakes

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

4.9 out of 5 average rating, 163 reviews

Villa Resort Club

4.99 out of 5 average rating, 107 reviews

Home in Davenport

Pool & Spa Oasis/Golf Retreat/Near Disney/3BR Home

The interior of Hook's Cabin features a spacious living area with natural light flooding through large windows, complemented by modern furniture. A heated pool and outdoor lounge area are visible through the glass doors, highlighting the community's inviting amenities.

4.88 out of 5 average rating, 154 reviews

Hook's Cabin- Lake & Pool near Disney A-frame

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.

4.96 out of 5 average rating, 24 reviews

Entire clean comfortable house

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.

4.93 out of 5 average rating, 14 reviews

Your Enchanted Home Near Downtown Winter Garden

4.98 out of 5 average rating, 178 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

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.

4.91 out of 5 average rating, 176 reviews

Modern Tropical House Heated Salt Pool

Pet-friendly home rentals with a pool

4.79 out of 5 average rating, 24 reviews

Condo in Horizon West

Modern Escape with Private Patio, Spa Tub & Pool

A private enclosed pool is surrounded by a screened patio, offering scenic views of lush greenery and blue skies. The pool is clear and inviting, with sunlight reflecting off its surface, creating a serene atmosphere for relaxation.

4.82 out of 5 average rating, 22 reviews

Scenic View w Pool/Fenced Yard/Centrally located

4.95 out of 5 average rating, 55 reviews

Apartment in Orlando

Epic stay at Vista Cay!

5 out of 5 average rating, 12 reviews

Home in Kissimmee

Montego Bay Retreat | 15 Min to Disney

4.93 out of 5 average rating, 163 reviews

Home in Kissimmee

Private Pool + Spa Game Room •4m Disney •Pinball

4.82 out of 5 average rating, 11 reviews

Private Pool Home Near Disney | 4BR Sleeps 10

5 out of 5 average rating, 28 reviews

The exterior of the villa features a well-maintained landscape with green grass and palm trees. The home has a light green facade, a two-car garage, and arched windows lending a welcoming appearance under a clear blue sky.

Villa in Clermont

Sunset Paradise Villa in Orlando, Disney area.

4.93 out of 5 average rating, 415 reviews

A private outdoor area is showcased, featuring a sparkling pool accompanied by a hot tub. Lush greenery and colorful plants surround the space, while comfortable seating options, including bright blue chairs, invite relaxation. A pergola provides shade, enhancing the tranquil atmosphere.

Guest suite in Orlando

Downtown Orlando Garden Retreat

Private, pet-friendly home rentals

4.98 out of 5 average rating, 65 reviews

Apartment in Apopka

The little Manatee Home - Lake & Wildlife Retreat

Guest suite in Winter Garden

5 out of 5 average rating, 32 reviews

Winter Garden guest suite

4.91 out of 5 average rating, 94 reviews

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

Lakefront in West Orlando Florida

4.86 out of 5 average rating, 28 reviews

The Cottage Winter Garden Walk to Downtown

4.9 out of 5 average rating, 29 reviews

Downtown Winter Garden Luxury Retreat (NO Parties)

5 out of 5 average rating, 17 reviews

1921 Bungalow in Historic Downtown Winter Garden

4.95 out of 5 average rating, 83 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

Sleeps 6 | Car Rental | Prime DTO Location

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.