House holiday rentals in Winter Garden

A bright living area features two rattan chairs positioned on a decorative area rug. Framed artwork adorns the wall behind the chairs. A dining area is visible in the background, with a modern table and pendant lighting, creating a welcoming space.

4.97 out of 5 average rating, 133 reviews

Downtown Bungalow with fire pit and putting green

This 1920's home has been fully updated to include new kitchen, bath, fixtures, appliances, and more. The home has 2 bedrooms with one having a king bed and the other a queen bed. Beds feature super comfy Tuft & Needle mattresses ! Kitchen covers all of your basic cooking needs, has stainless appliances, refrigerator with ice maker, and Keurig coffee maker. The dining table comfortably seats 4 and is perfect for a meal or to use as a work space. New full size washer and dryer in carport laundry room. Grab a bottle of wine from Tony's less than 1 block away and relax in the screened-in front porch. Depending on the season grab a Valencia orange off the citrus tree in the back yard. You can use the entire home! There are 2 spacious bedrooms, 1 bath, dining room, kitchen, and a full washer and dryer in the laundry room (located in the carport). Owners live less than a mile away and are available as needed. We can meet you if you need anything! Just a few short steps from the famous Farmer's Market, Crooked Can Brewing, the Plant Street Market, the West Orange Bike Trail, Garden Theater, countless restaurants, and all that Downtown Winter Garden has to offer. This historic home is the perfect escape from the bustle of the tourist district, less than 30 minutes to Disney World, 25 minutes to Universal Studios, 30 minutes to Sea World. You can easily walk the 1 block to Plant St where most of the amenities of Downtown Winter Garden are located. You'll be just 25 minutes from Universal Studios and I-Drive via the Turnpike and 25 minutes from Disney via hwy 429. Also if you are into biking you can rent them at Wheel Works or the West Orange trail head and hit the famous West Orange Trail. There is a 2 car covered carport on site. Across the street from an elementary school so during the school year, there is some traffic in the morning and afternoon. Please be mindful and a good neighbor!

LocationFamilyLayout

4.97 out of 5 average rating, 162 reviews

A single-story home is set within a spacious yard, surrounded by trees and lush greenery. A driveway leads up to the entrance, while Spanish moss dangles from the branches of nearby trees. The sky is partly cloudy, adding to the tranquil atmosphere.

Home in Montverde

The Legacy House - your home away from home.

Just a block away from the South Lake Bike Trail System, 18 minutes from beautiful Lake Minneola, and a mere 20 miles from the Disney Parks, and 5 minutes from the Bella Collina wedding venue, this peaceful neighborhood home will be a perfect spot to rest after a full day of fun. This is an ideal spot if you're coming for cycling events, fishing competitions, a wedding or simply to enjoy the most beautiful part of Florida! We hope you chose to book with us; it would be our pleasure to host you!

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A spacious outdoor area features a large pool with crystal-clear water, accompanied by a hot tub and a soothing water fountain. Surrounding the pool, a stone patio hosts multiple seating areas beneath a pergola, providing a serene setting for relaxation.

4.96 out of 5 average rating, 110 reviews

Unique Spacious Home w/ Pool near Downtown Orlando

Nestled on a quiet street, 15 mins from Downtown Orlando. This home has a massive pool, hot tub, water fountain, real outdoor and indoor fire place, outdoor patio area w/seating. The Kitchen is equipped with everything you need to make delicious meals, and there are two living areas to provide ample space for relaxation. There is also a designated office area to take work calls. ☀ College Park – 10 mins ☀ Downtown Orlando – 15 mins ☀ Universal Studios – 28 mins ☀ Walt Disney World – 34 mins

LocationValueHot tub

4.98 out of 5 average rating, 181 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.

LocationValueComfort

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, 228 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

ValueFamilyHiking

4.89 out of 5 average rating, 106 reviews

Key West Themed Lakefront Oasis with Sailboat

Please read the entire description before booking (including "policies and rules"). This is the lower half of a large lakehouse. Enjoy a resort-like experience with a private pool, heated spa, and stunning sunsets. With a fun Key West theme, it comfortably sleeps your group and features a separate entrance for complete privacy. Enjoy an outdoor kitchen, fire pit, and even a sailboat for a unique stay. Perfect for families seeking a memorable getaway. Kayaks are included for you to explore.

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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.

LocationFamilyBathroom

4.94 out of 5 average rating, 228 reviews

A modern living space showcases a cozy sectional sofa adorned with patterned pillows, alongside a decorative rug. The open floor plan leads to a bright kitchen area with bar seating. Natural light fills the room through large windows, enhancing the warm wood flooring.

Home in Minneola

Modern Villa in Minneola near Disney, Orlando

Newly renovated modern villa 3 bed/2 bath cozy home nestled amongst beautiful oak trees and close to Downtown Clermont, National training center, and 35 minutes to Disney World and other major attractions. Home features soft comfy beds including one king, one queen, and two twin beds all with 3" memory foam mattress toppers. The kitchen is fully stocked with spices, coffee/tea station, blender and slow cooker. Game room located in the garage is equipped with foosball and air hockey.

LocationFamilyCleanliness

4.98 out of 5 average rating, 130 reviews

Adorable Downtown Lakeview Home 1105

Experience unparalleled comfort and charm in our distinctive Lakeview home, ideally located in downtown Clermont's vibrant heart. This bright and captivating property exudes an inviting aura with its scenic lake views and exceptional decor. Start your day with a refreshing cup of coffee on the serene back porch, take a stroll to the nearby park, or enjoy the array of amenities in the vicinity. Families and athletes alike will enjoy the convenient proximity to key attractions.

ValueFamilyAccess

A modern living space is presented, featuring an open layout that includes a kitchen with dark cabinetry and a dining area with a circular table. Stylish bar stools line the kitchen counter, and a television is positioned in the lounge area, which is complemented by a cozy blue sofa.

4.81 out of 5 average rating, 143 reviews

★★House in Little Loma ★★ 4 beds ★ Jacuzzi

Enjoy this charming remodeled home with 3 bedrooms, 2 bathrooms, and a JACUZZI waiting for your and your family. Each room has a TV. The kitchen has all you need to make a home cook dinner after a really fun day!!! A minute walking distance to VANDERGRIFT CENTRAL PARK which features: Baseball Fields (Lighted), Basketball Court, Volleyball, Boardwalk, Concession Stand, Fishing Dock, Football Field, Non-Motorized Boat Launch, Parking, Picnic Tables, Playground, Restrooms

LocationFamilyCleanliness

A living area features a plush sofa and two armchairs arranged around a circular coffee table. Natural light filters through the window, illuminating the space. A vibrant area rug anchors the seating area, while a bouquet of flowers adds a touch of color on the table.

4.99 out of 5 average rating, 159 reviews

Downtown Winter Garden, Florida

Charming two bedroom, one bathroom home just three blocks from downtown Winter Garden Florida. Across the street from the West Orange Bike Trail and walking distance to restaurants, Splash pond, shopping and Farmers Market. The back yard is shaded by a 100 year old live oak tree. There is a “no pet policy” at the house. We do not accept guests under the age of 12. There are NO cameras on or around the property. I respect the privacy of my guests.

LocationFamilyTV

A scenic view overlooking Starke Lake is presented, featuring a spacious deck with railing. A tranquil pool is visible in the foreground, while vibrant clouds reflect the colors of a sunset in the background, enhancing the natural beauty of the surroundings.

4.9 out of 5 average rating, 182 reviews

Lakeview Sunsets with Loft Escape West of Orlando

We are proud to announce No Smoking on premises property. This Duplex A Lake house overlooks Starke Lake in Central Florida. Great fishing, magnificent sunsets and Disney fireworks every night . Close to Disney 19 miles & 12 miles to Universal & 14 miles to Downtown Orlando. Other activities include air boating, Cape Cape Canaveral and centrally located just 1 hour from ocean or gulf. Please NO SMOKING on premises.

ValueFamilyAir conditioning

Popular amenities for Winter Garden house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 201 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

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A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.

4.93 out of 5 average rating, 157 reviews

Spacious Bungalow with Pool and Courtyard

ValueFamilyLayout

4.73 out of 5 average rating, 178 reviews

Home in Pine Hills

Jo's place

LocationFamilyParking

4.99 out of 5 average rating, 178 reviews

Home in Kissimmee

Private Epcot-Themed Near Disney

LocationValueParks

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, 110 reviews

Recharging Lakeview Oasis w/Pool centrally located

FamilyValuePool

4.98 out of 5 average rating, 112 reviews

A well-maintained exterior showcases a single-story house with a blue garage door and driveway, framed by a lush lawn and shaded trees. Inside, a bright living area is highlighted by modern decor and a large smart TV. A private screened pool is visible, surrounded by seating.

Home in Kissimmee

Minutes to Disney | Kings | Heated Pool | Games

LocationFamilyKitchen

4.86 out of 5 average rating, 123 reviews

The image displays the Summerville Resort sign, highlighting its proximity to Disney. A comfortable bedroom is shown, featuring two spacious beds and colorful wall art. An inviting patio area with outdoor seating is visible, alongside a community pool surrounded by lounge chairs and palm trees.

Home in Kissimmee

Comfy Family Villa|5min->Disney!

ValueLocationCheckout

A private heated pool is surrounded by a spacious stone patio, offering views of lush greenery and a serene lake. Tall palm trees provide shade, while nearby seating areas invite relaxation in this tranquil outdoor setting.

4.96 out of 5 average rating, 228 reviews

Cheerful 5-bedroom POOL Home, Next to Universal

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Weekly house rentals

4.97 out of 5 average rating, 118 reviews

A serene bedroom features a spacious bed dressed in crisp white linens, flanked by modern bedside lamps. A vibrant floral accent wall adds a pop of color, while light filters through plantation shutters, creating a calming atmosphere.

Home in College Park

1927 Bungalow · Walk to College Park Shops

ValueFamilyWi-Fi

4.98 out of 5 average rating, 205 reviews

A spacious living area features a large, deep-seated sectional couch adorned with decorative pillows. A wooden tray rests on the couch. A dining table with chairs is positioned near bright windows, enhancing the natural lighting in the room.

Home in Winter Park

Stylish newly updated home in Winter Park

ValueLocationParks

4.97 out of 5 average rating, 115 reviews

Home in Mount Dora

Beautiful Mount Dora Charmer with Lake Ola Views

ValueLocationBathroom

4.93 out of 5 average rating, 72 reviews

Winter Garden Experience! Walkable Downtown I Pets

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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

FamilyLocationHospitality

4.9 out of 5 average rating, 29 reviews

Downtown Winter Garden Luxury Retreat (NO Parties)

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An open living space features a plush gray couch adorned with light-toned throw blankets. A wooden coffee table sits nearby, complemented by decorative items. Large windows allow natural light to enhance the room's bright ambiance.

4.97 out of 5 average rating, 65 reviews

Cozy cottage in Winter Garden

LocationFamilyIndoor spaces

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.

4.92 out of 5 average rating, 96 reviews

Lakefront in West Orlando Florida

LocationFamilyLaundry

Private house rentals

A living room features a white-brick decorative fireplace beneath a wall-mounted television. Soft gray curtains frame the windows, while light-colored flooring offers a warm contrast. A woven basket rests on a low table in front of a spacious seating area.

4.89 out of 5 average rating, 65 reviews

1921 Winter Garden home 22 min from Magic Kingdom

FamilyLocationHospitality

4.86 out of 5 average rating, 14 reviews

Home in Windermere

Beautiful Comfort & Convenience

FamilyLocationPets

5.0 out of 5 average rating, 44 reviews

Home in Apopka

Spacious Lake Home w/HotTub, Firepit, Grill, Games

ValueFamilyLayout

4.93 out of 5 average rating, 28 reviews

A mid-century home is framed by mature oak trees, providing shade to the grassy front yard. Large windows reflect the natural light, highlighting the clean lines of the exterior. The tranquil setting is complemented by the beauty of the surrounding landscape.

Home in Windermere

Water Front Haven

LocationFamilyCleanliness

The exterior of a single-family home is shown, featuring a well-maintained lawn and landscaping. A garage is visible on the left side, and a welcoming porch with seating is seen in front. A tree provides shade in the front yard.

4.99 out of 5 average rating, 96 reviews

Orlando/Downtown/GameRoom/Disney/Tikihut/MiniGolf

LocationValueWalkability

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.

4.97 out of 5 average rating, 58 reviews

Grandma’s Getaway

ValueFamilyAir conditioning

4.84 out of 5 average rating, 74 reviews

The living area features a spacious arrangement of leather seating, complemented by a circular area rug. A television is mounted on the wall, facing the seating. Stairs lead to the upper level, while natural light enters through the front door windows, illuminating the space.

Home in Apopka

Orlando, Peaceful Waterfront property !

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