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House vacation rentals in Oakland

Find and book unique houses on Airbnb

Quick stats about house rentals in Oakland

  • Nightly prices starting at

    Oakland vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 40 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oakland rentals

  • 5 Average rating

    Oakland stays are highly rated by guests—averaging 5 out of 5!

Top-rated house rentals in Oakland

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite
A bright living area features a light gray sofa adorned with yellow and blue cushions, accompanied by a comfortable recliner. A decorative round ottoman sits in the center on a floral area rug. Natural light enters through two large windows, complemented by light-filtering curtains.
Home in Winter Garden
4.97 out of 5 average rating, 131 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!

Top guest favorite
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.
Home in Orlando
4.97 out of 5 average rating, 105 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

Top guest favorite
Home in Minneola
4.98 out of 5 average rating, 174 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.

Top guest favorite
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.
Home in Clermont
4.94 out of 5 average rating, 226 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

Guest favorite
Home in Orlando
4.84 out of 5 average rating, 186 reviews

Huge pool & Lakeview home | 5 Min Universal

Welcome to your ideal vacation retreat! This spacious and cozy lakefront pool house offers everything you need for a memorable family getaway. Perfectly designed for unforgettable trips with 4 BD and 2 BTH, there's plenty of room for everyone to relax. Located just minutes from Universal, Disney & SeaWorld, this house offers the perfect blend of convenience and tranquility. After a day of adventures, return to your serene lakeside retreat and create lasting memories with your loved ones.

Top guest favorite
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
4.92 out of 5 average rating, 224 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 favorite
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
4.98 out of 5 average rating, 195 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 - $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}

Top guest favorite
A living area features a cozy couch with a blue and white design, paired with a wooden coffee table at the center. Bright light filters through the window with white blinds. The kitchen is visible in the background, showcasing wooden cabinets and modern appliances.
Home in Clermont
4.98 out of 5 average rating, 121 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.

Top guest favorite
Home in Clermont
4.86 out of 5 average rating, 132 reviews

Mario-Themed Home! | Disney 30 Min | Pool + Lake

🍄 Mario's Mini Mansion is a boutique Mario-themed getaway for small families (1-3 kids) and local staycations. > Custom Yoshi’s Fort (queen + twin XL bunk + LIFE-SIZE Yoshi!) > King loft bedroom upstairs > 75" Smart TV + Nintendo Switch (Mario Wonder + games) > 4 streaming TVs > Heated neighborhood pool + large screened patio > Efficient kitchen with Breville Oven/Air Fryer > Sleeps 5 Glow-in-the-dark details, Mario games & more! Something magical for the whole family 🎮

Top guest favorite
An open-concept living area features natural light streaming through large windows with scenic views of the lake. Cozy seating arrangements include a comfortable sectional and accent chairs, complemented by a dining space and a well-equipped kitchen with modern appliances.
Home in Tavares
4.97 out of 5 average rating, 153 reviews

Lake Dora Dream-Waterfront/Pool

Luxurious lakefront home on Lake Dora - 8 minutes to downtown Mount Dora and Tavares. Enjoy your vacation in this newly renovated pool home (Pool Not Heated) on Lake Dora and the Harris chain of Lakes. Bring your boat or rent one nearby to explore the area by water and cruise the Dora Canal to Lake Eustis. Included is a guest apartment with private entrance totaling 4 bedrooms and 4 full baths. Just a half mile to the Tavares Pavilion and dining in downtown Tavares.

Top guest favorite
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.
Home in Winter Garden
4.99 out of 5 average rating, 158 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.

Guest favorite
A modern living area features two comfortable sofas, a wooden coffee table, and a vibrant green plant. A sleek television is mounted on the wall, while the open kitchen area showcases contemporary cabinetry and a light backsplash. Natural light flows in through large windows.
Home in Orlando
4.95 out of 5 average rating, 280 reviews

The Lake House - Next to Universal Studios - NEW ♥️

Luxurious, modern and completely remodeled single-family home with lake access in the prestigious Doctor Phillips neighborhood. Centrally located hops away from all Orlando has to offer, 1.1 miles (3 minutes) from Universal Studios Theme Parks, 9.5 miles to Disney World and 5 miles to Seaworld Orlando. No other Airbnb offers this upscale living space with stunning outdoor area to kick back and enjoy after a long day at the parks.

Popular amenities for Oakland house rentals

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