House vacation rentals in Oakland

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Quick stats about house rentals in Oakland

  • Nightly prices starting at

    Oakland vacation rentals start at G$10,463 GYD 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 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
4.97 out of 5 average rating, 161 reviews

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!

Top guest favorite
Home in Mount Dora
4.97 out of 5 average rating, 107 reviews

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.

Guest favorite
An open living area features modern furnishings, including a sofa and chairs with decorative pillows. A large television is positioned on a media unit. Natural light filters in through window treatments, illuminating the polished concrete floor. A dining area is visible in the background.
Home in Orlando
4.93 out of 5 average rating, 161 reviews

Modern Universal Orlando

Modern Universal Orlando is a stylish and family-friendly home with 2 Bedrooms and 2 Bathrooms that is located right outside the gates of Universal Studios Florida. With 2 beds and a pull out couch there is plenty of room for a family of 6 to set up home base when visiting the parks. From door to door it is a 1 Mile/15 Minute scenic walk to the gates of Universal Studios. A full kitchen, fenced in backyard, and 2 patios give you all the comfort and functionality of home with central location!

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, 104 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
A Mid-Century cottage is presented with a well-kept exterior, featuring light yellow walls and turquoise shutters. A small seating area with two chairs is positioned on the front porch, surrounded by lush greenery, with a manicured lawn extending towards a tree-lined background.
Home in Mount Dora
4.94 out of 5 average rating, 317 reviews

NEW! Artsy Cottage - Walk to downtown Mount Dora

Welcome to the Artsy Cottage in historic downtown Mount Dora... just a quick stroll to quaint restaurants, shops, pickle ball & parks in the downtown district. This Mid-Century home is tucked in a quiet neighborhood with older historic homes built in the early 1900s, surrounded by towering oak trees and shaded sidewalks. Featuring 3 large bedrooms and 2.5 baths, there is room for 7 guests. You will enjoy cable TV, WIFI, washer/dryer, a fenced yard for your pet and an open deck. $100 pet fee

Top guest favorite
Home in Minneola
4.98 out of 5 average rating, 171 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
The open living area features modern decor with a neutral palette and touches of greenery. A comfortable seating arrangement includes a black sofa and an accent chair. Large glass doors allow natural light to fill the space, connecting the indoors to the outdoor pool area.
Home in Orlando
4.98 out of 5 average rating, 122 reviews

The Perfect Home - Heated Pool - Next to Universal

This luxurious, modern, completely remodeled single-family home with HEATED pool and spacious FULLY FENCED backyard in one of Orlando's best neighborhood! Centrally located from all Orlando has to offer: ☆ 1.7 miles from Universal Studios ☆ 2.6 miles to Restaurant Row ☆ 4.5 miles to Orange County Convention Center ☆ 6.5 miles to Seaworld ☆ 10 miles to Disney World This home offers upscale living space with stunning outdoor area to kick back and enjoy after a long day at the parks.

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
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
4.91 out of 5 average rating, 222 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, 193 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
Home in Apopka
4.99 out of 5 average rating, 142 reviews

5 Springs Close Goats Chicken Free Eggs Memories

COME PLAY AND PET THE GOATS! 5 natural springs 4 to 10 minutes away Fur Babies WELCOME FREE Farm Fresh Eggs Feed the Chickens NO ROOSTERS! Fire pit (we set up the wood daily) Tree swing/bench swing Cornhole Grills Picnic pavilion 5 Acres 2 King Beds 1 Twin pull-out 1 Full size pullout Fully stocked kitchen. Disney 40 min Rock Springs 3 min Kings Landing, Kelly Park, Wekiwa Springs, Barrel Springs, and Wekiva Springs are all less than 5 MILES away. Wekiva Island is a must-visit!

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.

Popular amenities for Oakland house rentals

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  3. Florida
  4. Orange County
  5. Oakland
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