
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.

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!

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.

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!

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

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

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.

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.

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

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.

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}

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!

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
House rentals with a pool

Recharge @ Timberland Lodge: Pool Hottub Sauna

Cozy House with Private Pool. Kissimmee/Orlando

The Cypress House

Entire clean comfortable house

5 Bedrooms/ 4.5 Bathrooms/ Solterra (7869 OR)

Exquisite Luxury Home Minutes from All Theme Parks

There is no other place you want to be than here.

Private 4-Bedroom home with pool!
Weekly house rentals

Downtown Bungalow with fire pit and putting green

3.5 Acre Modern Country Farmhouse |23 mi to Disney

City Charmer

Pet friendly house w/washer & dryer & AC & Parking

Quiet Home Near the Springs

3-BR 2-BA house-amazing lake view and boat parking

Cozy cottage in Winter Garden

Winter Garden Butterfly Retreat
Private house rentals

Clermont 2 Bedroom Bungalow

PrivateOakForest RanchFirepit, BBQ&FamilyRetreat

Winter Garden Cottage w\fence

3 BR home 5 min to DT Mount Dora | Gym| EV charger

Lakefront in West Orlando Florida

Downtown Winter Garden Luxury Retreat (NO Parties)

1921 Bungalow in Historic Downtown Winter Garden

Luxury Villages Stay • Golf Cart • Near Brownwood
Destinations to explore
- Miami Vacation rentals
- Orlando Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Miami Beach Vacation rentals
- Panama City Beach Vacation rentals
- Tampa Vacation rentals
- Fort Lauderdale Vacation rentals
- Savannah Vacation rentals
- Hollywood Vacation rentals
- Jacksonville Vacation rentals
- St. Augustine Vacation rentals
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Camping World Stadium
- Magic Kingdom Park
- Epcot
- Universal's Volcano Bay
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- University of Central Florida
- Old Town
- ESPN Wide World of Sports
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- ICON Park
- Aquatica
- ChampionsGate Golf Club
- Tinker Field





