
House vacation rentals in Oakland
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Top-rated house rentals in Oakland
Guests agree: these houses are highly rated for location, cleanliness, and more.

Gem. Downtown Winter park, walk to Park av/Rollins
This lovely 3 bedrooms, 2 bath house is located in the most desirable area of Winter Park. Only few steps from Park Ave. You can walk to all the restaurants, Wine room, coffee shops, stores, art galleries, Museum, Park, Rollins College, Winter Park Community Center. Its only 25 minutes drive to the airport, 45 minutes to the beach, and close to family-friendly activities, nightlife, public transport. This house is great for families, couples, solo adventurers, business travelers, and big groups.

Stylish Villa Private Pool-SPA Near Parks Disney!
Stylish villa 4 bed/3 bath family home with private facing pool & SPA, living room, family room, kitchen, breakfast bar, dining table, a game room, Wi-Fi, smart TVs, wheelchair accessible, close to the parks, shops, and restaurants, Pool & SPA heater at additional cost, located at Glenbrook community. We have it all and much more to enjoy. The pool & SPA heater fee is $25 (USD) per day. The BBQ grill is an additional $45 (USD) charge for the whole stay, including 1 propane gas and cleaning.

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.

Cozy Getaway | Game Garage + Fenced Backyard +more
Unwind in a comfortable and well-equipped home! Play pool, fusball, darts, and basketball in the game garage. Conveniently located near Orlando/Sanford Airport, Wekiwa Springs, and a variety of attractions. Enjoy the fully equipped kitchen for all your culinary needs, sleep soundly in comfortable beds, and relax on the spacious back deck with a privacy fence. We have an old school Nintendo 64 and retro Galaga game on the wall to play. Perfect for work, family, or vacation getaway!

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 - $40 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}

2-bedroom home with pool near Kings Landings!
Private 2-bedroom home with a queen size bed and a separate room with a twin daybed. There are many exciting things to do in the area! My home is about 30 minutes from theme parks such as Universal, SeaWorld, and Disney parks. Extra activities to do are Southern Hill Farms to pick fresh fruits and sunflowers. Want more fun in the sun? There is Wekiwa National park which is 7 miles away for kayaking and water springs. Additionally, Kings Landings is located 10 minutes away.

★★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

5 Springs Close Goats Chicken Free Eggs Memories
5 natural springs 4 to 10 minutes away Fur Babies WELCOME FREE Farm Fresh Eggs Pet the goats 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 1 Twin pull-out 1 queen inflatable bed The kitchen is fully stocked. 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!

Stylish Lakeview Home for Triathletes/ Family 380
Experience tranquility at this stylish and inviting Lakeview hideaway. Embrace the comfort promised by our tastefully furnished interiors, supplemented by stunning lake vistas- a perfect sanctuary for leisurely vacations or rigorous triathlon trainings. Triathletes will adore the home's strategic location near running paths, open swimming spots and bike-friendly paths. Our fully complete kitchen is at your disposal to nourish your training regime.

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.

Our Poolhome by the Mouse house with Game Room.
Spacious four-bedroom, two-bathroom residence conveniently located near Disney and Universal Studios. Enjoy the expansive screened-in south-facing pool and fenced backyard for ultimate privacy. Entertain in the fantastic game room, perfect for family fun. Rest assured with 24/7 monitoring of security cameras installed outside the property. Additionally, the pool can be heated upon request for an additional fee—reach out for current rates.

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.
Popular amenities for Oakland house rentals
House rentals with a pool

3 Bd/ 2 Ba Sleeps 7! Calabria (9013 sqm)

Luxurious 5BR w/ Pool, Spa, Game Room & BBQ Grill

Gorgeous 5BR @ Encore Next to Disney - 305

8BR Lakefront themed Villa•Pool•GameRoom•GolfCart

Key West Themed Lakefront Oasis with Sailboat

Mi Casita Near Disney/Universal

Luxury 9Bed W Pool, Movie, Gaming, Next to Disney

Pumba's Place - FUN, Lake, Pool- NO Cleaning fees!
Weekly house rentals

Clear Lake Retreat: Private pool, lakefront

Lakeside Landing on Lake Dora w/ Boat Dock

Clermont 2 Bedroom Bungalow

The Storybook Stay

Disney Villa Huge Pool/Spa + Game Room Fun!

Lakefront Paradise Near Attractions

3BR Oasis DT ORL, Full Kitchen & Fenced Yard!

Winter Garden 2 bedrooms/2 bath home (Downtown)
Private house rentals

3BR Family Home near Orlando!

Indian Ridge Home w/ Pool & Game Room near Disney

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

Mother's place

Executive Villa-Gorgeous South-Side Pool Garden

1921 Bungalow in Historic Downtown Winter Garden

NEW Stuning 09 Bedroom/LED At Pool/ Solara Resort

BellaVida Palms Private Screened Pool Home
Quick stats about house rentals in Oakland

Nightly prices starting at
Oakland vacation rentals start at ﺩ.ﺇ551 per night before taxes and fees

Verified guest reviews
Over 30 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oakland rentals

4.9 Average rating
Oakland stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Give Kids the World Village
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Reunion Resort Golf Courses - Palmer & Watson




