
Family-friendly vacation rentals in Oakland
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Oakland
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Designer Guest Suite Near Disney/Universal/DT
This newly renovated, modern, and clean apartment has been freshly designed with wonderful & bright colors and all new furnishings. Everything is thoughtfully selected to create the perfect Airbnb stay. You'll have coffee, decaf, tea, 200mbps Wi-Fi, and high-end mattresses with thick memory foam toppers for the perfect night's sleep. You'll stay in the Orlando area, 20min from Disney/Universal/DT Orlando, and minutes from DT Winter Garden, shopping center, & famous 22mile West Orange Bike trail

All 5 star stay with Waterpark, GameRm, Ariel Buzz
★ WELCOME TO IMAGINATION STATION★ The SHORT bullet point version for busy parents - 5 bedrooms, 4 bathrooms - Ground floor is a Queen bed with a bathroom directly across the hall - Upstairs has 3 bedroom: One is master adult room with ensuite bathroom. The other 3 are kid rooms. StarWars have ensuite bath. Mermaid and Buzz share the hallyway bathroom - Stroller, crib, high chair, pack-n-play free for your use - About 5 houses down from club house (walkable) - Pool has safety fence and door al

Farmhouse near the Springs
Enjoy the ducks, chickens, and goats. Wake to the neighbor's rooster crowing. Have fresh eggs for breakfast when the chickens and ducks cooperate. This three bedroom home with a pool sleeps six. It is - 6 minutes to a grocery store, - 12 minutes to Rock Springs or Wekiva Springs, - 15 minutes to the Lake Apopka Wildlife Drive and - 30 to 45 minutes to the major theme parks, depending on traffic. - a 4 minute bike ride to the 22 mile long West Orange Trail. NO PARTIES TWO VEHICLES MAXIMUM

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

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 and 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.

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}

Cozy Studio Near Disney/Universal/Training center
This cozy stylish studio, detached guest house is perfect for short-term or extended stay in the beautiful city of Minneola. Sleeps 2, can accommodate up to 4. Features a large backyard and a fire pit. Close to Downtown Clermont, National Training Center, and 35 minutes to Disney World and other major attractions. This tranquil space features a queen bed with 3" memory foam mattress topper and a spacious living space that has a Multi-Functional Sofa that converts into a Bed.

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.

Gorgeous views near downtown, modern and comfy.
Enjoy this cute birds nest with breathtaking views. This is a small studio with a kitchen and ensuite bathroom, private driveway, porch and entrance. The kitchen is well equipped to cook a beautiful meal. The bathroom has a walk in shower. Downtown Clermont is at 10 min walking distance across 50 HWY. The neighborhood is quiet and peaceful. FWY, Studio is attached to the main house. Please be considerate and respect quiet hours between 10pm and 8am.

3.5 Acre Modern Country Farmhouse |23 mi to Disney
Enjoy your stay at the perfect modern country hideaway located on over 3.5 acres. Spacious open concept living area spanning over 2000 sq ft. Completely refreshed new floor and furniture. All you will hear will be the cows that come wandering up to the property while you swing on the porch! If you want to experience peace and serenity but also some of that Disney magic this is the place for you because it is also within 30 minutes of Disney!

Paradise nook near Orlando's theme parks
A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

Pumba's Place - FUN, Lake, Pool- NO Cleaning fees!
Pumba’s Place is a renovated A-Frame log cabin in the family-friendly gated community of Vacation Village. Perfect for families and adventurers, it features fast WiFi, smart TVs, a fully stocked kitchen & laundry. Enjoy private Lake Louisa access, a heated Olympic pool, tennis, basketball, biking trails & more. Just 25 mins to Disney and 5 mins to Downtown Clermont & the National Training Center
Popular amenities for Oakland family-friendly rentals
Family-friendly home rentals with a hot tub

Independent Unique Lake guest house/kayaks/jacuzzy

Disney Retreat | Huge Pool with Spa | 2 King beds

No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291

Lakeside Paradise, 15 min Disney + Saltwater Pool

Mills Cottage

The Golden Bear Villa | Private Pool & Theater

Epic Disney Villa • Hidden Arcade & Playroom!

Villa with Guest House & Pool-Patio
Family- and pet-friendly home rentals

8th Green Cottage - A relaxing oasis in the city

OMG! Disney Area, Movie Theater, Game Room & Pool!

The Perfect Home - Heated Pool - Next to Universal

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

Peace and Quiet

*1 min walk to Downtown Mt. Dora! Newly updated!

The Coach House -2 bedroom/3 bath Orlando Getaway!

Chez Bienvenu
Family-friendly home rentals with a pool

Luxurious five-bedroom villa with modern comforts

The Disney House • Immersive Rooms • Gaming Lounge

Six bedroom, 3 bath home with pool and spa *

6 BD/ 4.5 BA Sleeps 16! Windsor Cay (16237 SM)

Swim & Chill Hideaway | Heated Pool + Fire Pit

Luxury home | Lakeside Landing

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney

Family retreat near Disney w/ pool
Quick stats about vacation rentals that are family-friendly in Oakland

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

Verified guest reviews
Over 90 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
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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Give Kids the World Village
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- ChampionsGate Golf Club




