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.

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Guest favorite
A light-filled living room is depicted, featuring a comfortable white couch with assorted decorative pillows. A wooden coffee table sits in front of the couch, complemented by a patterned area rug. A large television is mounted on a wooden media console, with soft curtains framing the window.
Guest suite in Winter Garden
4.83 out of 5 average rating, 390 reviews

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

Top guest favorite
A children's bedroom features a vibrant underwater theme, with blue walls and colorful murals depicting marine life. Bedding includes a twin-over-twin boat bunk bed and a separate twin bed. Decorative elements like shells and a net create a playful atmosphere, while curtain-filtered light adds a soft glow.
Home in Davenport
5 out of 5 average rating, 139 reviews

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

Top guest favorite
The exterior of a three-bedroom home displays a welcoming entrance with a paved walkway leading to a covered porch. Lush greenery and flowering plants line the front yard, complemented by a white railing. The structure is topped with a metal roof and features large windows.
Farm stay in Apopka
4.96 out of 5 average rating, 101 reviews

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

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, 219 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
4.85 out of 5 average rating, 171 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 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.

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, 176 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 - $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}

Guest favorite
An open studio layout is showcased, featuring a comfortable queen bed with decorative pillows and a soft throw blanket. A multi-functional sofa and coffee table are positioned in front of a flat-screen TV. A dining table for four is also visible, enhancing the inviting atmosphere.
Home in Minneola
4.95 out of 5 average rating, 173 reviews

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.

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, 127 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.

Guest favorite
A wooden porch showcases two turquoise chairs with patterned cushions, overlooking a serene lake view. Lush greenery and soft, hanging moss surround the quiet neighborhood, while a pathway leads to the waterfront, enhancing the peaceful atmosphere.
Guest suite in Clermont
4.93 out of 5 average rating, 130 reviews

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.

Guest favorite
The exterior of the home is shown, featuring a wraparound porch with accessible steps leading up. The structure is surrounded by greenery, highlighting the peaceful countryside setting. Large windows contribute to a light and inviting atmosphere.
Home in Clermont
4.95 out of 5 average rating, 105 reviews

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!

Guest favorite
A charming guesthouse is nestled among lush tropical vegetation, surrounded by diverse greenery and tall trees. Sunlight filters through the leaves, casting dappled light on the exterior and patio area, creating a serene and inviting atmosphere.
Guesthouse in Gotha
4.93 out of 5 average rating, 285 reviews

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.

Superhost
An inviting A-Frame log home is displayed, featuring natural wood paneling and a spacious sleeping area with a neatly made bed. A cozy living space is visible, showcasing a smart TV and comfortable seating. A serene bathroom is equipped with modern fixtures and light blue walls.
Home in Clermont
4.82 out of 5 average rating, 105 reviews

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

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!