Family-friendly vacation rentals in Oakton

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Oakton

  • Total vacation rentals

    Explore 20 vacation rentals in Oakton

  • Nightly prices starting at

    Oakton vacation rentals start at G$8,365 GYD per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oakton vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oakton rentals

  • 4.9 Average rating

    Oakton stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Oakton

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
A quaint white cottage, characteristic of the 1900s, is framed by a manicured lawn and colorful garden beds. A stone pathway leads to the front door, while a white picket fence surrounds the property, providing a charming ambiance.
Farm stay in Middleburg
4.96 out of 5 average rating, 124 reviews

The Blacksmith Cottage

Just 1 Mile from Historic Middleburg, VA! 🐄✨ Step back in time at our cozy 1900s blacksmith’s cottage—fully renovated with modern comforts but still full of old-world charm! This one-room hideaway is perfect for relaxing, unwinding, and soaking in the countryside. Roam our 66-acre farm and say hello to our mini-Highland cows, rare Kerry Hill sheep, and the cutest mini donkeys you’ll ever meet. 🐑💛🐴 Please note: We’re strictly an Airbnb—no weddings, big parties, or events. No smoking allowed.

Guest favorite
A modern living area features a light gray sofa adorned with various patterned cushions. A coffee table sits atop a geometric-patterned rug, while a small desk and chair are positioned nearby. Natural light enters through nearby windows, complemented by warm, ambient lighting.
Apartment in Falls Church
4.91 out of 5 average rating, 132 reviews

The Happy Heaven

Welcome to ‘’ The Happy Heaven ‘’ Nestled in a serene location , this family-friendly retreat offers comfortable accommodation and the range of amenities designed for relaxation and convenience. With its proximity to nearby attractions and amenities, including restaurant, shop and recreational activities, you’ll have everything you need for a memorable and enjoyable stay . Whether you’re seeking a peaceful retreat or an adventure- filled vacation The Happy Heaven offers the best of both worlds.

Top guest favorite
A modern living area is highlighted by a comfortable sectional sofa adorned with colorful cushions. A round coffee table sits in front, with a decorative item placed on top. Large windows allow natural light to illuminate the space, framed by soft curtains and offering views of greenery outside.
Apartment in Sterling
4.99 out of 5 average rating, 112 reviews

The Potomac Perch-Peaceful Cozy Family Apt

Step into a calming and contemporary haven. This thoughtfully designed one-bedroom apartment features a spacious bedroom with full bathroom , a modern full kitchen perfect for preparing your favorite meals, and comfortable living areas. The bright and airy layout, with its clean lines and tasteful decor, creates an inviting atmosphere for relaxation after a day of exploring. Nestled in a quiet and peaceful neighborhood along Broad Run Drive, you'll be just moments from the scenic Potomac River.

Top guest favorite
The stone cottage is set among lush trees and manicured greenery. A spacious lawn stretches in front, offering ample outdoor space. The house features a covered entrance with a flag, and large windows allow for natural light to fill the interior.
Home in Annandale
4.94 out of 5 average rating, 207 reviews

SUPER HOST! - Cozy Family Cottage

Charming and spacious one level 1940's stone cottage in the heart of Northern Virginia. Cozy and warm and only 20 minutes out of our nation's capital. Large fully fenced yard for kids, dogs, and outside entertaining. Outdoor amenities include a huge patio seating area, a fire-pit, and a gas grill. Inside there is a gourmet kitchen, two fireplaces and a beautifully decorated living area. Master bedroom is set-up like a resort with a very comfortable king size bed and luxury master bathroom.

Guest favorite
A cozy sleeping area is presented with a spacious bed dressed in soft, light-colored bedding. Two bedside lamps provide warm illumination, complementing the neutral tones of the walls. A small side table and a wooden accent table are positioned beside the bed.
Guest suite in Oakton
4.82 out of 5 average rating, 154 reviews

N. Virginia convenience to DC and Old town Vienna

This is a finished lower level of a townhouse in a quiet Oakton, Virginia suburb of Washington DC. The private entrance side is above ground. The large French doors allow lots of light in. We are located half way between Regan National and Dulles airports with public transportation to both. The bus stop is 50 yards from the door and the bus trip is less than 2 miles to the Vienna/George Mason University Orange line metro station. You will have key to the private entrance and laundry room.

Top guest favorite
Home in Takoma Park
4.92 out of 5 average rating, 106 reviews

3BR Luxury Retreat, Pond, Gym, Near DC

Wake up to birdsong beside a waterfall and lotus pond, just 20 minutes from downtown DC in peaceful Takoma Park. Our spacious 3-BR, 2.5-BA luxury retreat combines nature with urban access— a sanctuary for guests seeking both relaxation and adventure. Parking, home gym, steam shower, EV charger, & five decks. Walk to organic market, restaurants, & scenic trails. Recent whole-house renovation. Our reviews say it all!! Superhost service to top it off. Montgomery County Reg # STR24-0017

Guest favorite
The exterior of a charming cottage features a steeply pitched roof with shingle detailing, two dormer windows, and a welcoming front porch. A white picket fence surrounds the well-maintained yard, which includes neatly trimmed shrubs and an American flag displayed near the entrance.
Farm stay in Purcellville
4.98 out of 5 average rating, 171 reviews

Country Cottage on 1700’s Quaker Farm

Sylvanside is a Williamsburg style cottage on 1740 Quaker farm. 3+ Bedrooms, w/en-suite baths, full kitchen, LR, FR, fireplace & sun porch. View the fields & pond, old barns, English garden. Interact with our Clydesdales, & pig, play in the creek & walk the 25 acres. Perfect getaway retreat for family & friends (No parties, events or filming w/o permission and contract) vineyard visits, apple picking, hiking. Base price 2 guests; $50 each add guest to allow flexibly for group sizes.

Top guest favorite
A modern kitchen is highlighted by clean lines and neutral colors. An island with seating is centered, surrounded by a spacious layout. Appliances include a refrigerator and stove, while artwork adorns the walls, contributing to the inviting environment. Ample natural light illuminates the area.
Tiny home in Reston
5 out of 5 average rating, 165 reviews

Pristine 1BR, king bed, hot tub, close to IAD

Luxurious, private and serene. Central location – 1 mile to the Metro, 8 minutes to IAD and Reston Town Center. Dedicated street parking. Close to multiple shops and restaurants. 2 patios and a side yard. Private use of the spacious hot tub with over-sized towels & luxurious robes. Enormous king-size Sleep Number® bed for exceptional comfort. Chef-worthy kitchen and washer/dryer. Free Netflix, YouTubeTV and Prime; your own thermostat and ultra-fast WiFi. No shared spaces. Built new in 2023.

Top guest favorite
The cottage is a charming two-story building, featuring a dark exterior with large windows. A welcoming porch is accented by steps leading to the entrance, and a stone pathway guides through the lush green yard, surrounded by trees.
Cottage in Leesburg
4.92 out of 5 average rating, 398 reviews

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

Guest favorite
A living area is highlighted by a deep green accent wall and a flat-screen television mounted above a decorative rug. A comfortable sofa with throw pillows sits adjacent to a small dining table with a chair. A potted plant adds a touch of greenery to the space.
Townhouse in Fairfax Station
4.9 out of 5 average rating, 107 reviews

Cozy Private Entry 1BR1BA Suite Close to GMU & DC

Welcome to your beautiful one-bedroom suite with a modern and cozy interior. This private space features a walkout basement with its own entrance, ensuring privacy and convenience. The suite includes: Bedroom: Comfortable queen-sized bed, large closet Air mattresses: Additional sleeping space if needed. Kitchenette: Fully equipped with essentials . Dining Area Office Desk: Ideal for remote work or study. Updated Bathroom: Includes modern fixtures and amenities. Washer/Dryer

Guest favorite
Apartment in Great Falls
4.96 out of 5 average rating, 127 reviews

Wooded Retreat in Great Falls

Escape to this wooded retreat in Great Falls, perfect for nature lovers and adventure seekers. This basement apartment boasts a dining area with sunlit windows showcasing vibrant forest views, a spacious living room, and a cozy bedroom. Enjoy easy access to hiking, biking, and outdoor fun in the parks just minutes away. Relax in the great outdoors experience the shops and dining in the nearby village. A perfect blend of nature and adventure awaits at this charming getaway.

Top guest favorite
A living area is presented with a large television on a sleek stand, displaying streaming service options. Two framed pictures adorn the wall above, and natural light enters through two nearby windows, enhancing the neutral tones of the room.
Apartment in Reston
4.97 out of 5 average rating, 266 reviews

Great Location w/ Cozy Atmosphere

Our quaint apt is perfectly located minutes from Dulles Airport, Metro, DC, restaurants, shopping centers & entertainment options. A finely decorated apartment providing all the essentials you'll need for your stay. We hope you like what you see! ... Looking to take a trip to Shenandoah National Park but still close to the city, then we got the spot for you. You don't have to sacrifice one for the other and enjoy both environments.

Popular amenities for Oakton family-friendly rentals

When is the best time to visit Oakton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$47,261 GYDG$49,770 GYDG$45,379 GYDG$55,625 GYDG$51,025 GYDG$57,926 GYDG$60,017 GYDG$54,789 GYDG$54,371 GYDG$58,971 GYDG$54,580 GYDG$53,952 GYD
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