Family-friendly holiday rentals in Headington

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Headington

  • Total holiday rentals

    Explore 460 holiday rentals in Headington

  • Nightly prices starting at

    Headington holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 16,390 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    260 properties have a dedicated workspace

  • Wifi availability

    450 of Headington holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Headington rentals

  • 4.7 Average rating

    Headington stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Headington

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

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Guest favourite
A modern kitchen and dining area are depicted, featuring a well-set dining table for eight. Stylish bar stools are arranged around a central island, complemented by sleek cabinetry and ample natural light from a skylight. Decorative touches include a vase of fresh flowers.
Home in Headington
4.97 out of 5 average rating, 107 reviews

New modern 4 bed, 3.5 bath house, free parking

A modern, spacious 4-bedroom, 3.5-bath house in a quiet residential area of Risinghurst. The home is bright, comfortable, and well equipped, with a fully fitted kitchen, fast Wi-Fi, large TV, washing machine, and free private parking. Ideal for families, professionals, and groups visiting Oxford, with easy access to the city centre, hospitals, and universities. This property is not suitable for babies or young children. There is no cot, high chair, or baby gates, more details in safety section.

Guest favourite
The exterior of a charming stone barn is illuminated at night, highlighting its rustic architecture. Soft lighting from below enhances the textures of the stone walls and draws attention to the barn doors. A sculptural feature is visible in the foreground, adding interest to the serene landscape.
Barn in Great Milton
4.95 out of 5 average rating, 236 reviews

17th Century Barn in quiet country village

A 17th Century Hay Barn 7 miles from Oxford and in the same village as ‘Le Manoir aux Quat’ Saisons’. Enjoy a glass of bubbles on your own private terrace before strolling to dinner at this famous Cotswold stone Manor. Fully wheelchair accessible & with private parking this unique property is the perfect place for a few days away walking in the nearby Chilterns, exploring Oxford’s Colleges & Cafes, visiting Art & Literary Fairs or attending appointments at Oxford’s many leading hospitals.

Top guest favourite
The exterior of the brick cottage is visible, showcasing a traditional design with a sloped roof. Large windows allow natural light to enter, framed by lush greenery and garden boxes. The setting features a well-maintained lawn, enhancing the peaceful surroundings.
Cottage in Headington
4.94 out of 5 average rating, 142 reviews

The Coach house in Oxford

The Coach house, a lovely brick cottage built ~1880, has been renovated to provide an open plan, stylish interior. Upstairs sleeps 5 people with a downstairs bathroom. The historic city of Oxford (easily accessible by bus) provides plenty to do and the Thames and Cotswolds are lovely walking areas nearby. The cottage has it's own patio and garden area with trampoline. There is table football, games and books. Off road parking available. It is situated in the grounds of the owner's home.

Top guest favourite
A charming exterior view of a black cabin surrounded by lush greenery. A blossoming tree provides shade to a small white table and chairs set on a paved area. The sky displays soft clouds and bright blue hues, enhancing the peaceful setting.
Cabin in Waterstock
4.95 out of 5 average rating, 171 reviews

Boutique couples hideaway – "The Den"

1-night stays welcome! Privacy, peace and tranquility along with a generous artisan breakfast hamper await couples at ‘The Den’. Single guests also welcome & furry friends too! Just 6 miles from central Oxford. Completely self-contained, refurbished to the highest of standards. Super-comfy double bed, lounge area with Smart TV inc Netflix, WiFi, kitchenette with Belfast sink, mini fridge, microwave, toaster & kettle plus a beautiful en-suite inc fluffy towels & toiletries. Private patio.

Guest favourite
A well-lit bedroom features a spacious bed adorned with a light blue patterned duvet and decorative pillows. Soft towels are neatly arranged on the bed. A stylish mirror and framed artwork complement the grey walls, with a welcoming entrance visible in the background.
Guest suite in Headington
4.86 out of 5 average rating, 283 reviews

The Annexe! A self contained Studio for 2 People

The ideal, cosy retreat in Headington! Re-decorated in Autumn 2024, the Annexe is a fully furnished and well equipped space, making a great and comfortable base for couples or solo travellers. With nearby great bars, restaurants, cafes, parks and shops, the property is also within walking distance of the John Radcliffe, Nuffield, Manor and Churchill hospitals as well as Oxford Brookes University. There are excellent transport links into Oxford city centre, London and major airports.

Guest favourite
Flat in Northway
4.83 out of 5 average rating, 128 reviews

Oxford - Private Flat + Parking

Spacious Ground Floor 2 Bedroom Flat in Northway. Very close to central shops, restaurants, theatres, Oxtord University campus & Oxford Brookes University Campus, 10 minute drive to the centre of Oxford where you can explore the fascinating history of Oxford, Access to all high end clothing shops, Bodleian library, Museums etc. 5 minute walk to John Radcliffe hospital 15 minute walk to headington shops Bus stops to access the centre of oxford with buses running every 10-15 minutes.

Guest favourite
The historic windmill stands majestically against a backdrop of open skies, featuring a stone façade and a brick band near the top. A wooden door leads to the entrance, flanked by a gravel pathway. Lush greenery and fields are visible in the distance, enhancing the rural setting.
Windmill in Oxfordshire
4.97 out of 5 average rating, 230 reviews

The Windmill Blackthorn Hill, Nr. Bicester Village

Featured in the 'Times Newspaper' Top 10 best Places to Stay with Spectacular Views: "A truly amazing experience." Perfect for a romantic escape for 2 or a memorable getaway with family or friends, sleeping up to 4 adults max (+13), with reduced rates for couples wishing to use a single bedroom. If you’d prefer to use both bedrooms, the second bedroom can be prepared for a small additional one-off fee. Bookings for three or four guests automatically include both bedrooms.

Guest favourite
A living area features a dark blue sofa with a patterned throw pillow. A wooden coffee table sits in front, adorned with decorative items. A television and kitchen appliances are visible, while a sliding partition leads to a sleeping area with a light-colored bed and warm wall colors.
Guest house in Headington
4.89 out of 5 average rating, 114 reviews

Lovely 1-bed Annexe in LyeValley

Escape to the tranquility of Lye Valley in Headington. Our family-friendly accommodation, nestled on a peaceful residential street, provides a serene retreat. Surrounded by nature reserves and playgrounds, it's an ideal spot for families. ➣ Close to Churchill Hospital, Nuffield Hospital & Brookes University, it caters to medical & academic needs. ➣ A short bus ride from the Oxford city center offers easy access to landmarks like the Radcliffe Camera & Oxford Colleges.

Top guest favourite
An aerial view captures the Pool House surrounded by lush greenery. A modern pool and hot tub are positioned alongside comfortable loungers on a spacious patio. The sliding glass doors of the house provide access to an inviting indoor area.
Guest house in Garsington
4.95 out of 5 average rating, 554 reviews

The Pool House

Relax and reset at the Pool House. The Pool House provides a quiet location where you can relax away from the world. Swim in our pool, heated during the warmer months. During the colder months enjoy a cold plunge, beneficial for body and mind. Ease your aches and muscles in the hot tub. Please note: you are using the pool and hot tub at your own risk, there is no life guard! Please watch children and non swimmers in the pool and hot tub at all times.

Superhost
An inviting open-plan living area features a comfortable sofa with accent cushions, while a dining table is set with pastries and fresh fruit. A modern kitchen area showcases sleek cabinetry and a tiled backsplash. Bright natural light fills the space, enhancing the cheerful decor.
Flat in Headington
4.78 out of 5 average rating, 132 reviews

Cozy 1BR in Headington, Oxford w/ off-road Parking

Our cozy one bedroom apartment in Headington, Oxford is the perfect home away from home. With its newly renovated interior, underfloor heating, and private parking, you'll have everything you need for a comfortable and convenient stay. The apartment is fully equipped with a 50 inch TV and a fully equipped kitchen, so you can enjoy all the comforts of home. The bright and fun decor will make you feel right at home as soon as you walk through the door.

Guest favourite
The studio's interior showcases an open layout with wooden flooring and high ceilings featuring exposed beams. A modern kitchenette is visible on the right, complemented by warm yellow curtains. A cozy seating area is positioned in the background, illuminated by natural light through the windows.
Flat in Oxford
4.83 out of 5 average rating, 312 reviews

Modern Stylish Studio flat Sleeps 3

A modern self-contained studio garage conversionwith mezzanine floor done to a high standard. This contemporary living is located close to all Oxford hospitals and the BMW plant as well as the beautiful Shotover County Park. It is also a mile away from major bus terminal serving airports and Central London and walking distance from bus routes to Oxford city. Parking is also available on forecourt.

Top guest favourite
A cozy bedroom features a spacious bed dressed in grey blankets and accent pillows. A large mirror is mounted above the headboard, enhancing the sense of space. A nightstand with a lamp stands beside the bed, while a fan is positioned nearby for comfort.
Flat in Oxford
4.98 out of 5 average rating, 100 reviews

Stylish sleek retreat - 2 floors

*PLEASE NOTE* The only bathroom in the property is a en-suite for the master bedroom. This beautiful apartment is located in the heart of Oxfordshire offers a modern yet homely feel for your next getaway regardless If you're visiting for business, leisure, or an escape, you'll find everything you need at this location.

Popular amenities for Headington family-friendly rentals

When is the best time to visit Headington?

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