
Holiday rentals in Headington
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Quick stats about holiday rentals in Headington

Total holiday rentals
Explore 1,260 holiday rentals in Headington

Nightly prices starting at
Headington holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 59,040 verified reviews to help you choose

Family-friendly holiday rentals
460 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
610 properties have a dedicated workspace

Wifi availability
1,250 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 holiday rentals in Headington
Guests agree: these stays are highly rated for location, cleanliness and more.

Cosy 2-Bed Flat Central Headington 2x Free Parking
Welcome to Your Home Away from Home in Central Headington situated outside the congestion zones. Stylish, fully furnished 2-bedroom property offers a perfect blend of comfort, convenience, and modern living in one of Oxford’s most desirable neighbourhoods. Ideally suited for professionals, medical staff, students, or visiting guests, the home provides a peaceful retreat with excellent access to Oxford's hospitals, universities, and city centre. Enjoy privacy, comfort, and a prime location.

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.

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.

Spacious & Stylish Oxford Home
Stunning 2 bedroom Victorian home located in the heart of Headington, Oxford. Recently updated whilst retaining its period character features, this beautifully furnished property is the perfect place to stay while visiting Oxford. Just a 5 minute walk from Headington's London Road which is home to an abundance of restaurants and shops, and only a 10 min bus or taxi ride to Oxford's city centre. * Host My House manages this property which is owned by the Warner family *

House in Oxford
Experience Oxford at its finest from this beautifully refurbished holiday home, located in one of the city’s most sought-after neighbourhoods. Perfect for families, couples, academics, or professionals, this elegant property offers the ideal blend of comfort, style, and convenience. Off-street parking is available, and excellent public transport links make it easy to explore Oxford’s colleges, museums, and cafes, or even take a day trip to the Cotswolds or London.

** 2 Ashbrook Windmill - Luxury ground floor 1 bedroom flat ****
Ashbrook Serviced Apartments provide over 20 serviced apartments of all sizes across Oxfordshire. See our web page for further information.Ashbrook Windmill Flat 2 is a brand new, high specification ground floor serviced apartment in the Headington area of Oxford, UK. The apartment, thoughtfully renovated in 2019, comes with secure off street parking, unlimited high speed internet and weekly clean with towel and linen change. Pets incur additional cost.

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.

Mini apartment with parking
Our apartment is ideally located within central Headington and perfect for a single person or couple. Accessed via a separate entrance to the main house, the apartment is completely self contained. The layout includes a bedoroom with standard double bed, large ensuite shower room, and separate kitchen. Guests have access to a shared garden, which includes a patio and BBQ area. The booking includes off street parking for a medium sized car.

Luxe Penthouse on Cuckoo Lane + JR Hospital
Can’t decide between a city break or a country getaway? Stay in this luxury penthouse overlooking Cuckoo Lane and have the best of both worlds - a modern residence close to the action yet decorated like a country pile with antiques and art. This fully furnished apartment has two large bedrooms with an open plan living and dining room which is filled with light from dawn to dusk. Perfect for exploring the City of Dreaming Spires!

Oxford 3-Bed House | Garden | Parking for 2
Spacious 3 bedroom house with garden and parking for 2 cars, located on London Road on the eastern edge of Oxford. Sleeps up to 7 guests (king, 2 doubles, 1 single) with a bright living room, separate dining room, fully equipped kitchen and 1.5 bathrooms. Close to JR Hospital, Churchill Hospital and Oxford Brookes University, with excellent bus links to Oxford city centre and London. Easy access to the A40, M40 and Oxford Ring Road

West Lodge Studio
Newly renovated studio with private entrance adjoining a detached house. The apartment is set within a large, quiet garden in the attractive Old Headington conservation area. Exceptional views of the Oxfordshire countryside with access to our tennis court if requested. Easy access to Oxford by bus/car, JR hospital (5-minute walk), Headington shops and buses to London (10-minute walk). Off-street parking available.

Kazbar Apartment – Luxe Oxford Stay
Kazbar Apartment is a stylish one-bedroom duplex tucked between vibrant Cowley Road and St Clements, just 10 minutes’ walk from Oxford’s historic centre. With an airy open-plan living space, designer kitchen, and romantic mezzanine bedroom, it’s perfect for couples or solo travellers. Surrounded by eclectic cafés, bars, and galleries, this chic hideaway blends boutique comfort with Oxford’s creative spirit.
Popular amenities for Headington holiday rentals
Other great holiday rentals in Headington

Unique 1 Bed Oxford Apartment with parking

3-Bedroom Luxury Villa, Oxford, Free Parking, WiFi

Urban Escape in Oxford City & Close to JR Hospital

3-Bed home with Garden & Parking

Bell House Oxford - The Quill

Stylish 2-Bed Apartment w/ Parking in Oxford

Dove Apartments

Yew Studio - Self contained one bed with parking
When is the best time to visit Headington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $158 SGD | $156 SGD | $164 SGD | $160 SGD | $164 SGD | $174 SGD | $189 SGD | $192 SGD | $180 SGD | $169 SGD | $160 SGD | $167 SGD |
| Avg. temp | 4°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 14°C | 11°C | 7°C | 5°C |
Destinations to explore
- Rentals with a patio Headington
- Rentals with breakfast Headington
- Smoking-friendly rentals Headington
- Bed and breakfasts Headington
- Pet-friendly rentals Headington
- Townhouse rentals Headington
- Rentals with a hot tub Headington
- Serviced apartment rentals Headington
- Guest house rentals Headington
- Apartment rentals Headington
- Flat rentals Headington
- Rentals with a washing machine and dryer Headington
- Rentals with a fireplace Headington
- Family-friendly rentals Headington
- Rentals with an EV charger Headington
- Rentals with a firepit Headington
- House rentals Headington
- Rentals with lake access Headington
- Rentals with outdoor seating Headington
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- Emirates Stadium
- Silverstone Circuit
- Clapham Common
- Cotswolds AONB
- University of Oxford
- Thorpe Park Resort
- Buckingham Palace
- Stonehenge
- Blenheim Palace
- Chessington World of Adventures Resort
- Alexandra Palace
- Big Ben
- Windsor Castle
- LEGOLAND® Windsor Resort
- British Museum
- London Eye
- Primrose Hill
- The National Bowl





