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

Self-contained luxury annex
The Annex is a completely private part of our house for guests exclusive use, located in the historical Kentish village of Leeds, within walking distance to stunning Leeds Castle. Located 5 minutes from J8 M20. Ideal for Leeds Castle. The Kent show ground. 35 mins drive to Eurotunnel & 50 mins to Dover ferry port. 1 hour to London via train. The Annex has it's own private entrance, rear private patio area, sitting room/ fully equipped kitchenette, downstairs shower room/ large upstairs bedroom.

Little Appleby
Dog friendly Little Appleby is located in Egerton, rural Kent, the Garden of England. We are well placed for the tunnel with Folkestone, Le Shuttle 20 miles away. Egerton, adjacent to Pluckley boasts many lovely country walks with the villages of Goudhurst and Sissinghurst within 20 minutes. Rye, Canterbury & Whitstable are within 40 minutes Ashford Designer outlet is 25 minutes away. The nightly rate is £100. The total cost is £117, inclusive of airbnb fees. I do not charge a cleaning fee.

Step back in history and stay in a 14th c home
A 14th Century self contained wing off the main house set in a peaceful location just outside Faversham, Kent. This charming cottage is ideal for anyone wanting to explore Kent. Or if you just want to relax, bring a book or two and relax in front of the woodburner fire. There are bridleways and public footpaths on the doorstep, which are beautiful anytime of the year, being in the heart of the Garden of England. There are many National Trust/ English Heritage attractions in close proximity.

Petite Gite in an idyllic cottage garden.
Come and make yourself at home in this unique hand crafted miniature gite. Tucked away in the garden of a Tudor cottage, situated on the Addington village green just yards from the Angel Inn. Cottage style Kitchenette with miniature Belfast sink and cupboards. Small double raised bed with storage and dining table underneath. Fully centrally heated for those cosy winter/autumnal days. Rose Cottage, as we call it, has been painstakingly restored to create a delightful, light and cosy space.

The Bohemian Basement
The Bohemian Basement is a unique stylish one bed apartment with its own private garden in the heart of Maidstone. The apartment is 1 of 3 within a newly converted Victorian property just minutes walk from the town centres shops, restaurants and bars. Perfectly equipped with everything you’ll need while visiting Maidstone and with the added bonus of having a wonderful private outdoor garden space, makes this a fantastic Airbnb. There is free on street permit parking which we supply.

Garden of Kent
A well built, well insulated, calm, attractive space just waiting for you. Very close to Sissinghurst Castle, Leeds Castle, Headcorn Aerodrome ( often displays of our famous Spitfire) Romney Hythe and Dimchurch railway, Benenden and Sutton Valance Schools, Biddenden Vineyard, Sissinghurst Gardens, The Big Cat Sanctuary and much more. So much to see and do.Great local pubs and foodie places. We are also very close to the Euro tunnel (20 mins) so makes a great stopover en route to France.

Farmhouse 4 posters cinema music room AGA kitchen
Chilston Home Farm is a period farmhouse in the middle of Kent, the Garden of England. We have lovely walks right from the door, it's perfect for exploring historic Kent and there's easy access to trains to London & Europe. You’ll love the period ambiance: the kitchen Aga, cosy log fires. Two of the bedrooms have king-size four-posters. There's even a bijou cinema! Lots of books & games, a piano, guitar & drums for music lovers, pool table & darts. Ideal for couples or larger families.

Unique Self contained lodge within stable setting
This unique stylish property is very close to junction 5 on the M2 with easy access to London. Plan your visits to Canterbury Cathedral, Leeds Castle, Whitstable, Rochester Castle and many other tourist attractions with ease from this central location. The Property is two miles from the closest shop and the nearest train station is Sittingbourne. The property is set amongst beautiful paddocks with horses in livery in the adjacent stables. There is ample secure parking and easy access.

Adorable 1 bedroom guest barn, Boughton Monchelsea
This barn is situated in the picturesque village of Boughton Monchelsea. It has its own private garden with stunning meadow views. It has lots of local amenities to explore and is only 15 minutes drive from Leeds castle and a 15 minute drive to the train station which will take you directly into London. The exposed oak beamed barn is situated next to a traditional oast house, perfect for romantic getaways and people who want to escape the fast pace of everyday life.

The Oast Cottage: Private Annex with own entrance.
We are pleased to offer our refurbished annex with double bedroom, private bathroom, own front door and a private field for dogs. Oast Cottage is a converted stables attached to the main Oast House. The Oast is set in a conservation area of Boughton Monchelsea which consists of converted farm buildings, listed houses and a 16th Century pub (directly opposite). The area boasts many places to visit (including Leeds Castle), countryside walks, as well as numerous pubs.

Peaceful apt, views, garden, WiFi & sunsets
Relax or work in this stylish apartment with private courtyard garden and vintage summerhouse * First floor apartment with free parking * Country views * Wi-Fi * Self check in * 6ft super king bed * Heating * Smart TV * Plus a summerhouse * Under 1 hour train from London * Local pub/food 10 minute walk * Close to country walks * River Medway 1 mile for boating/walks * Not suitable for pets or children * Please note EV charging is NOT permitted on the property*

Hermitage Cottage cosy 1-4 person accommodation.
Hermitage Cottage offers annexe accommodation. Bathed in sunshine in private garden setting. We are a commuters dream with Barming railway station at the door. London Victoria 57 minutes and Maidstone East just three minutes by rail. Fully fenced with garaging for one vehicle., entry by automatic gates. Finished to a very high standard with under floor heating and feature fire place. Your every comfort is assured. Welcome pack included.
Popular amenities for Maidstone District family-friendly rentals
Family-friendly home rentals with a hot tub

Sea View Holiday Flat + Pool & Spa in Countryside

Evegate Manor Barn

Oak Cottage with private log fired jacuzzi hot tub

The Old Stable

Romantic Hideaway & Hot tub in Kent Countryside.

Beautifully developed historic stables, high spec

Plantagenet: A Historic Country Cottage with Pool

Little Yurt Retreat; Tiny Home, Snug, City Centre!
Family- and pet-friendly home rentals

A Kent Coach House getaway for peace and quiet

Beach Retreat. A relaxing stay with a sea views.

Snap Mill Barn Country Holiday Let

Cottage on the historic Pilgrims Way (Lenham)

Character 18th Century annexe in tranquil village

Guest Suit in Leybourne. Nr West Malling Kent

Pretty cottage in the heart of Tenterden

Wendy’s house, cosy off the grid Woodland cabin
Family-friendly home rentals with a pool

Tranquil Country Retreat with Pool & Hot Tub

Stay and Swim at our home & private indoor pool.

Pine tree woodland retreat

Cosy wood burner country views cold water swimming

Alpaca Lodge

Cottage with tennis court and pool

Cosy shepherd’s hut in beautiful Kent countryside

Kent home with a view
Quick stats about vacation rentals that are family-friendly in Maidstone District
Total rentals
350 properties
Nightly prices starting at
R521 ZAR before taxes and fees
Total number of reviews
11K reviews
Pet-friendly rentals
150 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
170 properties have a dedicated workspace
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