
Family-friendly holiday 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.

The Apple Store
The Apple Store is a beautiful and meticulously clean converted agricultural building that sits in the lovely gardens of a 16th Century house. Perfect for a staycation and set in a peaceful, rural location, the property is approximately 1.5 miles from Marden village and .75 mile from Hush Heath vineyard. Ideal for visits to local National Trust and RHS properties like Sissinghurst Castle, Leeds Castle and Great Dixter. Trains from Marden station to London run all day and take less than an hour.

Self-contained annex, with off-road parking.
Self-contained annex in Sittingbourne, perfect if you are visiting the area for work or leisure. Everything you need for a comfortable stay in your own completely private place, with driveway parking and fast WiFi. The accommodation comprises a bedroom /lounge /working room, kitchen and bathroom. The annex, especially the bedroom, is very quiet and peaceful. Located conveniently for the motorway and also easy access to the town centre, train station, shops, takeaways, restaurants and pubs.

Ayleswade shepherd hut in Kent countyside
set in the small village of biddenden in the heart of the kent countryside belonging to a local farming family of many generations .You can expect beautiful country walks with many footpaths and local villages nearby for cream teas and lovely lunches , the nearby village of Headcorn with its straight connections to London or the coast is good for sightseeing, you wake up to views of our sheep and free range chicken and enjoy a relaxing cup of tea.Theres milk ,tea and coffee and our eggs for you

The Strawberry Barns near North Downs Way Kent.
Strawberry Barns are your home-away-from-home in the Kent countryside. Surrounded by the quiet of peaceful woodland, in Bramley Acres in Kingswood, near Maidstone. Strawberry Barns are the ideal base for couples to explore the Kent Downs Area of Outstanding Natural Beauty (AONB), North Downs Way, delightful villages, pleasant woodland trails, and lovely pub walks in the countryside, all within a short distance of 500 acres of beautiful parkland and formal gardens at the historic Leeds Castle.

Sissinghurst Stables in the Garden of England.
Sit and enjoy the large private garden from the sunny south -facing terrace. This rustic home has an authentic feel, with a quirky calming country design, interspersed with antique furniture and botanical artwork throughout. There is a separate TV room and magical mezzanine play area with baskets of toys for children. There is a private, sunny, nature filled garden. Only one hour from London by train which makes it a perfect location for a city trip too. Insta: Sissinghurst_stables_airbnb

Biggin Farm bungalow
Take a break and unwind in the beautiful kent countryside, but still have great access to road and rail networks. Only half a mile away is the newly opened Wishful Thinker pub and restaurant. 1mile away is the village of Lenham, the picturesque square has 2 public houses, a couple of restaurants and a tea room. Historic and beautiful Leeds castle is only 4 miles away and the city of Canterbury is 23miles. Lenham has rail link to London and Ashford. 4.5 miles to junction M20 junction 8.

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.

Maidstone Bungalow sleeps 5 with parking
This stylish bungalow boasts with unique features and has everything you need for a comfortable stay. Open plan living space is airy and bright and compliments fully equipped modern kitchen. This 2 bed fully refurbished single level home sleeps up to 5 people and it can provide both king size and single beds. The bungalow is located in a prominent position in Allington, Maidstone, and it offers off road parking for multiple cars and a private garden.

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.

The Old Engineer, a rural boutique retreat
Our rural boutique accommodation with private entrance and pretty courtyard garden is surrounded by fields. The space is designed with the guests comfort and luxury in mind. It is the perfect spot for a relaxing and peaceful get away. Super king bed (or twin if requested). Located between Tunbridge Wells and Maidstone, close to the Hop Farm and attractions such as Sissinghurst Gardens, Vineyards and many NT properties.

Home Farm Oast Studio
The Studio is in rural location in the garden of a historic Kentish Oast House with views across paddocks and woodland. It is situated above a barn style garage and is self contained with complete privacy. It has a Large bedroom, ensuite bathroom with shower, a modern fitted kitchen and has an outside wooden deck area with bistro table and chairs for your relaxation. Ideal for couples and business travellers. .
Popular amenities for Maidstone District family-friendly rentals
Family-friendly home rentals with a hot tub

Oak Cottage: Hot Tub, Large Patio & Alpaca Views

The Wren Pod

The Old Stable

Beautifully developed historic stables, high spec

Plantagenet: A Historic Country Cottage with Pool

Hoppers' Hideaways - The Hoppers' Halt - Kent

Kent’s Romantic Shepherd's Hut - The Hide

Shepherds hut
Family- and pet-friendly home rentals

A Kent Coach House getaway for peace and quiet

PJ's @ Willow Cottage

The Granary - Luxury conversion in beautiful Kent

Petite Gite in an idyllic cottage garden.

The Oast Cottage: Private Annex with own entrance.

Cosy 1 bed countryside cottage, tranquil location

Guest Suit in Leybourne. Nr West Malling Kent

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

Tranquil Country Retreat with Pool & Hot Tub

Pine tree woodland retreat

Shingle Bay 11

Little Yurt Retreat; Tiny Home, Snug, City Centre!

Cosy shepherd’s hut in beautiful Kent countryside

Kent home with a view

Shepherds Hut, Organic Vineyard stay with Pool.

Spacious barn with pool ideal for exploring Kent
When is the best time to visit Maidstone District?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $227Â SGD | $228Â SGD | $234Â SGD | $246Â SGD | $254Â SGD | $256Â SGD | $264Â SGD | $272Â SGD | $249Â SGD | $249Â SGD | $242Â SGD | $243Â SGD |
| Avg. temp | 5°C | 5°C | 7°C | 10°C | 13°C | 16°C | 18°C | 18°C | 15°C | 12°C | 8°C | 6°C |
Quick stats about holiday rentals that are family-friendly in Maidstone District

Total holiday rentals
Explore 350 holiday rentals in Maidstone District

Nightly prices starting at
Maidstone District holiday rentals start at $39Â SGD per night before taxes and fees

Verified guest reviews
Over 11,230 verified reviews to help you choose

Pet-friendly holiday rentals
Find 150 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wifi availability
340 of Maidstone District holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Maidstone District rentals

4.8 Average rating
Maidstone District stays are highly rated by guests – averaging 4.8 out of 5!
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- Family-friendly rentals United Kingdom
- Tower Bridge
- British Museum
- Westminster Abbey
- Big Ben
- London Bridge
- Covent Garden
- Buckingham Palace
- Trafalgar Square
- The O2
- Hampstead Heath
- Wembley Stadium
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- Alexandra Palace
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- Queen Elizabeth Olympic Park, London
- Hampton Court Palace
- Chessington World of Adventures Resort
- Twickenham Stadium




