
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.

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

Grand Bubble
Grand bubble sleeps 4 people who can enjoy the ultimate view of nature. You can fall asleep with the stars and wake up to the rising sun. This bubble has the wow factor and includes your own hot tub, BBQ, a shower, a flushing toilet, outdoor chess set and a golf buggy. The bubble is very secluded set at a bottom of a 12 acre field off a woodland. Out side of the bubble is a very large outdoor gazebo with comfy seating and a large gas bbq so even if it rains you can still bbq comfortably.

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.

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.

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.

Northdown Lodge
We are a unique rural modern lodge with every luxury, nestled in 3 acres. Beautiful views and walking on the Northdown's way. Great local pubs to enjoy. No better place to relax and unwind watching amazing sunsets, and perhaps sampling our local wine grown next door. Or put your feet up by the log burner and watch a film from our vast collection, perhaps with a homemade afternoon tea (available to book in advance). Whatever your preference, you wont be disappointed.

Hermitage Cottage 2 Guests 2 Children.
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.

Luxury Spa Retreat: Sauna & Hot Tub
Escape to our exclusive gated spa retreat, nestled on 5.5 acres of serene countryside in picturesque Fawkham, Kent. This private and tranquil haven offers breathtaking views of rolling hills, perfect for relaxation. Unwind in the luxurious sauna, steam room, or hot tub, soaking in the peace after exploring local attractions. Just minutes from Brands Hatch, our retreat blends seclusion with convenience, your ultimate quiet getaway awaits.

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

Romantic Hideaway & Hot tub in Kent Countryside.

Coldharbour Cottage with a Hot Tub

Kent’s Romantic Shepherd's Hut - The Hide

Pigeon Hole, Organic Vineyard stay with Pool.

Daweswood Guest Suite - luxury retreat & hot tub.

Idyllic rural getaway - Elham Valley, Canterbury

Pancake Lodge - with hot tub and four poster

Unique luxury self-contained oast house
Family- and pet-friendly home rentals

The Seagull’s Rest in The Creative Quarter

Sea-view balconies, sunsets, family & dog friendly

Cabin 5mins to beach in Whitstable

The Oast Cottage: Private Annex with own entrance.

Gather&Unwind: Gardens, Woodland & Tennis Cottages

Delightful pet-friendly oast with private garden

Little Appleby

Blackbird shepherds hut
Family-friendly home rentals with a pool

Stay and Swim at our home & private indoor pool.

The Old Stable

➡️ The Barn House ⬅️ Swimming Pond▫️Jacuzzi▫️Chicks!

Bell Tent Glamping Single unit, self contained.

Alpaca Lodge

Badgers Den - Covehurst Bay Holiday Cottage

The Pool Shed with heated swimming pool (may-sept)

Spectacular BEACH VIEW chalet on the cliff
When is the best time to visit Maidstone District?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $245 SGD | $251 SGD | $246 SGD | $242 SGD | $250 SGD | $252 SGD | $260 SGD | $268 SGD | $245 SGD | $246 SGD | $238 SGD | $256 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 340 holiday rentals in Maidstone District

Nightly prices starting at
Maidstone District holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 11,960 verified reviews to help you choose

Pet-friendly holiday rentals
Find 160 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wifi availability
330 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!
Destinations to explore
- Farm stay rentals Maidstone District
- Guest house rentals Maidstone District
- Barn rentals Maidstone District
- House rentals Maidstone District
- Rentals with breakfast Maidstone District
- Serviced apartment rentals Maidstone District
- Rentals with outdoor seating Maidstone District
- Rentals with pools Maidstone District
- Flat rentals Maidstone District
- Waterfront rentals Maidstone District
- Rentals with a firepit Maidstone District
- Rentals with an EV charger Maidstone District
- Apartment rentals Maidstone District
- Shepherd’s hut rentals Maidstone District
- Rentals with a hot tub Maidstone District
- Rentals with lake access Maidstone District
- Smoking-friendly rentals Maidstone District
- Fitness-friendly rentals Maidstone District
- Pet-friendly rentals Maidstone District
- Rentals with a fireplace Maidstone District
- Hotel rooms Maidstone District
- Rentals with a patio Maidstone District
- Cottage rentals Maidstone District
- Cabin rentals Maidstone District
- Rentals with a washing machine and dryer Maidstone District
- Family-friendly rentals Kent
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- Paddington
- Covent Garden
- St Pancras International
- British Museum
- Hampstead Heath
- Kings Cross
- The O2
- Buckingham Palace
- Marble Arch
- Wembley Stadium
- Tottenham Court Road
- Tower Bridge
- London Bridge
- Big Ben
- Trafalgar Square
- Emirates Stadium
- ExCeL London
- Battersea Power Station (disused)
- Royal Albert Hall
- Russell Square
- Olympia Events
- Borough Market
- Clapham Common
- Brighton Seafront





