
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.

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.

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.

Oak Lodge @ The Oaks Retreat
This memorable place is anything but ordinary. It is The Oaks Retreat, WINNER of the Paris Design awards 2024 'best hospitality interior', an architecturally inspired bespoke woodland Airbnb located in the seaside town of Whitstable. The Oak Lodge offers 2 king size bedrooms fully customized with high-end finishes which to need to be seen in person to be fully appreciated. Our Wellness area is equipped with a log burning sauna, a cold plunge and outdoor shower.

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.

Oak Cottage: Hot Tub, Large Patio & Alpaca Views
🥂 Oak Cottage: Hot Tub & Private Patio Escape to Oak Cottage in charming Harrietsham, at the foot of the North Downs. Enjoy a wood-fired hot tub on your large private patio and soak up the views. Located on a smallholding with alpacas, pigs, and sheep (Bam!), expect tranquility and wildlife. Includes our signature homemade welcome pack. Ask about our celebration decorations! Book your perfect Kent getaway.
Popular amenities for Maidstone District family-friendly rentals
Family-friendly home rentals with a hot tub

Kentish country side, Hot tub, great outside space

The Wren Pod

Little Willow Barn

The Old Stable

Romantic Hideaway & Hot tub in Kent Countryside.

Plantagenet: A Historic Country Cottage with Pool

Romantic Getaway with Hot Tub for 2

Daweswood - Luxury countryside cottage, lake & tub
Family- and pet-friendly home rentals

Snap Mill Barn Country Holiday Let

Petite Gite in an idyllic cottage garden.

Beautiful barn on the South Downs Way

Little Barn Woodland Escape

Cosy Thatched Cottage in Kent | Hot Tub | Sleeps 6

Cosy 3 bedroom cottage in the heart of Kent

Little Appleby

Pretty cottage in the heart of Tenterden
Family-friendly home rentals with a pool

Stay and Swim at our home & private indoor pool.

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

The Orangery, Organic Vineyard stay with pool.

Alpaca Lodge

Kent home with a view

Badgers Den - Covehurst Bay Holiday Cottage

Cosy spacious barn ideal for exploring Kent

The Pool Shed with heated swimming pool (may-sept)
When is the best time to visit Maidstone District?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $244 SGD | $250 SGD | $245 SGD | $241 SGD | $249 SGD | $252 SGD | $259 SGD | $267 SGD | $244 SGD | $245 SGD | $238 SGD | $255 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
- Rentals with a firepit Maidstone District
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- Paddington
- Covent Garden
- St Pancras International
- British Museum
- Hampstead Heath
- Kings Cross
- The O2
- Buckingham Palace
- Marble Arch
- Wembley Stadium
- Tower Bridge
- Tottenham Court Road
- London Bridge
- Big Ben
- Trafalgar Square
- ExCeL London
- Emirates Stadium
- Battersea Power Station (disused)
- Royal Albert Hall
- Russell Square
- Olympia Events
- Borough Market
- Clapham Common
- Brighton Seafront





