
Family-friendly holiday rentals in Maidstone District
Find and book unique family-friendly homes on Airbnb
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!
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

Wooded Bubble tent
Located on a 120 acre farm. The ultimate star gazing pad. The unusual lodging is fully equipped to help you enjoy a excellent and original night. A cosy bed, a toilet, shower, clean towels and a thousand stars over you. Lay in bed turn off the lamps and start counting. Enjoy a relaxing wood burning hot tub with a glass of prosecco, inhale a breath of fresh air and lay back and enjoy the views of the North downs. Tap onto my profile picture see my other bubbles. Not suitable for under 4 years.

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.

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. .

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

Log cabin lakeside retreat in private grounds

Romantic Hideaway & Hot tub in Kent Countryside.

Plantagenet: A Historic Country Cottage with Pool

Magical Yurt, Outdoor Bath & Cinema - City Centre

The Annexe with hot tub & private courtyard

Hoppers' Hideaways - The Hoppers' Halt - Kent

Kent’s Romantic Shepherd's Hut - The Hide

Pancake Lodge - with hot tub and four poster
Family- and pet-friendly home rentals

Snap Mill Barn Country Holiday Let

Taylour House - Historic, unique, yet modern

The Oast Cottage: Private Annex with own entrance.

Gather&Unwind: Gardens, Woodland & Tennis Cottages

Beautiful barn on the South Downs Way

Little Barn Woodland Escape

Off-Grid Lakeside Cabin

Oak Lodge @ The Oaks Retreat
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.

The Orangery, Organic Vineyard stay with pool.

Alpaca Lodge

Kent home with a view

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 | $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 |
Destinations to explore
- Barn rentals Maidstone District
- Rentals with a firepit Maidstone District
- Cabin rentals Maidstone District
- Pet-friendly rentals Maidstone District
- Fitness-friendly rentals Maidstone District
- Rentals with a fireplace Maidstone District
- Smoking-friendly rentals Maidstone District
- Guest house rentals Maidstone District
- House rentals Maidstone District
- Hotel rooms Maidstone District
- Rentals with a patio Maidstone District
- Rentals with pools Maidstone District
- Waterfront rentals Maidstone District
- Rentals with lake access Maidstone District
- Rentals with outdoor seating Maidstone District
- Farm stay rentals Maidstone District
- Shepherd’s hut rentals Maidstone District
- Rentals with a hot tub Maidstone District
- Rentals with an EV charger Maidstone District
- Apartment rentals Maidstone District
- Serviced apartment rentals Maidstone District
- Rentals with breakfast Maidstone District
- Flat rentals Maidstone District
- Cottage 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





