
Holiday rentals with a pool in Maidstone District
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Maidstone District
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Blackthorn is a luxurious, rural retreat for two.
Blackthorn is a luxurious retreat for two. Attached to the owner's home, and situated on the edge of Icklesham village, the property lies halfway between the ancient towns of Rye and Hastings. There is a distant view of the sea, and the garden is surrounded by beautiful AONB countryside. The cottage has a private, south facing verandah, and guests are welcome to use the heated, indoor swimming pool and outdoor hot tub throughout their stay but exclusively between the hours of 8.00am and 8.00pm.

Cosy spacious barn ideal for exploring Kent
Nunfield Barn is a beautifully converted barn and one portion of the house is internally separated for our Airbnb guests, with its own entrance, downstairs toilet, kitchen/dining area and living room with doors leading to a private patio. Upstairs there are two double bedrooms and a bathroom with bath and shower. There is an above ground pool for use in summer, a front garden shared with us when we are here. There are fields &orchards across the road and we are 15 minute drive to Leeds Castle

The Cosy Cottage, with heated swimming pool !
Take it easy at this unique getaway, sleeps 4 woodland walks, local pub/restaurant ,Micro brewery and much more to make your time away a memorable one. Relax in the countryside or take a short drive to the local town/Beach. Spend some private time relaxing in our heated swimming pool, and then retire to your own comfort of the "Cosy Cottage" for that long earned rest. Herne Bay,Whitstable towns and the city of Canterbury just 15 mins by car. Local buses run frequently in both directions Enjoy.

Kent home with a view
Annex at the bottom of our garden with its own patio area with views of the pool and garden. Nice quiet area with fields and woodland walks nearby Keys left in door - guests can let themselves in, we are generally around if you have questions There is BBQ area and a heated pool (shared with hosts) for stays of 2 days or more. Please note pool heating is not turned on until about mid-end of May and turned off in September. 5 min to Herne Bay. 15 min to Whitstable 20 min to Canterbury

Little Yurt Retreat; Tiny Home, Snug, City Centre!
The Little Yurt Retreat is the ultimate getaway for couples and families! Enjoy a luxurious Mongolian yurt with a log burner, a cozy Tiny Home with a kitchen, SECRET CINEMA SNUG, shower and... OUTDOOR BATH; live the dream! Perfectly located in central Canterbury—just a 15-min stroll to the city center, a 10-min drive to the beach, or a short walk into the countryside. Fantastic in all seasons, especially winter! Relax, explore & enjoy a romantic escape with modern comforts while glamping.

Plantagenet: A Historic Country Cottage with Pool
A delightful and unique country cottage with historical links to the Plantagenet Kings of England! It's tucked away, surrounded by mature gardens with views over the Eastwell Manor country estate. Plantagenet Cottage is full of character and charm, it's spacious, very private and relaxing . Our heated pool is great in Summer [closed in Winter]. Enjoy the beautiful Kent countryside, great pubs, a nearby Spa, beaches, Canterbury and lots more - or simply just chill out at the cottage !

Peaceful Country Retreat • Pool House & Hot Tub
Escape to our stylish, thoughtfully designed, detached pool house, a peaceful retreat in the heart of the Kent countryside. Surrounded by open farmland and sweeping rural views, this hidden gem offers comfort, seclusion, and charm in an Area of Outstanding Natural Beauty. Spend summer days by the seasonal outdoor pool, unwind year-round in the Hotspring hot tub, or gather by the fire pit under starry skies. Just 5 miles from historic Faversham, it’s a perfect hideaway for couples.

Pine tree woodland retreat
This architect designed self contained studio retreat is surrounded by pine trees and positioned in a secluded side annex to our main family house. The area is surrounded by walking paths and quiet country lanes. It is a newly renovated open-plan space with en-suite shower room and private balcony, tree-top views and direct access to a yoga deck. By arrangement guests may have exclusive use of the heated pool and infra-red sauna which is situated at the rear of the main house.

Shingle Bay 11
PARK FACILITIES REOPEN 20/03/2026 PET FRIENDLY Shingle bay 11 Romney Sands. 3 bed (sleeps 5). 38 x 12FT holiday home. Family friendly site, located opposite Greatstone Beach. A home from home unit with own parking space in a quiet area of the park. Beds freshly made for your arrival. A short stroll to amenities. Everything you need is hopefully thought of. We are a pet friendly home..with a gated deck to keep our furry friends safe.

The Granary, Organic Vineyard stay with Pool.
Coes Farm offers 50 acres of absolute tranquillity in amongst nature, with a bit of luxury thrown in too! We have formal gardens and ornamental ponds, a large lake, plenty of woodland, open fields, an indoor saltwater swimming pool with hot tub, a tennis court and a games room which is resident in our Micro-Winery! We planted our 5 acre vineyard in Spring 2021 and extended the existing Orchard with cider varieties in 2023.

Sea View Holiday Flat + Pool & Spa in Countryside
Luxury studio flat with a spectacular view of the sea and countryside. New: Large private balcony to sunbathe and dine outside. Heated indoor swimming pool, steam room, gym, and outdoor hot tub. King size bed with en-suite, suitable for 2 people. Free high speed wifi throughout. Large smart TV with 200 satellite channels and free Netflix. Located in Hastings Country Park Nature Reserve, short walk to beach.

Railwayman's Hut with Swimming Pond
Enjoy the lovely setting of this romantic spot in nature with use of a natural swimming pond (80m x 20m) . Tucked away in a peaceful location in Kent’s Area of Outstanding Natural Beauty, this enchanting railway man’s hut offers a rural escape from everyday life.
Popular amenities for Maidstone District rentals with a pool
House rentals with a pool

Luxury Whitstable Caravan

Modern Peaceful Static Caravan Seasalter Whistable

Spring Farm Sussex

Sea 'n' Stars with Views, Decking, Wifi & Netflix

The Manor Coach House

Premium Lodge in Camber sands

GWP - Rectory North

Trinity House Cottage
Apartment rentals with a pool

Lovely Flat Zone 2 close to DLR

Magnificent central 2BDR flat,comm gdn

Private apartment - over garden quiet central

Penthouse-Sea View-Balcony-Free Spa-Sauna-Pool-Gym

Seaview Park Luxury Holiday Home, Whitstable.

Luxury Battersea studio w open fire, close to Park

1 Bedroom Apartment In The Heart Of Battersea Park

Lovely 2 bedroom apartment in Canary Wharf
Other holiday rentals with a pool

Beach Holiday Static Caravan

Lovely 3 Bed Caravan, Sleeps 6

Beautiful static Caravan in Whitstable

Camber Sands - Atlanta Sunset

Haven Holiday Park, Kent Coast

Cloth Worker's Barn

Luxury 3 Bedroom Lodge with Spectacular views

Woodland lodge in tranquil Kent countryside
Quick stats about holiday rentals with a pool in Maidstone District

Total holiday rentals
Explore 40 holiday rentals in Maidstone District

Nightly prices starting at
Maidstone District holiday rentals start at £44 per night before taxes and fees

Verified guest reviews
Over 1,490 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 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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- Tower Bridge
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