Family-friendly holiday rentals in Orpington

4.92 out of 5 average rating, 374 reviews

Condo in Eltham

Free Parking | Private Flat Near O2 & Greenwich

Private self-contained flat with free parking in peaceful Avery Hill, South East London. Ideal for couples, families, business travellers and O2 visitors. Features a private entrance, king-size bed, single bed, sofa bed, shower room, living area, kitchenette, WiFi and courtyard seating. Close to Greenwich, Blackheath, Eltham Palace and The O2, with excellent links to Central London. ✓ Sleeps 4 ✓ Free parking ✓ Self check-in ✓ Private entrance ✓ Fast WiFi ✓Courtyard ✓ Near 02 Arena & Greenwich

4.83 out of 5 average rating, 153 reviews

The exterior of a brick building is shown, featuring three large windows arranged vertically, adorned with white fairy lights. A grey planter sits below one window, while a patterned stone pathway leads to the entrance.

Home in Crockenhill

Stunning 2 Bedroom house with parking

An Annexe of a larger property this is 2 Bedroom house fully equipped with all facilities. Two bedrooms both with double beds so the property sleeps 4 easily we also have a travel cot Central location near junction 3 of the M25 station is 10 minutes walk. Situated in the charming village of Crockenhill ,in the lovely kent countryside. nr to Brandshatch. Please note we only have a bath and hand held shower unit for washing hair The property has access to a stunning large garden. 1 parking space

4.99 out of 5 average rating, 167 reviews

A private garden area is presented, featuring a mix of stone and gravel pathways, surrounded by low-maintenance shrubs and plants. A comfortable lounge chair is positioned for relaxation, and outdoor lighting enhances the space. The entrance to the property is visible in the background.

Guest suite in Eynsford

Lullingstone Eynsford Annexe & Private Garden

Along the Darent Valley, minutes from M25 between Dartford and Sevenoaks (outside ULEZ 😁), surrounded by farmland and horses, we are a mile from Eynsford Village and with short cut to train station less. The Park and golf course are our back garden and The Roman Villa and Castle/World Gardens our neighbours. Lavender Farm is a short walk too and Brands Hatch 10mins drive. Parking on drive and private access to secure garden. 1 bedroom, bathroom, lounge, smart TV, DVD & fully equipped kitchen

Cottage in Sevenoaks Weald

Two wooden lounge chairs are positioned on a stone patio, offering views of the expansive greenery and rolling hills in the distance. Lavender plants line the edge of the patio, enhancing the serene rural setting.

Quiet luxury rural cottage with fantastic views.

Rare, peaceful and spacious newly built cottage with private garden, comfortably sleeps 6. On Greensand AONB escarpment, with spectacular uninterrupted views over the Kent countryside. Rural retreat 2 miles south of Sevenoaks, half an hour by train to London Bridge. On private road. Own access and parking. New kitchen with light and airy dining and sitting area. WiFi. Very private south facing garden and patio. Fantastic walks to local pubs, national trust, great cycling. Use of tennis court.

4.99 out of 5 average rating, 114 reviews

4.97 out of 5 average rating, 116 reviews

An open-plan living area is highlighted by natural light from a skylight. A modern kitchen features a large marble-topped island with seating. A comfortable sofa adorned with patterned cushions faces a wall-mounted smart TV, providing a cozy space for relaxation and gathering.

Boat in Limehouse

Luxurious houseboat in London

The houseboat is a unique place to stay in London, within easy reach of all of London’s landmarks, including Tower Bridge and Tower of London (5 mins by train). The boat is moored within a marina which means that there is very limited boat movement on the water. The houseboat is custom-designed with every possible comfort, including super fast Wifi, smart TV with content streaming services, and supremely comfortable beds. Radiators throughout the boat make this a comfortable year round option.

4.98 out of 5 average rating, 119 reviews

Home in Edenbridge

Taylour House - Historic, unique, yet modern

Welcome to our historic 'hidden gem' Taylour House built in 1468 for the Lord Mayor of London. Quiet yet town centre location with local amenities on your doorstep. Easy reach of Central London, (Edenbridge Town station 10 mins walk) Gatwick and Heathrow. Sleeps up to 10 guests. Private dining by prior arrangement. Perfect for a holiday, family gatherings, birthday celebrations and hen/stag and bridal parties. Full refurbishment carried out in 2023. Children and dogs very welcome.

Guest suite in Chislehurst

A modern studio is set within a well-maintained garden, featuring a private outdoor deck with wooden railings. The entrance is framed by neatly trimmed shrubs, and large sliding doors provide a glimpse of the interior space, which is bright and welcoming.

Garden gem: your private escape

Step into our cozy Chislehurst haven. Less than 45 mins from central London by public transport, our modern studio offers a private entrance, a comfy superking bed, a fully equipped kitchenette, self-contained toilet and shower room. Take a 5-min stroll to the charming village with shops and eateries. Explore London or venture into the beautiful Kent countryside. Ideal for two adults and can accommodate a child. Enjoy free roadside parking. Welcome to your retreat in the heart of SE London!

4.81 out of 5 average rating, 114 reviews

4.91 out of 5 average rating, 217 reviews

An open-plan living area is presented, featuring a circular dining table with modern chairs, a flat-screen TV on a white unit, and a comfortable sofa complemented by a side table. Natural light floods the space through large windows adorned with vertical blinds.

Apartment in Orpington

Spacious Cosy Modern Apartment in Greater London

*FLEXIBLE EARLY CHECK-IN AND LATE CHECK-OUT at no extra cost* A charming, modern, spacious, cosy 2-bedroom apartment for 4-5 guests, conveniently located in Orpington town centre. Only 7-9 mins walk away from Orpington train station (London fare Zone 6) with REGULAR TRAIN SERVICES INTO LONDON (17mins to London Bridge, 20mins to London Waterloo East, 27mins to Charing Cross). Ideal location for visiting London and travelling by car from EUROPE via DOVER (66 miles / 70 mins drive away).

Cottage in Greater London

A cozy lounge area is featured with a spacious sofa and two modern armchairs arranged around a low wooden coffee table. A window allows natural light to brighten the space, while a decorative rug complements the wooden ceiling beams and gentle colour palette.

Gingerbread House in a quiet woodland setting

Gingerbread House, popular with families, is a self-contained annex set within the owners property, bordered by bluebell woodland and arable fields. The house is ideally situated for day trips into central London by train, sightseeing in Kent/Sussex, or events at Brands Hatch. The village of Pratts Bottom and the local pub is within a 8 minute walk. The nearest train stations are a 10 mins drive and offer fast services to London Charing Cross on the Tunbridge Wells/Hastings line.

4.91 out of 5 average rating, 116 reviews

4.98 out of 5 average rating, 144 reviews

Home in Detling

Luxury 5-BedRm • Hot Tub • Games Room • Sleeps 12

Kent Downs AONB • Newly renovated 5‑bed group house (sleeps 12 + 2 infants) for friends and family get‑togethers, birthdays and wedding weekends. Flexible sleeping arrangements, private year‑round Hot Tub with views, big games room (pool/TT/foosball + 86" TV + sofa‑bed), Kamado Joe BBQ patio, superfast Wi‑Fi (1gb fibre) + Ethernet, luxury hotel‑quality linen & towels, parking for 7 cars + EV charger. Great for midweek offsites. Easy M20/M2/A249 access + Bearsted train station nearby.

Guest suite in Chislehurst

One bedroom fully equipped flatlet

Located in beautiful wooded area on outskirts of London: 20 minutes by train to London Bridge. Chislehurst station 7 minutes walk, or 2 minutes bus ride. Village has "old" and "new" part with boutique restaurants & shops incl. supermarket (10-15 minutes walk ). Near the station are Chislehurst caves, restored historic monument & tourist attraction from war time use as a bomb shelter. Around the flat there are beautiful walks , runs & cycling in Petts Wood. House has quiet garden.

4.92 out of 5 average rating, 114 reviews

4.99 out of 5 average rating, 145 reviews

Cottage in Yalding

Gather&Unwind: Gardens, Woodland & Tennis Cottages

Two charming 3-bedroom cottages with private en-suite bathrooms, set within 2.5 acres of Kentish gardens and woodland. Enjoy a tennis court, children’s play area, walking trails and an in-house ice cream parlour stocked with local Taywell Kentish ice cream. Make your own old-fashioned candyfloss and buttery cinema-style popcorn. Perfect for families, friends and wedding guests. Dog-friendly, with historic Yalding village nearby and London just 45 minutes away by train.

Popular amenities for Orpington family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.9 out of 5 average rating, 248 reviews

The self-contained annex features a charming exterior adorned with lush green foliage, creating an inviting entrance. Large windows allow natural light to fill the living space, while the brick pathway leads up to the door, enhancing the property's connection to its surroundings.

Guesthouse in Sevenoaks

Beautifully developed historic stables, high spec

Shepherd’s hut in Rotherfield

Pigeon Hole, Organic Vineyard stay with Pool.

4.98 out of 5 average rating, 281 reviews

4.94 out of 5 average rating, 566 reviews

The spacious bedroom features a comfortable bed dressed in soft linens, flanked by bedside tables with lamps. Exposed wooden beams create a rustic ambiance, while patterned curtains frame the window. A wooden dresser adds character, and a full-length mirror reflects the room's charm.

Barn in Horley

Cosy, Rustic 17th Century Country Barn.

4.92 out of 5 average rating, 453 reviews

A handcrafted lofted sleeping area is supported by exposed wooden beams, featuring a cozy bed with a patterned duvet cover. Below, a turquoise sofa with colorful accent pillows invites relaxation, alongside a low wooden coffee table. Large windows offer views of the surrounding greenery.

Tiny home in Colgate

Beautiful hand-crafted woodland cabin with hot tub

4.97 out of 5 average rating, 176 reviews

The interior features a vaulted ceiling with exposed wooden beams and intricate stained glass details. Natural light fills the space, highlighting the contrast between the rustic wood and modern design elements. A circular structure is visible, contributing to the open and airy atmosphere.

Barn in Plaxtol

Unique luxury self-contained oast house

5.0 out of 5 average rating, 100 reviews

The indoor swimming pool is surrounded by sleek gray tiles and features illuminated walls that enhance the serene environment. A large screen displays scenic imagery, while the clear water reflects the light from the nearby windows, creating a calming atmosphere.

Apartment in West Sussex

Apartment & Private Surrey Hills Heated Spa & Pool

Shepherd’s hut in Meopham South

Shepherds Hut in Harvel

5.0 out of 5 average rating, 101 reviews

Tiny home in Furners Green

Rooftop space is equipped with a circular hot tub and several wooden chairs with cushions. Soft lighting from string lights creates a relaxed ambiance, while the surrounding trees and open field provide a natural backdrop.

Delightful Double Decker Bus with Hot Tub sleeps 4

4.9 out of 5 average rating, 135 reviews

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 188 reviews

A dining area features a round black table surrounded by yellow chairs, placed against a green wall. Dimmable pendant lights hang above the table, and a decorative stained glass window allows soft light into the space. A wooden media console is situated nearby.

Apartment in Lambeth

Woodland Yard *Entire flat* Vintage Artists House

4.95 out of 5 average rating, 100 reviews

The charming exterior of the cottage features a combination of red brick and stone, with a pitched gray roof. A covered entrance is flanked by small potted plants, and a spacious outdoor area includes a picnic table, surrounded by wooden fencing and lush greenery.

Cottage in Wadhurst

Castle Cottage, Wadhurst

4.88 out of 5 average rating, 556 reviews

A spacious interior of the barn features high wooden beams and large windows, allowing ample light to illuminate the area. A long dining table is placed centrally, surrounded by chairs. A comfortable sofa and various lamps create a cozy seating arrangement, enhancing the overall atmosphere.

Barn in Kent

Beautiful 18th century barn.

4.84 out of 5 average rating, 317 reviews

A bright bedroom is presented with a spacious bed featuring a decorative metal frame. Two decorative vases are displayed on either side of a simple nightstand. Natural light enters through the large window adorned with dark curtains. A modern wardrobe stands in the corner.

Home in Greenwich West

Entire Cosy 4 Bed House in Quiet Neighbourhood

4.85 out of 5 average rating, 249 reviews

Condo in Kent

Spacious & Stylish 2 Storey, 3 Bed Apartment

4.99 out of 5 average rating, 101 reviews

The cottage features a traditional two-story design with a charming thatched roof and black timber framing. Lush greenery surrounds the property, while a well-maintained garden showcases colorful flower beds and an expansive lawn, inviting relaxation and outdoor exploration.

Home in East Sussex

Beautiful Countryside Cottage

Place to stay in Addington

A quaint entrance is framed by a variety of colorful flowers, including pink and purple blooms, cascading from hanging baskets and garden beds. The rustic wooden door is set against a whitewashed wall, complementing the charming brick pathway leading up to it.

Petite Gite in an idyllic cottage garden.

4.97 out of 5 average rating, 271 reviews

4.9 out of 5 average rating, 165 reviews

A charming stone cottage is shown with a sloped roof and light blue window frames. Neatly trimmed hedges and small conifer trees are visible in the garden area, contributing to the inviting outdoor space. A wooden door serves as the main entrance.

Tiny home in Kent

The Old Apple Store

Family-friendly home rentals with a pool

4.77 out of 5 average rating, 194 reviews

A separate entrance to the guest studio is visible, framed by a set of French doors. A couple of white chairs are positioned on a small patio, alongside potted plants and colorful containers. Steps lead up to the entrance, inviting guests into a serene garden setting.

Guest suite in Lambeth

Private garden studio with use of pool

4.99 out of 5 average rating, 200 reviews

A clear blue swimming pool is framed by a spacious patio featuring sun loungers and wooden dining furniture. The dark wooden loft conversion is visible in the background, surrounded by leafy greenery and potted plants, creating a serene outdoor atmosphere.

Barn in Loxwood

Country getaway on rural Surrey/Sussex border.

4.99 out of 5 average rating, 138 reviews

A natural swimming lake is surrounded by lush greenery and wildflowers. The clear water reflects the sky above, while a small wooden platform extends into the lake. The serene setting includes expansive fields in the background, creating a peaceful rural atmosphere.

Barn in Bletchingley

Mattie's Loft

5.0 out of 5 average rating, 232 reviews

A spacious interior features a rustic charm with exposed wooden beams and brickwork. A large bed is centered in the room, complemented by a comfortable sofa and a vintage trunk. A desk and chair provide a workspace, while large windows allow natural light to fill the space.

Barn in Kent

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

4.85 out of 5 average rating, 134 reviews

Tent in Merstham

Bell Tent Glamping Single unit, self contained.

4.78 out of 5 average rating, 125 reviews

Home in Camden Town

2BR Victorian cottage w/ Garden near Camden Mkt

4.8 out of 5 average rating, 170 reviews

A large outdoor swimming pool is visible, surrounded by modern apartment buildings. The pool features a sleek design, with a spacious area for lounging that includes seating arrangements under covered structures. The clear blue water reflects the sky, enhancing the tranquil atmosphere.

Apartment in Nine Elms

Stunning 2 Bed in Battersea w/ Pool, Gym & Rooftop