Family-friendly holiday rentals in Penn

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Penn

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A bright kitchen scene is visible through a set of white-framed windows, showcasing a lush garden outside. A stainless steel sink and drying rack are positioned in the foreground, reflecting natural light. The garden features greenery and blooming flowers, creating a calming view.
Guest suite in Amersham
4.96 out of 5 average rating, 378 reviews

Peaceful, self-contained apartment on two levels

Overlooking private garden, situated in historic old town of Amersham, the apartment, once lived in by Roald Dahl, is close to restaurants, pubs, coffee shops plus fashion boutiques. Own entrance, fitted kitchen with electric hob, oven, microwave, fridge, washing machine. Also sitting room with sofa-bed, TV & DVD player, double bedroom with TV, bathroom with bath and separate shower unit. Full central heating, free Wi-Fi. Secluded outside seating area. Unlimited free parking in High Street.

Superhost
The outdoor dining area features a table with four chairs under a green umbrella. Potted plants frame the space, and the background showcases large glass doors leading into the bungalow. Bright greenery and clear skies enhance the comfortable setting.
Bungalow in Amersham
4.86 out of 5 average rating, 238 reviews

Stunning Chiltern Views from Old Amersham Bungalow

NEW BUNGALOW Kyteway is a self-contained detached studio between the historic town of Old Amersham and the rolling Chiltern Hills. Offering fully equipped kitchen, spacious shower room, double bed in sleeping area, dining table, storage, and sofa bed. BEAUTIFUL VIEWS from private dining patio & separate sun terrace. Short walk to historic old town and easy access to new town (inc station to London) on foot, by car, or local bus. Adjacent to countryside footpaths. Unrestricted on-street parking.

Top guest favourite
An open plan living area is showcased with a dark sofa, light wooden coffee table, and a small round dining table. A floral wall hanging is displayed above the sofa, while natural light enters through a skylight, illuminating the neutral-colored walls.
Guest suite in Amersham
4.98 out of 5 average rating, 133 reviews

Bright self-contained annexe with its own garden

This recently renovated, self-contained, quiet and bright annexe has everything you need for a relaxing stay in the Chilterns. It offers own entrance, open plan living area with a kitchen and a small table, bathroom and a bedroom with a king sized bed. Enjoy your morning coffee or a picnic in the sunshine in your own little garden with table and comfortable chairs. Conveniently located, only 8 min walk to Amersham station and 1 min walk to the high street with many cafes, shops and restaurants.

Guest favourite
Barn in Buckinghamshire
4.96 out of 5 average rating, 346 reviews

Beautiful cosy Scandi-barn in Chiltern market town

A beautiful, calm and cosy space designed to feel like a home from home. Lovingly updated and modernised, whilst retaining original character and features to create a unique guest experience. Uber-clean and free from clutter, everything looks & feels fresh for each stay. The kitchen, carpets, paintwork, doors, windows and VELUX roof-lights have been replaced or updated recently. Located with a parking space in a secure, gated courtyard just moments from the town centre of Princes Risborough.

Top guest favourite
An airy living space is highlighted by high ceilings and natural light streaming through large windows. A mix of seating options, including a gray sofa and a white armchair, surrounds a coffee table. A dining area with white chairs complements a gray sideboard.
Cottage in Amersham
4.98 out of 5 average rating, 161 reviews

Delightful, rural, modern cottage, large garden.

Spectacular , quiet, rural cottage. This cottage contains a large maisonette room with a super-king bed and a downstairs room with two double beds, ideal for up to 4 children who can share or two adults who prefer double beds. The bathroom has a bath with a shower in it. There is a fully operating kitchen/dining room. Lots of walks nearby either to the pubs in Little Missenden, Penn woods and Penn Street or further into Old Amersham. Shared use of a large garden and tennis court.

Top guest favourite
A dining area is set outside with a glass-top table surrounded by four wicker chairs. The exterior of the building is textured, featuring a black front door and a window with white trim, complemented by a small shrub nearby.
Guest house in Loudwater
4.93 out of 5 average rating, 134 reviews

Stunning One Bedroom Annex

The annex is very cosy with free parking on front drive. The bedroom has ensuite and there is a separate living room with a very comfy sofa. There is a garden and outside dining table and gazebo area at the bottom ideal for smokers. Our house has the 'Loudwater' sign right outside our house if you don't see the number 9 in the dark. We are also directly opposite Thanestead Court. Our place is just off junction 3 High Wycombe East from M40 so a great location to get to locations.

Top guest favourite
The exterior of the lodge is shown, featuring wooden walls and a slate roof. A private courtyard is visible, bordered by greenery and a stone-paved area. Large windows allow natural light to enter the lodge, creating an inviting atmosphere.
Tiny home in Little Missenden
4.97 out of 5 average rating, 239 reviews

The Stable Lodge

The Lodge is light, airy and modern, whilst providing original character and features. An ideal getaway for couples, those visiting family and friends, or somewhere to base yourself for a weekend of walking in the chilterns; this cosy, self-contained lodge is perfect for those looking to get away from it all. Set on a working stable yard surrounded by private ancient woodland accessible to guests. Private fenced garden, however not secure on one side for a determined dog.

Guest favourite
Cabin in Hertfordshire
4.95 out of 5 average rating, 101 reviews

Hagrid Hut Themed - Hot Tub - Warner Bro Studio

Hagrid & Fang are away and would like you to watch over his home, located next to the Forbidden Forest! This unique Glamping experience is conveniently located only 12 minuets drive from the Warner bros Studio Tour & 40 minuets to central London via Chorleywood Metropolitan line. Hagrid's Hut sleeps five wizards - making it the perfect accommodation choice for families and friends. Soak under the stars in the leaky cauldron wood fired hot tub nestled in nature, MAGIC.

Top guest favourite
A cozy corner of the apartment features a decorative fireplace with an ornate mantle. Handwritten notes are displayed above the mantle, and a wooden desk is positioned nearby. A vintage chair and a chandelier add to the room's charm, with warm light filtering through a window.
Apartment in Hertfordshire
4.98 out of 5 average rating, 172 reviews

Wizards Retreat - 8 Mins to HP Warner Bros Studio!

Welcome to ‘The Wizard’s Retreat’ This Airbnb is perfectly located just an 8-minute drive from Warner Bros. Studios, making it the ideal stay for fans visiting the Harry Potter Tour. There's wizard books to read, games to play & spooky potions to see! Whether it’s a spellbinding weekend with friends, a cosy couple’s getaway, or a family adventure, The Wizard’s Retreat has been designed to capture the wonder and excitement of the wizarding world for all to enjoy!

Guest favourite
A modern living area features a stylish seating arrangement with a plush yellow ottoman and a grey sofa. A marble-topped coffee table sits in front, complemented by a flat-screen TV and a wall-mounted clock. The open kitchen area is visible, outfitted with sleek cabinetry.
Flat in Downley
4.87 out of 5 average rating, 170 reviews

The High Street Gallery,

Brand new and renovated to a high standard, This fully fitted apartment is spacious and stylish,everything you need for a nice relaxing stay will all amenities on your doorstep and a good wifi connection, Perfectly located for Downley Common and access to the Chilterns, Hughenden Manor is within walking distance and the Hellfire Caves at West Wycombe are also close by, There is a bus stop outside the property for easy access to High Wycombe town centre..

Top guest favourite
A cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.
Cottage in Warfield
4.98 out of 5 average rating, 330 reviews

Luxury 2 bedroom cottage

Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

Top guest favourite
The studio features a modern double bed positioned centrally, framed by softly lit sconces on the wall. Natural light enters through a window adorned with light curtains. A small desk and chair are placed beside the bed, complemented by a dark, textured rug on the wooden floor.
Flat in High Wycombe
4.94 out of 5 average rating, 345 reviews

Budget Bliss in High Wycombe

A unit on its own, away from the main residence, this is a modern, comfortable annexe with a high-end finish. Ideal for people working in the area, short stops or longer stays. Even for those looking for long country walks and a home away from home for some peace and quiet downtime. Ensuite with a double bed, kitchenette with 2 burner hob, fridge freezer, microwave and lots of storage with a separate built in wardrobe. Sleeps 2 comfortably.

Popular amenities for Penn family-friendly rentals

Quick stats about holiday rentals that are family-friendly in Penn

  • Total holiday rentals

    Explore 30 holiday rentals in Penn

  • Nightly prices starting at

    Penn holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 560 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Penn holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Penn rentals

  • 4.7 Average rating

    Penn stays receive an average rating of 4.7 out of 5 from guests