
Family-friendly vacation 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.

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.

Apartment 24 GERRARDS CROSS
Delightful fully self-contained luxury one double bed apartment with own private entrance (your host is an interior designer). 10 minute level walk to Gerrards Cross village with a vast variety of restaurants, supermarkets and shops. Located 25 minutes from London Marylebone by use of Chiltern Railway Services at Gerrards Cross Station (10-15 minute walk from property) and no more than 40 minute drive from London Heathrow. This accommodation will provide a home away from home experience.

A Hidden Gem
A character cottage, tucked away, in the heart of gastronomic Bray - renowned for its Michelin-starred restaurants: The Waterside, The Fat Duck, the Hind's Head and Caldesi, all within easy walking distance of the cottage. Lych Cottage is a two-bed semi-detached property, completed to a high standard. It provides a stylish place to stay for those wishing to enjoy the comforts of home whilst availing themselves of the local amenities. The first night's stay includes a continental breakfast.

Charming 1 bedroom place with parking.
Relax in the beautiful Chilterns in a comfortable self contained suite with En-suite shower, dining area, 40" Smart TV, fridge. Pub 15 minute stroll away. Nearby towns of Chesham & Amersham have transport links into London and offer a host of restaurants and shops. The Chilterns AONB is well renowned among walkers. We are convenient for The Harry Potter studios (20 min drive) The property is self contained and totally separate from the owner's house so you can come and go as you please.

The Stables, Little Marlow
A fabulous, converted barn, located in the very desirable village of Little Marlow, Bucks. The property is set within 3/4 acre for your private use and has it's own private driveway + parking. The interior has underfloor heating, a wood burning stove, panelled walls, en-suite, and a family bathroom. Little Marlow has been in numerous Midsomer Murder TV series. The village has two pubs, a cricket ground and a church. The property is a 10 min walk to the river Thames. AONB & cons. area

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.

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.

Stunning One Bedroom Annex
The annex is very cosy. The bedroom has ensuite and there is a separate living room with a very comfy sofa. There is a garden and outside dining table. 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 all places in Buckinghamshire as well as to London. The location is very peaceful.

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!

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

Chiltern Hills Escape | Walks & Parking
Set in a peaceful rural location near Saunderton Station, this family-friendly home offers scenic countryside walks and nearby golf courses. Ideally placed for exploring Coombe Hill, Chequers, Waddesdon Manor, the Hellfire Caves and the Roald Dahl Museum, all just a short drive away. The house features a fully equipped kitchen, 65-inch TV, utility room and downstairs bathroom, providing comfort, space and everything needed for a relaxing stay.

Old Butchers Wine Cellar 15th Century Apartment
Our restored 15th century apartment is in a unique position on Cookham High Street, located within 500 meters to 7 different restaurants and pubs and four Michelin Star restaurants within 3 miles. Situated above our beautiful wine shop with a pop up wine bar on Thursday, Friday and Saturday nights. We have very comfortable beds, 100% cotton sheets and towels. The perfect choice for couples, business travellers and families.
Popular amenities for Penn family-friendly rentals
Family-friendly home rentals with a hot tub

The Pool House

The Woodland Cabin with Private Hot Tub Spa

Tinkerbell Retreat

Luxury self-contained Annexe with balcony Jacuzzi

Luxury Lakeside Hut | Hot Tub | Near Harry Potter

Lilly Cottage – Jacuzzi, Views & Dog-Friendly Stay

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

The Mirror Houses - Cubley
Family- and pet-friendly home rentals

Dog Friendly Cottage 15 minutes to Oxford

Stunning riverside house in the heart of Chilterns

Luxury 1 bedroom apartment in St. Albans

The Brickmaker’s Loft

Inclusive, childsafe, garden, near pubs/river/golf

Charming Cottage, dogs welcome, private garden .

Magical Marlow town centre

18th century cottage
Family-friendly home rentals with a pool

The Mill House

Stunning Oak Glass House London Train Hot Tub

Luxury retreat with extensive leisure facilities

Spacious Sunny Apartment

Tulana Taggs - floating home on idyllic island

Wellness Escape by River: Sauna, Pool, Hot Tub

The Coach House

Escape to Country Living at its Finest!
Quick stats about vacation rentals that are family-friendly in Penn

Total vacation rentals
Explore 20 vacation rentals in Penn

Nightly prices starting at
Penn vacation rentals start at G$8,325 GYD per night before taxes and fees

Verified guest reviews
Over 540 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Penn vacation rentals include wi-fi 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
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- Battersea Power Station (disused)
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