
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.

Ancient barn with private heated pool and hot tub
This magnificent country property, complete with an award winning heated pool complex is set high in the chiltern hills, bordering an area of outstanding natural beauty yet located only half a mile from the London Underground Met Line and Waitrose! Explore acres of orchards, formal and walled gardens, a lake, pergolas, and wild meadows, surrounded by ancient woodland and farmland. Escape to heaven in this spa like tranquil retreat. Leave your stress behind and visit this high tech masterpiece.

Chiltern Barn at Wheeler End, Buckinghamshire
Chiltern Barn is a 230 year old converted hay barn in Wheeler End in Buckinghamshire - half way between London and Oxford, close to Marlow and Henley-on-Thames with easy access to the M40. Wheeler End is a small village in The Chilterns built around a large common. There is a friendly local pub, The Chequers and Lane End, less than mile away has local amenities, including a well stocked Londis, a newsagents, excellent farm shop, gastro-pub, Indian and Chinese takeaways, hair dressers etc.

The Ridgeway Lodge close to Ivinghoe Beacon
The Lodge is a separate building from the main house and has a private patio for relaxing in the sunshine or stargazing at night. The double doors from the patio, lead you into the main, open plan kitchen / living room / dining area. There is a sofa bed with large TV with immediate access to Netflix, iPlayer etc, and super fast WiFi. There is a downstairs loo. Upstairs there is a double bedroom with en-suite bathroom and shower. It has all the amenities for a comfortable and relaxing stay.

Southwood Gardens annexe in Cookham
We are right on the edge of the beautiful village of Cookham. The accommodation is annexed to the main house and is accessed through a secured side-gate for total privacy. There is also free private parking on the front drive. The room is ideal for people who need to commute (1 hour by train to London, 25 minutes drive to Heathrow), or families who need to have additional accommodation for their loved ones to stay in the area. We very much look forward to welcoming you to Cookham soon !

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.

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..

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

Gorgeous Cottage in Skirmett with Parking
This gorgeous 3 bedroom cottage, is in the quiet village of Skirmett, situated in the Hambleden Valley, in a particularly pretty area of the Chilterns. Many films and TV series have been filmed in the area, as it is often thought of as quintessentially English. Just a hop and a skip from London and its airports and a short distance from Marlow, Henley or High Wycombe stations... come and step back in time and enjoy a rural setting you won't forget.

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

The White Cottage Romantic Riverside Retreat

Luxury self-contained Oak Loft - balcony Jacuzzi

Lilly Cottage – Jacuzzi, Views & Dog-Friendly Stay

Luxury Lakeside Hut | Hot Tub | Near Harry Potter

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath
Family- and pet-friendly home rentals

The Garden Cabin

Dog Friendly Cottage 15 minutes to Oxford

Luxury Shepherd's Hut with stunning sunset views!

Stunning riverside house in the heart of Chilterns

Elegant Countryside Cottage near Oxford

Charming Cottage, dogs welcome, private garden .

2 bed house, close to Town Centre

The Old Music Studio - retreat with tennis court
Family-friendly home rentals with a pool

Luxury Battersea studio w open fire, close to Park

Luxury retreat with extensive leisure facilities

Stylish Flat with Free Parking, Gym & Pool

Tulana Taggs - floating home on idyllic island

The Coach House

The Pool House, for 2 adults & up to 2 children

Escape to Country Living at its Finest!

The Pool House
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$8,364 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
Destinations to explore
- Durham Vacation rentals
- Paris Vacation rentals
- London Vacation rentals
- Picardie Vacation rentals
- Grand Paris Vacation rentals
- Thames River Vacation rentals
- Amsterdam Vacation rentals
- South West Vacation rentals
- Inner London Vacation rentals
- Rivière Vacation rentals
- Dublin Vacation rentals
- Brussels Vacation rentals
- Paddington
- Big Ben
- British Museum
- Covent Garden
- London Bridge
- Marble Arch
- St Pancras International
- Hampstead Heath
- Buckingham Palace
- Tottenham Court Road
- Kings Cross
- The O2
- Natural History Museum
- Wembley Stadium
- Piccadilly Theatre
- Trafalgar Square
- ExCeL London
- Battersea Power Station (disused)
- Emirates Stadium
- Royal Albert Hall
- Olympia Events
- Russell Square
- Camden Market
- Borough Market




