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.

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Superhost

Guesthouse in Bennett End

4.86 out of 5 average rating, 436 reviews

Mary's Cabin

Completely peaceful, with fantastic views-totally isolated with its own private entrance. Set in the Chiltern hills- Mary’s Cabin is 2minutes stroll from the Restaurant of the Year- In an Area of Outstanding Natural Beauty;-walking, road & mountain biking- pub 7minutes up through the woods- 35mins from Heathrow and Oxford -Central London-50mins . Couples, solo adventurers, and small families (with 1small child). Sadly, since the advent of Covid, we no longer provide breakfast for our guests

Superhost

Cottage in Englefield Green

4.88 out of 5 average rating, 176 reviews

Luxury 5* House Near Windsor Castle, Ascot, London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the properties look onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

Guest favourite

Barn in Warfield

4.91 out of 5 average rating, 799 reviews

Delightful small converted barn

Unique newly converted small barn, bright, light and self contained. Sleeps 3 adults or 2 adults and 2 children (or 2 small adults) due to restricted height space in loft. Large gravel drive behind big, wooden gates for safe and easy parking. An assortment of Teas, coffee & biscuits. Breakfast is not provided. Situated down a country lane, within the garden of the house, walking distance to pubs and restaurants. Near Lapland UK, Legoland, Ascot, Windsor, Train stations to London and Reading

Guest favourite

Home in Buckinghamshire

4.91 out of 5 average rating, 159 reviews

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 bathroom 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

Guest favourite

Cottage in Baughurst

4.96 out of 5 average rating, 349 reviews

Luxury rural thatched cottage with cedar hot tub.

Beautiful thatched cottage annexe on edge of farmland, with 3 double bedrooms (one adjoining), 2 ensuite bathrooms, beamed living/dining area, well equipped kitchen. King sized beds. Unrestricted access to beautiful large fenced and hedged garden set in 3 acres. Secluded outside dining area under a gazebo. 4 ring gas bbq and fire pit. Exclusive use of cedar hot tub till 10.30pm for a one off payment of £60. Seven path labyrinth sits in our adjacent paddock. A tranquil setting. Chill out time!

Guest favourite

Home in Oxford

4.97 out of 5 average rating, 135 reviews

Beautiful , Oxford House, parking, EV charger

Our beautiful, very spacious Victorian town house is situated in a lovely quiet road favoured by academics and creatives. We have 4 large double bedrooms, comfortable and spacious living spaces and parking for 2 cars. We include crisp white linens and towels which are high temperature washed and the house is deep cleaned. Vibrant East Oxford has some of the best restaurants and cafes. We are a short walk from Magdalen Bridge, the Botanical Gardens, punting and the historic city centre.

Superhost

Bungalow in Watford

4.73 out of 5 average rating, 438 reviews

Garden bungalow - separate entrance

* Self check in if required * Large open plan living/kitchen/dining area with sliding glass door to decking * Over 400 fantastic reviews - book with confidence * Separate double bedroom * Pull out sofa bed * Fully fitted kitchen * American Fridge Freezer * Fast train service to London (18 mins) - station 4 min walk * Quiet dogs welcome & dog sitting through TheLeadRole. * Dedicated off street parking spot * Fibre-optic Wifi, HD TV * Bath/shower * Washing machine & air-dryer * Quiet location

Superhost

Condo in Bracknell Forest

4.85 out of 5 average rating, 180 reviews

Awesome 3 bed with parking & WIFI, town 5 min walk

Fantastic location for business or holiday. 10 min walk from Bracknell train & bus stations. Very close to Ascot for races, 7 miles to Windsor Castle and 6 to Legoland! Sleeps 6, plus the flat downstairs is available separately which sleeps 2- 3. 100mb WiFi Driveway for up to 2 cars (pls ask if in a van) Parking on the left side of drive takes 2 cars one behind the other. Close to London, M4 and M3 5 mins walk to The Lexicon town centre, for restaurants, bars and shopping.

Guest favourite

Cottage in Englefield Green

5 out of 5 average rating, 327 reviews

2 Bedroom Luxury Cottage (Secure & Quiet)

This charming Cottage is located in the picturesque Village of Englefield Green. Just four miles from Windsor Castle, three miles from Wentworth Golf Course and six miles from Ascot Race Course. Heathrow Airport if just six miles away. 300 metres further down the lane is The Royal Air Force Memorial and below that, on National Trust grounds that skirts the River Thames is the Magna Carta Memorial. The Royal Holloway University is a ten minute stroll across the Village.

Guest favourite

Home in Horton

4.88 out of 5 average rating, 322 reviews

Modern, spacious 2 bedroom and secure parking

Modern and spacious 2 double bedroom bungalow is located 5 mins from Heathrow. Bus service to and from Heathrow T5. Windsor, Legoland with close proximity car. Liquid Leisure is merely 2 minutes drive and British Rail Wraysbury train station is within 5mins car or 20mins walk from the property and it goes to Windsor and Waterloo London. Secure gated parking, close to local travel amenities. Comfortably fits 4 and being a bungalow it is suitable for the elderly too.

Superhost

Apartment in Windsor and Maidenhead

4.77 out of 5 average rating, 164 reviews

Central Windsor Apartment Facing The Castle

A delightful 2 bedroom apartment facing Windsor Castle in the heart of the town center. Ideally placed to take advantage of the excellent range of shops, bars and restaurants that Windsor has to offer. Two train stations provide links to London. Activities include horse racing at both Windsor and Ascot, polo and horse riding in Windsor Great Park, golf at Sunningdale and Wentworth and rowing/boating on the River Thames. Ten minutes from Legoland.

Guest favourite

Condo in Windsor

4.92 out of 5 average rating, 120 reviews

Windsor Central Cozy luxury 2Bed 2Bath + Terrace

Welcome to Central Windsor. Only a 10 min walk to Windsor Castle - The Great Park -Local shops -Restaurants Cafes -Pubs -Arts centre -Royal Windsor theatre local Library -Riverside Boat trips B Excellent transport services to London - Heathrow 20 minutes by Car Super comfy king size bed with en-suite wet room plenty of wardrobe space Bonus second bathroom / shower Fully equipped . Small kitchen . Washing machine . private patio & shared garden