Family-friendly vacation rentals in Penn

Find and book unique family-friendly homes on Airbnb

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

  • Total vacation rentals

    Explore 30 vacation rentals in Penn

  • Nightly prices starting at

    Penn vacation rentals start at G$8,370 GYD per night before taxes and fees

  • Verified guest reviews

    Over 600 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

    30 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

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
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

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.

Indoor spacesKitchenQuiet

4.86 out of 5 average rating, 259 reviews
Top guest favorite
Cabin in Bourne End

Cosy Cabin

Cosy Garden Studio – Private Entrance & Ensuite. This Cosy garden studio is located at the back of our home, with its own private entrance through the rear gate. It’s a great base for anyone working locally or needing a peaceful overnight stop. Inside, the studio has a double bed, a microwave, kettle and toaster, along with a small sink in the bathroom for basic self-catering & TV We live in the main house, so we’re nearby if you need anything, but you’ll have full privacy during your stay

KitchenFamilyTV

4.97 out of 5 average rating, 101 reviews
Top guest favorite
The charming Victorian Lodge features a classic brick exterior with white trim, framed by lush greenery. Two inviting front windows and a central doorway are surrounded by decorative flower pots. A gravel pathway leads to the entrance, highlighted by an expansive tree nearby.
Cottage in Old Windsor

Gorgeous CountryCottage overlooking Windsor Castle

The Victorian Lodge (1876) is a charming & quintessentially English country cottage on a private estate once owned by King Henry 8th. It sits right beside Windsor Great Park, at the entrance of a long driveway to Little Dower House, where the owners of the Lodge live. The private gardens and stunning view at the Victorian Lodge provide the perfect setting for a small intimate wedding. Whilst the romantic gardens within the Little Dower House estate provide an ideal venue for larger weddings.

Indoor spacesFamilyCheck-in

4.99 out of 5 average rating, 110 reviews
Top guest favorite
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.
Guesthouse in Loudwater

Stunning One Bedroom Annex

The annex is very cosy with free parking on front drive for one guest car. The bedroom has ensuite and there is a separate living room with a very comfy sofa. There is a garden and outside dining table & gazebo area at the bottom ideal for smokers. Our house has the 'Loudwater' sign 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.

KitchenIndoor spacesCleanliness

4.94 out of 5 average rating, 190 reviews
Guest favorite
A charming exterior view of the one-bedroom annexe is presented, featuring a welcoming entrance with a wooden door surrounded by lush greenery and flower pots. A gravel pathway leads to the entrance, framed by large windows that allow natural light into the space.
Home in Flackwell Heath

1 bed apartment. Village location. Heathrow 25mins

This one bedroom apartment is annexed within our family home but benefits from its own entrance and facilities. Quiet village location but easy access to transport links (Heathrow is 20 mins drive, London 35 mins on the train). We are on the edge of the Chilterns, an UNESCO recognised Area of Outstanding Natural Beauty. We are taking bookings using the Covid19 guidelines and legislation set out on the UK government website. If the road map changes then availability may also need to change.

KitchenFamilyRiver

4.9 out of 5 average rating, 135 reviews
Superhost
The farmhouse is set against a backdrop of lush green hills and trees, showcasing a distinct red-brick exterior. Rolling fields are visible in the foreground, complemented by a clear blue sky and scattered clouds, creating a serene countryside scene.
Home in Beaconsfield

Hillmotts Farm with secluded Hot Tub

Hillmotts is a charming, spacious and newly refurbished farmhouse which offers the perfect setting for a countryside getaway. Nestled within a 2,400 acre country estate and surrounded by beautiful woodland, this property boasts all the benefits of the countryside whilst being a prime location approx 40 minutes drive from central London with easy access from the M40. Guests can enjoy use of their very own private outdoor hot tub whilst taking in the fresh country air. Free onsite parking.

Indoor spacesFamilyComfort

4.82 out of 5 average rating, 129 reviews
Guest favorite
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

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.

KitchenIndoor spacesLocation

4.97 out of 5 average rating, 177 reviews
Top guest favorite
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.
Place to stay in Holmer Green

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.

FamilyIndoor spacesAmenities

4.98 out of 5 average rating, 290 reviews
Guest favorite
Cabin in Chorleywood

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.

KitchenIndoor spacesHeating

4.96 out of 5 average rating, 131 reviews
Top guest favorite
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.
Condo in Kings Langley

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!

Indoor spacesKitchenParking

4.97 out of 5 average rating, 224 reviews
Guest favorite
Home in Beaconsfield

18th century cottage

Self contained character annex in the beautiful Buckinghamshire countryside. Low ceilings and a narrow steep staircase with handrail and stairgates top and bottom. Parking spaces at the front and use of garden to the rear. Fantastic location on the edge of the Chilterns; good road and rail links to London, Oxford and Wembley. Close to the Thames, Windsor, Marlow, Cliveden, Hedsor House, Harry Potter Studios and Legoland. Plus there’s a pub next door!

FamilyKitchenCheck-in

4.91 out of 5 average rating, 248 reviews
Top guest favorite
A spacious living area is highlighted by exposed wooden beams and a large window allowing natural light. Two soft white sofas are arranged around a wooden coffee table, with a flat-screen TV positioned on a black stand. A charming brick fireplace adds character to the room.
Apartment in Cookham

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.

FamilyKitchenCleanliness

4.94 out of 5 average rating, 715 reviews

Popular amenities for Penn family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A charming black-clad cottage is softly illuminated by string lights, set against a dusk sky. A picnic table with floral centerpieces occupies the outdoor space, surrounded by a wooden fence. Warm light glows from the cottage windows, creating an inviting atmosphere.
Place to stay in Chorleywood

Hilly Hideaway. Luxury Glamping Retreat + Hot Tub

KitchenIndoor spacesHospitality

4.93 out of 5 average rating, 253 reviews
Guest favorite
The spacious living area features high wooden beams and large windows that allow ample natural light. A fireplace is centrally located, framed by a mix of comfortable seating and a glass coffee table. A staircase leads to the upper level, enhancing the open design.
Barn in Buckinghamshire

Dorney/Windsor Family Getaway with Hot Tub

FamilyIndoor spacesHeating

4.92 out of 5 average rating, 116 reviews
Guest favorite
An indoor pool features a striking wooden ceiling with exposed beams. The tiled area includes a hot tub and a spacious swimming pool, both surrounded by large windows that allow natural light to fill the space. Scenic wall murals enhance the relaxation atmosphere.
Condo in High Wycombe

Country retreat with extensive leisure facilities

FamilyIndoor spacesHospitality

4.89 out of 5 average rating, 116 reviews
Top guest favorite
A serene scene showcases a cottage surrounded by lush greenery and a private lake. Two swans glide across the calm water, while the cottage, with its wooden facade and sloped roof, is nestled among the trees, offering a peaceful retreat in nature.
Cottage in Sarratt

Crestyl Cottage riverside barn for 2 with hot tub

FamilyIndoor spacesHot tub

5.0 out of 5 average rating, 281 reviews
Top guest favorite
Home in Owlswick

Chilterns Country Barn-beautiful views and hot tub

FamilyKitchenNearby

4.93 out of 5 average rating, 119 reviews
Guest favorite
The image captures a nighttime scene featuring a heated swimming pool with LED lighting. Nearby, a stylish cabin is illuminated with soft red light, showcasing its modern design. A hot tub is visible, surrounded by lush greenery and outdoor lights, creating a serene ambiance.
Cabin in Chesham

Romantic Christmas Retreat, Heated Pool, Hot Tub

Indoor spacesFamilyQuiet

4.99 out of 5 average rating, 343 reviews
Top guest favorite
A riverside log cabin is nestled among trees, featuring a spacious deck and seating area overlooking the water. Lush greenery surrounds the outdoor space, creating a natural setting that invites relaxation. The cabin’s wooden structure blends harmoniously with its peaceful environment.
Cabin in Reading

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

Indoor spacesFamilyAccuracy

4.98 out of 5 average rating, 466 reviews
Top guest favorite
An outdoor sauna is featured prominently on a wooden deck, illuminated by warm lighting. A hot tub is positioned beside the sauna, and the cottage's brick facade and chimney provide a cozy backdrop under a dusk sky.
Farm stay in Buckinghamshire

Farm stay in Buckinghamshire

Indoor spacesKitchenHeating

4.95 out of 5 average rating, 168 reviews