jolidays.co.uk jolidays.co.uk
Home Map Visits Stays App

Isle of Wight

A picturesque island with rich Victorian heritage, scenic coastlines, historic castles, renowned festivals, and excellent walking and cycling routes.

Fair Isle Holiday Cottages - Shannon

This contemporary detached holiday home built in 2024 offers spacious accommodation for up to 10 guests with 4 bedrooms and scenic south-facing countryside views near the island's capital.

celebration-feel family-focused child-friendly group-friendly

Old Coastguard Cottage

This former Victorian coastguard cottage offers cosy and homely accommodation near the beach, set in a tranquil location perfect for family holidays and coastal explorations on the Isle of Wight.

cosy homely laid-back private-retreat scenic fresh-air nature-immersion family-focused child-friendly country-walk-base outdoor-activities

Elm Cottage

Elm Cottage is a semi-detached holiday home located in the Undercliff area between the cliff and the sea, providing a micro-climate with Mediterranean flora and fauna, suitable for families or friends with beach access nearby and a private courtyard garden.

family-focused child-friendly private-retreat self-contained easy-stay scenic fresh-air nature-immersion

Olive

A circular hut designed for a romantic countryside escape with an open plan living space, private hot tub, fenced lawn with garden furniture, and peaceful rural surroundings near Ryde.

romantic private-retreat scenic nature-immersion countryside peaceful self-contained stylish

Monument House

This spacious 5-bedroom detached house in Totland Bay offers modern and elegant living with coastal and countryside views, accommodating up to 10 guests with pet allowance, private parking, garden and terrace spaces, and a hot tub available on request.

private-retreat family-focused child-friendly

Skipper's Rest

A charming and cosy period holiday home in East Cowes offering a family-friendly and dog-friendly atmosphere with two bedrooms, two living rooms, and an enclosed garden, ideally positioned for exploring the scenic and historic Isle of Wight.

cosy homely family-focused child-friendly country-walk-base scenic

Rew Farm Barns - Property 1

This offering is a period barn conversion set in a peaceful countryside courtyard near Ventnor with easy access to the beach and local attractions, providing a family-friendly and comfortable stay with garden and parking.

family-focused child-friendly

Coed Faen

Coed Faen is a three-bedroom property located in the coastal village of St Helens on the Isle of Wight, offering a peaceful setting with nearby village amenities and access to outdoor activities.

family-focused private-retreat outdoor-activities good-stopover scenic fresh-air country-walk-base

Brook Farmhouse Cottages - The Farmhouse

The Farmhouse is a tastefully converted historic building from 1820 offering accommodation over three floors with panoramic countryside views, situated near coastal attractions and local landmarks.

family-focused child-friendly group-friendly good-for-gatherings scenic countryside private-retreat homely stylish self-contained

Park Farm - Honeysuckle Cottage

A quaint two-bedroom barn conversion on the Isle of Wight, set in a peaceful rural location near beaches and local attractions, offering a homely and stylish retreat with private outdoor space and on-site parking.

peaceful homely private-retreat stylish couple-focused romantic self-contained scenic fresh-air nature-immersion countryside country-walk-base outdoor-activities family-focused

Trinity Bee

This contemporary second-floor apartment in Ventnor offers a compact and stylish living space with open-plan design, natural light from large arched windows, and views over hillside downs, located near the beach and town amenities on the Isle of Wight.

stylish

Fair Isle Holiday Cottages - Hill Top Cottage

Hill Top Cottage is a newly converted barn set in quiet rural countryside on the Isle of Wight, offering panoramic views and a peaceful retreat while being near the island's capital and local amenities.

peaceful cosy homely private-retreat easy-stay scenic fresh-air nature-immersion countryside country-walk-base family-focused child-friendly group-friendly

Plover Cottage

A charming and cosy restored Victorian cottage located near coastal walking paths and birdwatching areas, offering a quiet and private retreat suitable for families and small groups.

homely private-retreat child-friendly peaceful country-walk-base nature-immersion scenic fresh-air family-focused

Sunny South Lodge

Sunny South Lodge is a high-quality detached house located on the coastal path between Sandown and Shanklin, offering peaceful and romantic accommodation with scenic sea views and easy access to local amenities and transport.

private-retreat peaceful romantic self-contained scenic child-friendly

Moles Leap

Moles Leap is a self-contained annexe situated in the countryside near Sandown and Ryde, providing a peaceful holiday base close to sandy beaches, scenic walks, and family entertainment.

self-contained private-retreat family-focused child-friendly scenic countryside country-walk-base laid-back

White Haven

White Haven is a cosy ground floor apartment located in Lake near Sandown on the Isle of Wight, offering a peaceful seaside setting with easy access to local amenities and picturesque beaches, suitable for small families and groups up to four guests.

cosy family-focused child-friendly self-contained peaceful laid-back scenic waterside-feel fresh-air nature-immersion country-walk-base easy-stay

The Boathouse

This Grade II listed two-bedroom holiday cottage by the sea offers a bright and airy open-plan living space with waterside views, situated on the waterfront of the Isle of Wight with an enclosed lawned garden and convenient access to local attractions and outdoor activities.

peaceful cosy homely laid-back private-retreat romantic self-contained easy-stay scenic fresh-air waterside-feel water-activities family-focused child-friendly

Fort Spinney Holiday Bungalows - Bungalow 3

A cosy and homely bungalow on the Isle of Wight, close to the beach and surrounded by scenic natural beauty, providing a laid-back and family-friendly environment with easy ground-floor access and shared enclosed garden space.

cosy homely laid-back private-retreat easy-stay scenic fresh-air nature-immersion waterside-feel water-activities family-focused child-friendly

Merryweather Cottage

This Grade II listed, thatched holiday cottage with character features including beams and low ceilings offers far reaching countryside views and is located 15 minutes walk from a sandy beach near Bembridge village.

Shoreline Cottage

A charming Victorian former navy coastguard cottage on the sea front in Sandown with three bedrooms, three reception rooms, sea views, and an enclosed lawned garden, ideal for families with amenities nearby.

family-focused child-friendly cosy homely scenic fresh-air waterside-feel

Apple Tree Cottage

Apple Tree Cottage is a cosy detached chalet suitable for couples and pet friendly, located on the Isle of Wight with scenic views over Sandown Bay and access to a quiet beach via cliff top path, offering a peaceful and private retreat experience.

cosy couple-focused self-contained private-retreat scenic fresh-air nature-immersion outdoor-activities good-stopover easy-stay

Marina View

This stylish holiday home is located in a peaceful residential development near a scenic marina, offering nautical views and close proximity to local amenities and seaside resorts.

stylish peaceful scenic private-retreat self-contained easy-stay family-focused child-friendly

Hill Croft Cottage

Hill Croft is a spacious detached cottage located in a scenic Area of Outstanding Natural Beauty on the southern tip of the Isle of Wight, suitable for up to six guests including couples and families, with views over the English Channel and close proximity to coastal and countryside attractions.

peaceful homely private-retreat couple-focused family-focused child-friendly scenic fresh-air nature-immersion wildlife countryside country-walk-base outdoor-activities good-for-gatherings

The Old Cowshed

The Old Cowshed is a two-bedroom lodge set in a peaceful countryside smallholding near Thorness Bay beach on the Isle of Wight, offering a tranquil rural retreat with modern comforts and scenic outdoor spaces.

peaceful cosy homely laid-back private-retreat stylish romantic self-contained scenic fresh-air nature-immersion countryside country-walk-base outdoor-activities family-focused child-friendly

Brook Farmhouse Cottages - Palomino Cottage

Palomino Cottage is a one-bedroom cottage on the ground floor with a kingsize bed and an open plan living space that includes a sofa bed, located in a rural coastal setting on the Isle of Wight near various attractions and countryside.

pampering homely private-retreat romantic self-contained couple-focused child-friendly group-friendly peaceful scenic

Sandstones

An 18th-century stone cottage in the village of Niton, combining historic charm with modern amenities, set near the coast and countryside.

peaceful homely private-retreat stylish country-walk-base outdoor-activities family-focused child-friendly scenic self-contained

The Camber

A characterful 5-bedroom, 4-bathroom reverse-level townhouse in Cowes with scenic park and harbour views, close to ferry and amenities, featuring ample living space across five floors and an enclosed garden with patios.

family-focused child-friendly scenic countryside country-walk-base outdoor-activities good-for-gatherings homely functional private-retreat

The Hideaway

A high-specification ground floor one-bedroom apartment located in the peaceful countryside near Yarmouth, Chessell, offering a blend of modern living and charming hospitality in a tranquil setting with a private courtyard garden and nearby amenities.

private-retreat stylish countryside

Clarendon House

Clarendon House is a traditional, period family home near Shanklin Old Village and the sandy beach, offering a spacious and charming environment with a large enclosed patio and garden area for guests to enjoy.

family-focused child-friendly private-retreat peaceful country-walk-base scenic homely

Fair Isle Holiday Cottages - Fastnet

This detached, dog-friendly holiday home offers countryside views close to the island's capital, featuring ground-floor open plan living, three bedrooms, a balcony, wrap-around gardens, and private parking.

peaceful cosy homely laid-back private-retreat stylish self-contained family-focused child-friendly multi-generational country-walk-base nature-immersion

Westfield

A detached rural property suitable for up to 4 guests, located near a car ferry and within walking distance of a pub, offering exposure to wildlife and nature with a peaceful countryside setting.

peaceful cosy homely private-retreat laid-back child-friendly family-focused nature-immersion wildlife countryside country-walk-base good-for-gatherings

Longford Cottage

Longford Cottage is a newly refurbished holiday home situated in a picturesque village on the Isle of Wight, offering a rural setting close to the coast and local attractions.

cosy homely private-retreat stylish self-contained scenic fresh-air nature-immersion countryside country-walk-base family-focused child-friendly

Willow Barn

Willow Barn is a three-bedroom barn conversion set in a peaceful rural location with access to shared lawned garden areas and an enclosed patio, providing a cosy and homely atmosphere suitable for families and couples.

peaceful cosy homely laid-back private-retreat self-contained scenic fresh-air countryside country-walk-base family-focused child-friendly

The Shieling

This semi-detached coastal holiday home on the western Isle of Wight is a small, pet-friendly retreat ideal for couples, featuring open plan living, a small enclosed patio and private parking.

romantic couple-focused self-contained private-retreat peaceful scenic outdoor-activities

Island Retreat

This caravan accommodation is nestled in a lively holiday park setting offering cosy living space on the ground floor, ideal for a relaxed holiday with local amenities, a heated shared swimming pool, and close proximity to the scenic Isle of Wight attractions.

cosy family-focused child-friendly scenic fresh-air nature-immersion outdoor-activities

Brook Farmhouse Cottages - Dapple Cottage

Dapple Cottage is a homely and family-focused holiday cottage set in a scenic countryside and coastal location on the Isle of Wight, offering a peaceful private retreat with self-contained living spaces suitable for small groups or families including pets.

homely family-focused scenic countryside group-friendly self-contained private-retreat

Hampton House

Hampton House is a luxurious five-star detached house on the Isle of Wight with five bedrooms, private hot tub and swimming pool, private parking, and extensive outdoor and indoor leisure facilities in a peaceful award-winning village setting.

peaceful homely stylish indulgent private-retreat family-focused child-friendly celebration-feel scenic fresh-air nature-immersion waterside-feel water-activities outdoor-activities

Sea Breezes

Sea Breezes is a semi-detached holiday home located about 1 mile from the sandy beach at Totland, featuring a quirky layout with 3 bedrooms and 2 bathrooms across two floors, suitable for up to six guests including families with children and pets. The property includes an enclosed garden with patio, bike storage, and private parking for two cars, positioned in a scenic village ideal for coastal walks and beach activities.

family-focused child-friendly easy-stay peaceful scenic private-retreat

The Galley

The Galley is a warm and welcoming single-storey cottage on the Isle of Wight with panoramic countryside views, situated close to local attractions and amenities.

peaceful cosy homely laid-back private-retreat easy-stay scenic fresh-air nature-immersion countryside country-walk-base family-focused child-friendly

Fort Spinney Holiday Bungalows - Bungalow 5

This ground-floor bungalow in the village of Yaverland near Sandown offers a family-friendly seaside holiday close to the beach with sea views, enclosed gardens, and easy access to local attractions and watersports.

family-focused child-friendly fresh-air easy-stay

Kipper Cottage

Kipper Cottage is a detached ground-floor cottage with two bedrooms and en-suites, located by Wootton Creek with a large garden, coastal views, and a private jetty; it offers a peaceful coastal retreat suitable for romantic breaks and active holidays.

romantic private-retreat

Mulberry Lodge

This detached two-bedroom house offers a bright and airy coastal retreat with stunning sea views, located near beaches and local amenities, featuring a tranquil garden and private driveway parking.

peaceful scenic outdoor-activities family-focused private-retreat homely self-contained easy-stay

Sunnyside Lodge

This two-bedroom lodge on Fairways Holiday Park offers a comfortable ground-floor open-plan living space with a shared heated outdoor swimming pool and an on-site clubhouse, situated near coastal attractions on the Isle of Wight.

Grange Farm Holidays - The Coach House

The Coach House is a family-oriented cottage in the village of Wootton on the Isle of Wight set within a rural farm environment surrounded by ancient woodland and countryside, suitable for walkers, cyclists, and nature enthusiasts.

family-focused child-friendly activity-led nature-immersion countryside country-walk-base outdoor-activities group-friendly good-for-gatherings

The Old Kitchens

The Old Kitchens is a single-storey stone cottage on the outskirts of Totland Bay village, Isle of Wight, blending traditional character with modern comfort in a peaceful coastal countryside setting.

peaceful cosy homely private-retreat family-focused child-friendly scenic fresh-air nature-immersion countryside country-walk-base outdoor-activities

Seabreeze Retreat

This two-bedroom bungalow in Shanklin offers a comfortable and well-presented coastal retreat featuring a garden, patio, and easy access to Isle of Wight attractions and local amenities.

peaceful cosy homely laid-back private-retreat easy-stay scenic fresh-air nature-immersion countryside country-walk-base outdoor-activities family-focused child-friendly

Property 3

A stylish cottage on the Isle of Wight near Ventnor with four bedrooms and parking, featuring underfloor heating, smart TVs, a fully equipped kitchen, an enclosed garden, and a peaceful rural coastal setting.

stylish self-contained family-focused child-friendly

Littlehaven

This is a ground floor one-bedroom annexe accommodating up to 4 guests with stunning sea views near Ventnor on the Isle of Wight, designed to be accessible and pet-friendly, with a balcony and back garden, private parking for one car, and convenient location near local amenities and scenic outdoor activities.

peaceful cosy homely private-retreat scenic fresh-air nature-immersion family-focused child-friendly country-walk-base outdoor-activities

Cooks Castle Farm - The Dairy

The Dairy is a cosy and characterful former farm building set in an Area of Outstanding Natural Beauty on the Isle of Wight, offering a private and laid-back rural retreat with scenic countryside views and access to walking and cycling trails.

cosy homely laid-back private-retreat easy-stay independent-stay scenic fresh-air nature-immersion countryside country-walk-base outdoor-activities family-focused child-friendly functional

Hampton House

A luxurious Victorian villa overlooking a picturesque West Wight beach, set across multiple floors with family-friendly and pet-friendly features in a scenic waterside location.

family-focused child-friendly self-contained private-retreat scenic waterside-feel good-stopover country-walk-base outdoor-activities

Location

Similar pages
  • Isle of Wight (pet-friendly, family)
Last update: 12 June 2026
© jolidays.co.uk
Home Privacy