Holiday rentals with beach access in Isle of Portland

4.93 out of 5 average rating, 235 reviews

1888 Portland stone cottage

1888 Portland stone cottage, with many original features. Stone fireplace with log burner. Cosy 2 bedroom, 3 storey cottage located within easy walking distance of Easton Square, which has local amenities, including grocery stores, chemist, pubs and cafes. Small sunny aspect courtyard with bistro table and chairs. A perfect holiday location all year round, for either sun and relaxation, or enjoy activities like windsurfing, sailing, diving, rock climbing, fishing, walking and bird watching.

4.92 out of 5 average rating, 590 reviews

An open plan kitchen and living area is showcased, featuring a modern kitchen island with three high bar stools. The living space includes a comfortable sofa accented with several cushions, while large windows allow natural light to fill the room.

Apartment in Portland

1 Bed home near Sailing academy Portland, Weymouth

The home is located in Portland near to a Port and 5 miles to Weymouth also 10 min walk to sailing academy The area is noted for diving,windsurfing,fishing,sailing,extensive coastal walks,rock climming, cycle routes It is a one bedroom apartment.There is a small Beach and it’s a short walk to shops,cafe's and restaurants.Includes an open plan kitchen,living room and en-suite bathroom with electric showerThere is a sofa bed on request Parking is nearby but free parking is available in the street

A serene coastline is depicted at sunset, with the sun gently descending towards the horizon. The soft gradient of colors in the sky reflects on the quiet water, while a pebbled beach runs along the foreground, providing a peaceful natural setting.

4.89 out of 5 average rating, 196 reviews

Chesil Cove Holiday Cottage

A Grade II listed traditional characterful fisherman's cottage located adjacent to the iconic Chesil Cove on the isle of Portland, part of the Jurassic Coast. The cottage is small & cosy with two bedrooms, upstairs wetroom & modernised kitchen with solid wood breakfast bar. The wooden stairs are very steep & narrow so the property is not suitable for young children/those with mobility issues. An enclosed south-facing backyard is a suntrap for private sunbathing, drying swimming/diving gear etc.

4.91 out of 5 average rating, 141 reviews

A balcony with panoramic sea views is highlighted by a small dining set featuring four yellow chairs and a matching table. Sunlight illuminates the area, enhancing the inviting space for relaxation or meals.

Townhouse in Portland

Bright & beautiful 4 bedroom house with sea views

We're very excited to have installed a large balcony overlooking the sea, we hope you'll fall in love with Coastguard's Vantage as much as we have. Many of the rooms have sea views A 3min walk from Chesil Beach, it's the perfect base for experiencing the world famous walks We'll give you a guide about all the free parking spaces within 2mins walk from the house A utility room with washing machine & dryer has space to store boards, sails etc It's also close to the National Sailing Academy.

A cozy lounge area features a rustic stone fireplace with a log burner, surrounded by soft seating. A plush rug lies on the wooden floor, and framed pictures are hung on the walls. A staircase leads to the upper level.

4.91 out of 5 average rating, 268 reviews

Milly Moll Cottage, next to Church Ope Cove.

Julie and Matt welcome you to Milly Moll Cottage. A quirky C18th, grade 2 listed property full of character and charm, just next door to the Portland museum. Built of Portland stone with original fireplaces and a cozy lounge with a log burner, from here you can explore the Jurassic coast. It’s a 2 minute walk to Church Ope Cove, either passing under Rufus Castle arch or via the ruins of St Andrews church and is ideally placed for numerous outdoor pursuits. We hope you will enjoy your stay.

4.99 out of 5 average rating, 105 reviews

Home in Portland

Stone's Throw, Portland, on the Jurassic Coast

Stone's Throw is an open plan, modern house set in a residential development which was voted Supreme Winner of the Housing Design Awards. The development forms part of the 2012 Olympic legacy. Stone's Throw was home to the Trinidad and Bermuda Olympic sailing teams. The house is overlooking the green on Ben Ainslie Square and is a few minutes walk from Chesil Beach, Portland Castle, Marina, Sailing Academy, pubs and cafes. The Iconic Portland Bill lighthouse is a nearby visitor attraction.

Superhost

A historic three-story stone house is framed by blooming flowers in the foreground. The structure features large windows and a welcoming entrance, set against a clear blue sky, showcasing its charm and inviting atmosphere.

Townhouse in Portland

Historic Seaman Chaplaincy, Seaview All Rooms

The Gift House Portland is a historic Seaman's Chaplaincy, 3 storey late Georgian stone house. All 4 spacious bedrooms have sea view & perfect for sunset watching. Dog friendly (1dog only) Locate in island village, 5-8 mins walk to pebble beach, 17th century pub, restaurants, good coffee, good chippy & grocery shop. Jurassic coast walks, sculpture park, Portland stone quarry, cycling, swimming, rock climbing, sea fishing, diving, kayak, sailing, paddling, windsurf & more are around.

4.88 out of 5 average rating, 167 reviews

A view of Maidenwell Cottage from the garden, showcasing a landscaped area with palm trees and vibrant flowers. The cottage's exterior features a blue door and a stone wall, framed by greenery that enhances the inviting outdoor space.

4.99 out of 5 average rating, 336 reviews

Maidenwell Cottage. Near Chesil Beach, Portland

Maidenwell Cottage is a Grade II listed period property on Portland, the southernmost point of the Jurassic Coast that has been refurbished to a high standard and designed to make you feel at home. Chesil Beach, local shops, cafes and pubs are all a within a short walking distance. Maidenwell Cottage is perfect for families and couples looking for a cosy seaside retreat and those looking for a place to relax following a day of walking, climbing and water sports.

4.95 out of 5 average rating, 301 reviews

Townhouse in Portland

CLOUD 9 🦚 Homely & Happy 😊 Near the Beach 🌊🐟🌞

Welcome home, welcome to CLOUD9🌅 Vintage-modern velvet luxury in the historic heart of Fortuneswell on the Isle of Portland🌊 Fully renovated 2019-2022, & designed with love🧡 Living/dining room, kitchen, downstairs w/c, enclosed garden. Spacious shower room plus 3 themed bedrooms 🦚🌸 with light sea views⛵️ Chesil beach, co-op, fish & chips & pubs close-by🐟 😊 Super fast 100mb+ WiFi. Fully equipped kitchen. *If booking for 1-2, loft room will be locked.

4.87 out of 5 average rating, 212 reviews

A living area features light-colored furniture, including a cozy sofa adorned with decorative pillows. A flat-screen television sits on a dark wooden unit. Artwork depicting a sailboat and a wooden oar add character to the walls. Natural light enters through a window with light shades.

Home in Portland

Fair Winds House

Fair Winds offers a getaway just a stone's throw from the ocean and Portland Marina with allocated parking and enclosed garden. Wake up to sea views 2 minutes walk from Portland Castle Beach, or 5 minutes to the renowned Chesil Beach. We have a brilliant bakery and the beachside sauna, both just around the corner. For a peaceful retreat or an adventure by the sea, Fair Winds is an ideal base for exploring the wonders of Dorset's stunning coastline.

4.88 out of 5 average rating, 118 reviews

An aerial view of a contemporary property nestled within a coastal village, highlighting a long stretch of Chesil Beach in the background. The image captures the gentle curve of the beach, framed by various houses and rooftops under a clear blue sky.

Home in Portland

Chesil Beach Mews Cottage

Enjoy everything the Jurassic Coast has to offer, whatever the time of year. Situated literally a stone’s throw from the majestic Chesil Beach, this contemporary 3 bedroom, 2 bathroom property, with private parking, is perfect for exploring or relaxing. The property is set back from the main road within a modern private gated mews, so the only noise you will hear at night is the sound of the sea.