Vacation rentals with outdoor seating in Isle of Portland

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Top-rated outdoor seating rentals in Isle of Portland

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Guest favorite

Cottage in Portland

4.81 out of 5 average rating, 118 reviews

Sea View Cottage, Portland

Sea View Cottage is part of a 200+ year old former Portland stone merchant's house just a few minutes walk from the sea, with sea views from the living room and all bedrooms and (best of all) the sea facing sun deck which gets the sun most of the day. The property sleeps 4 and has a ground floor lounge with woodstove, dining area with adjacent workspace, well equipped kitchen, and bathroom with large electric shower, first floor bedroom (double bed), and second floor bedroom (two single beds).

Jan 31 – Feb 7

G$34,156 GYD per night

Guest favorite

Guesthouse in Dorset

4.96 out of 5 average rating, 113 reviews

Seaside studio cabin minutes from 'secret' beach

Tucked away up an unmade track & five minutes walk from a 'secret' local beach; Cove Cabin is a compact, stylish, private space; perfect for a couple or two companions. On the doorstep of lesser known beaches & gardens but not far from Weymouth's bustling scenic harbour & golden sands. Ideal stop off whilst walking the SW Coast Path. The perfect area for watersports, wild swimming, walking, mooching around the harbour & locality, sampling the local seafood & eateries & just simply relaxing.

Jul 1 – 8

G$25,993 GYD per night

Guest favorite

Cottage in Dorset

4.98 out of 5 average rating, 210 reviews

Fabulous Coastal Cottage In Portland, Dorset

Welcome to our lovely, warm family holiday home. Our coastal cottage looks small from the outside but can accommodate up to eight guests and is fantastic for getaways with family or friends. With some sea views and close to the south west coastal path, the cottage is a great place to explore Portland and the surrounding area. Being a 10 minute walk from Portland Marina and Chesil Beach, it’s the perfect spot to indulge in Sailing, Bird Watching, Diving, Kayaking and other outdoor activities.

Apr 16 – 23

G$51,371 GYD per night

Superhost

Cottage in Portland

4.89 out of 5 average rating, 129 reviews

Number 107, Isle of Portland, Dorset

Number '107' positioned on the Isle of Portland with its close proximity to Chesil Beach is a spacious, comfy & well equipped cottage within 5 mins walk of the beach. Situated close to all local amenities with shops, cafes & pubs all within a short walking distance. The cottage is perfect for families & couples looking for a cosy seaside retreat & those looking for a place to relax after a day of walking, climbing, and water sports. An ideal base for exploring Jurassic Coast and beyond.

Oct 14 – 21

G$27,564 GYD per night

Guest favorite

Cottage in Easton

4.92 out of 5 average rating, 166 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.

Oct 15 – 22

G$25,601 GYD per night

Guest favorite

Tiny home in Portland

4.94 out of 5 average rating, 190 reviews

Coast - White Stones Studios

Come and enjoy our new and unique contemporary eco-friendly accommodation set in peaceful and creative surroundings at the heart of Easton, Portland, on the tip of The Jurassic coast. Located to the rear of White Stones Art Cafe's secluded and tranquil gardens there are three holiday studios available, each sat nestled together in peaceful surroundings. Breeze is one of our three bespoke holiday studios, finished to a high standard and providing a contemporary holiday experience.

Jan 12 – 19

G$23,043 GYD per night

Guest favorite

Cottage in Dorset

4.92 out of 5 average rating, 135 reviews

Chesil Cove Holiday Cottage

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

Jul 1 – 8

G$25,035 GYD per night

Guest favorite

Shepherd’s hut in West Bexington

4.97 out of 5 average rating, 347 reviews

The Seaside Shepherd’s Hut

Fall asleep to the sound of waves on shingle in this stunning, hand-crafted oak shepherd’s hut. In winter the Hut is cosy with double glazing, a wood burner plus radiator. In summer relax on the deck to enjoy glorious views of Lyme Bay in an AONB on the World Heritage Jurassic Coast. Nestling in the garden, Chesil Beach and the South West Coast Path are 30 seconds away down a private path. Watch magnificent sunsets over the bay and enjoy stargazing in our dark skies.

Dec 2 – 9

G$28,912 GYD per night

Guest favorite

Cottage in Fortuneswell

4.98 out of 5 average rating, 186 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, 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.

Mar 9 – 16

G$33,167 GYD per night

Guest favorite

Cottage in Dorset

4.98 out of 5 average rating, 312 reviews

The Condo (Indoor Pool available May-Oct only)

Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!

Mar 5 – 12

G$26,985 GYD per night

Guest favorite

Barn in Winfrith Newburgh

4.99 out of 5 average rating, 272 reviews

The Stable Barn - Luxury Spacious Cottage for Two

The Stable Barn is a comfortable, centrally heated cottage with split level interior and sculptured mezzanine. It provides extremely spacious open-plan accommodation for two. Wifi - Superfast fibre To the rear of the barn is a partly walled garden laid to lawn and gravel with clipped hedges and shrubs. The cottage is equipped with a sprinkler system, smoke detector, and carbon monoxide detector. Superfast fibre broadband and Smart TV.

Oct 21 – 28

G$25,891 GYD per night

Guest favorite

Tiny home in Weymouth

4.85 out of 5 average rating, 142 reviews

Cosy Sail Loft on the harbour.

This special place is close to everything, making it easy to plan your visit. With your own parking space, own entrance, bedroom / lounge, own kitchen and Bathroom, you can be fully self sufficient or enjoy all the local pubs and restaurants on your door stop. Literally right on the harbour front and only a minute away from the beach, this cosy property allows you to enjoy all of this seaside town within a few minutes.

Jan 15 – 22

G$18,189 GYD per night