
House holiday rentals in Isle of Portland
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Top-rated house rentals in Isle of Portland
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Blue Skies Retreat,Modern house Chesil Beach
Modern semi-detached house located two minutes walk from Portland Marina and Chesil beach. Perfectly situated for divers, walkers sailors and anyone who pursues water based activities. Pubs restaurants and takeaways within walking distance of the house. Private parking situated at the front of the property. This house has a modern contemporary interior with two double bedrooms. One of these with twin beds. Enclosed rear garden with patio and seating area perfect for watching the Chesil sunset.
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Stonehouse - a big beautiful house with sea views
Stonehouse is a big, rustic and beautiful seaside home for families and friends. It lies in the heart of the conservation area of old stone houses in Chiswell on the west coast. A stone's throw from the beach with great sea views. Walking distance to nearly everything - good coffee, a 17th century stone pub by the sea, seafood restaurant, home cooking, great ales, local shops, coastal walks, swimming and more. Kayaking, sailing, paddleboarding, rock climbing, horse riding and cycle hire.
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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.
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Charming Portland house with sea and sunset views
Welcome to our renovated Dorset getaway. Our Portland stone house is 5 minutes walk from Chesil Beach and 20 minutes walk to the Weymouth & Portland National Sailing Academy. The Isle of Portland is an idyllic spot to relax with stunning sea views or base yourself to explore the many activities in the area: walking, coasteering, horse riding, sailing, water sports, alpacas etc. The house is perfect for a self catering getaway but there are great restaurants a short walk away.
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Portland Stone Cottage on Chesil Beach
Three storey house with a recently refurbished kitchen. Neutral decor, plenty of space for a large family, outdoor patio with seating area, two TVs, central heating throughout, fridge/freezer, washing machine, bathroom with bath/shower, separate toilet. 1st floor: Double bedroom with TV and a single bedroom . 2nd floor: large bedroom with a double and single bed. A stone's throw away from Chesil beach, supermarket nearby, on the bus route, sea views and a peaceful neighbourhood.
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The Palms at No10 - Spacious and Family Friendly
Welcome to the Palms at No10! Unwind in this stylish and beautifully appointed home for your stay on the Jurassic Coast. The property offers ample space for 6 guests across three stunningly finished bedrooms, and our outdoor terrace provides al fresco to unwind after a day exploring everything Dorset has to offer. The Palms is perfectly located for a coastal getaway, with both the town centre just a short 20 minute walk away and the seaside only a stones throw away.
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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.
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Quiet Harbour Retreat | Sea Swim & Coast Path
A modern, spacious house forming part of the award-winning Olympic Village built in 2012. Set in a quiet square, minutes from Chesil Beach, a world-renowned geological landmark famous for dramatic scenery and year-round sunsets, and close to Portland Marina. Calm harbour swimming, a beachside sauna, yoga studio, spa facilities, leisure centre with pool, Jurassic Coast cliff walks, Portland Castle and the Portland D-Day Centre are all a short walk away.
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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.
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Character 4 bedroom house, Weymouth Harbour
Hartlebury End... your stunning home from home just a few minutes walk from Weymouth's outer harbour, town & beautiful sandy beach. Own car port & lovely enclosed garden. (I have 2 Airbnb's and the other one is on the harbourside, smaller and pet friendly so that will explain the reviews!)
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April's Cottage, sea views close to Chesil Beach
Escape from it all in this little cosy character cottage crammed with history and home comforts including own parking right outside your front door (size of parking space 3 x 5m). Located in the heart of the Jurassic coast, moments from Chesil Beach, local shops, pubs and cafes.
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Top To Bottom beautiful cottage heart of Easton
My place is close to great views, restaurants and dining. You’ll love my place because of the location, the people, the outdoors space, and the neighbourhood. My place is good for couples, families (with kids), big groups, and furry friends (pets).
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Popular amenities for house rentals in Isle of Portland
House rentals with a pool

Cosy Chesil Beach Getaway - Weymouth *no fees!*
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Pony View Lodge
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Spacious Caravan near sea Weymouth Bay Haven
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East Creek, beach, pool, dog, hot tub - Ringstead
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The Lookout - Rooftop hot tub, bar, pool table
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Stunning Home with Roof Terrace at Silverlake
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Luxury Lakeside Retreat with Hot Tub- sleeps 12-14
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Farmhouse sleeps 12 with indoor pool and sauna
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Weekly house rentals

Cottage 5 mins walk to Harbour
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Boutique Harbour Stay - walking distance to Beach
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Spacious luxury home | 200m from beach | parking
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Enchanting Manor Coach House
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BillWatch Cottage
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Beautiful cottage with sea views & sunsets
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1GB Wifi | SuperKing bed | Sport TV | Washer/Dryer
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Sunset Cottage
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Private house rentals

Mariners Cottage
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Sally Hall ⭐️Large central Portland home
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Luxury Coastal Bolthole · Hot Tub · Beach Access
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Stonehall House - a big and beautiful seaside home
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C Side House
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2Houses and a Chapel by the sea
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Fisherman’s cottage on Chesil Beach
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Lovely Holiday Home, opp Church Ope Cove, Portland
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Destinations to explore
- Waterfront rentals Isle of Portland
- Pet-friendly rentals Isle of Portland
- Rentals with breakfast Isle of Portland
- Townhouse rentals Isle of Portland
- Beachfront rentals Isle of Portland
- Cottage rentals Isle of Portland
- Family-friendly rentals Isle of Portland
- Rentals with beach access Isle of Portland
- House rentals England
- House rentals United Kingdom
- New Forest National Park
- Bournemouth Beach
- Weymouth Beach
- Paultons Park Home of Peppa Pig World
- Longleat Safari Park
- Southbourne Beach
- Boscombe Beach
- Mudeford Quay
- Brixham Harbour
- Durdle Door Holiday Park
- Torquay Beach
- The Tank Museum
- Lyme Regis Beach
- Bournemouth International Centre
- Kimmeridge Bay
- Beer Beach
- West Bay Beach
- Alum Chine Beach
- Shorefield Country Park
- Highcliffe Beach
- Powderham Castle
- Crealy Theme Park & Resort
- Poole Quay
- Mudeford Sandbank





