
House holiday rentals in Isle of Portland
Find and book unique houses on Airbnb
Top-rated house rentals in Isle of Portland
Guests agree: these houses are highly rated for location, cleanliness and more.

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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Guests Favorite Coastal Cottage, walk to beach
Our cottage is on the southwest coastal path, a couple of minutes walk to the beach and sleeps 7. It's dog-friendly, free parking & ideally located to enjoy family holidays and watersports with safe beaches for swimming. Quiet tranquil area but near enough for each access to all the main attractions. Bedroom 3 can either be a king-size bed or set up as a twin with two single beds. It looks onto safe green areas for children & dogs to play. The cottage is well equipped. Saltpath_cottage
FamilyLocationLong stay

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.
LocationFamilyHiking

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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Cottage 5 mins walk to Harbour
Your family will be close to everything when you stay at this centrally-located cottage. Coral Cottage is only 5 mins walk to the harbour & town and 10mins walk to Weymouth’s blue flag Sandy beach. Coral Cottage has been refurbished to a very high standard and as a former Victorian railway cottage it is full of character and is a perfect retreat for families or couples. It is ideally situated for the harbour, marina, beach, cafes and shops, with a nearby supermarket to hand.
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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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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!)
ValueLocationNearby

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.
LocationFamilyCleanliness

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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Spacious Caravan near sea Weymouth Bay Haven
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East Creek, beach, pool, dog, hot tub - Ringstead
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The Lindens
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Stunning Home with Roof Terrace at Silverlake
LocationFamilyPets

The Lookout - Rooftop hot tub, bar, pool table
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Luxury Lakeside Retreat with Hot Tub- sleeps 12-14
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Susie's Caravan in Dorset
LocationFamilyBeach
Weekly house rentals

Enchanting Manor Coach House
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Totally Unique 6 Double Bedroom Manor House Poole.
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Schooner Cottage
ValueLocationCondition

Spacious luxury home | 200m from beach | parking
ValueFamilyQuiet

BillWatch Cottage
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Sunset Cottage
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Beautiful cottage with sea views & sunsets
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1GB Wifi | SuperKing bed | Sport TV | Washer/Dryer
ValueFamilyQuiet
Private house rentals

Seaview Home w/Private Garden,BBQ,Decking,Fire Pit
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Sally Hall ⭐️Large central Portland home
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Cove Cottage: minutes to sea, and sunset views
ValueFamilyWalkability

2Houses and a Chapel by the sea
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Fisherman’s cottage on Chesil Beach
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Mariners Cottage
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Luxury Coastal Bolthole · Hot Tub · Beach Access
LocationValueIndoor spaces

Harbourside Townhouse - Sleeps 8
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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
- Kimmeridge Bay
- Bournemouth International Centre
- Beer Beach
- West Bay Beach
- Alum Chine Beach
- Shorefield Country Park
- Highcliffe Beach
- Crealy Theme Park & Resort
- Poole Quay
- Powderham Castle
- Mudeford Sandbank





