50 Best Vacation Rentals in Isle of Portland - Holiday Lettings - Cabins

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Isle of Portland

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386 Vacation rentals

(16) Very Good 

Certificate of Excellence

20

Vacation cottage rental

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Seagull Cottage is a lovely holiday house ideal for sailing, beach, and outdoor activity holidays in Portland. It is located just one mile from the Weymouth and Portland National Sailing Academy (WPNSA), the 2012 Olympic Sailing venue. Chesil beach is just a few minut …see more

Certificate of Excellence

from $126 / night

$854 - $1,036 / week

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Responds fast!
avg. 2 hours 34 minutes

from $126 / night

(29) Very Good 

Certificate of Excellence

31

Vacation studio in Isle of Portland

Dorset / Isle of Portland

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
A VERY MODERN HOLIDAY LET STUDIO APARTMENT LOCATED IN A QUIET POSITION ON THE ISLE OF PORTLAND NEAR WEYMOUTH IN THE HEART OF DORSET, ON THE COAST OF SOUTH WEST ENGLAND. SUITABLE FOR SINGLE OR DOUBLE OCCUPANCY. FACILITIES INCLUDE FLAT SCREEN TV, DVD PLAYER, MICROWAVE, …see more

Certificate of Excellence

from $66 / night

$413 - $490 / week

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from $66 / night

5

Vacation home in Isle of Portland

Dorset / Isle of Portland

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Pet friendly
Lyndhurst is a four bedroomed house opposite Victoria Gardens and a short walk from Chesil Beach. Downstairs you will find two family rooms, one with a TV and the other for quiet moments. The kitchen, which overlooks the outside decking area, is spacious and sports a …see more

from $210 / night

$1,540 / week

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from $210 / night

(2) Excellent 

15

Isle of Portland Vacation apartment accommodation

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Marina View Apartment is a stunning modern apartment located overlooking Portland Marina and Harbour on the Isle of Portland, Dorset. The modern accommodation on two floors is well presented and offers three spacious bedrooms. Use of indoor pool and great as a base fo …see more

from $173 / night

$833 - $1,631 / week

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from $173 / night

(21) Very Good 

Certificate of Excellence

40

Isle of Portland Vacation cottage rental

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly
Fishermans Cottage is a charming detached 18th century cottage on the edge of Southwell, with excellent sea views. Recently renovated with full central heating throughout and Wi Fi. On the ground floor there is a lounge / diner with sea view, a reception room, a fully …see more

Certificate of Excellence

from $126 / night

$553 - $1,428 / week

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Responds fast!
avg. 2 hours 35 minutes

from $126 / night

(50) Excellent 

Certificate of Excellence

17

Vacation home rental

Dorset / Isle of Portland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Ideal for small groups, couples & families - fabulous rural and sea views. A contemporary spacious detached house with a safe, secluded and walled garden. Situated in a prime position with spectacular rural and sea views looking towards Dorset's Jurassic Coast. Sle …see more

Certificate of Excellence

from $196 / night

$1,176 - $1,862 / week

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Responds fast!
avg. 23 minutes

from $196 / night

(3) Very Good 

14

Chalet rental in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
PET Friendly! A two-bedroom bungalow set in a unique coastal park offering total relaxation and fantastic sea views. The site is ideal for a place to rest your head after a day on the water or if you are looking for a relaxing quiet break by the sea. This holiday home f …see more

from $119 / night

$569 - $1,102 / week

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from $119 / night

(18) Very Good 

Certificate of Excellence

9

Isle of Portland Vacation home rental

Dorset / Isle of Portland

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Pebbles view is a Victorian Portland stone built mid terrace cottage in the village of Fortuneswell Portland offering stunning panoramic sea views of the Jurassic coasts Chesil beach from all floors The newly refurbished cottage arranged over three floors comprises …see more

Certificate of Excellence

from $126 / night

$910 / week

Book View

from $126 / night

(2) Very Good 

18

Isle of Portland Vacation home rental

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Suitable for children age 5+
This lovely family house is located in a perfect spot to offer the best of both worlds, a semi detached Edwardian cottage down a quiet lane leading to the beach and cliffs and just 10 minutes walk away from shops, cafes and other amenities. The ground floor offers com …see more

from $140 / night

$980 - $1,890 / week

Inquire View

from $140 / night

(19) Very Good 

Certificate of Excellence

21

Vacation cottage in Isle of Portland

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Pebble Reef is a traditional Quarryman's Cottage, full of character but lovingly renovated to include all the modern comforts you need. The cottage sleeps up to six people in 3 comfortable bedrooms. Upstairs there's one double with en-suite shower room, a twin b …see more

Certificate of Excellence

from $112 / night

$490 - $1,288 / week

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Responds fast!
avg. 2 hours 35 minutes

from $112 / night

(10) Very Good 

Certificate of Excellence

8

Vacation bungalow in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
A comfortable terraced bungalow with lounge/diner, kitchen and patio area in grounds near to Pennsylvania Castle so ideal for anyone attending functions there. Portland is a nature lovers paradise particularly of interest to birdwatching enthusiasts also to sailors as t …see more

Certificate of Excellence

from $105 / night

$980 / week

Book View

Responds fast!
avg. 49 minutes

from $105 / night

(38) Excellent 

Certificate of Excellence

19

Home rental in Isle of Portland

Dorset / Isle of Portland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
A contemporary, spacious house with private off-road parking. Situated in a central position on the lower part of the island, makes it ideal for guests visiting the Weymouth and Portland National Sailing Academy or the Jurrassic Coastline. Ideal for small groups, coup …see more

Certificate of Excellence

from $182 / night

$980 - $1,526 / week

Book View

Responds fast!
avg. 23 minutes

from $182 / night

(1) Excellent 

11

Isle of Portland Vacation home accommodation

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
150 Year Old Portland Stone Fisherman's Cottage. Two leather sofas to seat six. Freeview T.V. Books. DVD's. C.D's. Games .Wifi. There is a wood burning stove for the winter months and barbeque and alfresco dining during the summer months. Vintage pine dining table …see more

from $119 / night

$630 - $1,036 / week

Book View

Responds fast!
avg. 1 hour 59 minutes

from $119 / night

11

Home rental in Isle of Portland

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
This lovely holiday home sits in the heart of Fortuneswell, Portland a short stroll from the Jurassic Coast. Sea views can be seen from the property where in the evening the rear windows provide lovely sunset viewing. The owners of the property have made this holiday p …see more

from $150 / night

$724 - $1,413 / week

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from $150 / night

(1) Excellent 

8

Vacation home in Isle of Portland

Dorset / Isle of Portland

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Whether you are looking for that relaxing break, or here to sail or just time with the family this charming cottage would suit your needs. Nestled off Wakeham, you will agree this cottage is a real find. A charming cottage nestled just behind Wakeham, backing on …see more

from $161 / night

$779 - $1,522 / week

Book View

from $161 / night

(1) Good 

15

Isle of Portland Vacation studio accommodation

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 3 mi
  • Suitable for children age 5+
If you are looking for the perfect place for a romantic weekend break for two, a longer get-away-from-it-all holiday or fun time with a group of friends then you've found it! Every apartment combines quality overnight comfort and en-suite facilities with modern self-ca …see more

from $83 / night

$559 / week

Book View

Responds fast!
avg. 3 hours 43 minutes

from $83 / night

(6) Excellent 

17

Vacation home in Isle of Portland

Dorset / Isle of Portland

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
A beautifully presented character house with views over Chesil Beach and Portland Harbour. This holiday home has many character features and really is a home from home. The property has a single parking space, there is also ample on road parking and a covered 'alfresc …see more

from $154 / night

$742 - $1,449 / week

Book View

from $154 / night

(8) Excellent 

22

Vacation studio in Isle of Portland

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 3 mi
  • Suitable for children age 5+
Self contained apartment base on Southwell business park , isle of Portland. A short stroll from famous Portland bill& Jurassic coastline. Come &see for yourself Towels,Linens ,Toiletries provided equipped with hair dryer,iron+board ,fridge,toaster,kettle,Microwave ov …see more

from $49 / night

$336 - $420 / week

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Responds fast!
avg. 3 hours 43 minutes

from $49 / night

8

Isle of Portland Vacation cottage rental

Dorset / Isle of Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Charming three bedroom cottage ticked away a pebble's throw from Chesil Beach. Coral Cove is found between Sea View and Coastguard Cottages at the north end of the island. Ideal as a base for sailing, walking, diving and exploring the island and the rest of the county …see more

from $122 / night

$580 - $1,123 / week

Book View

from $122 / night

(32) Very Good 

30

Vacation cottage rental

Dorset / Isle of Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
A beautiful restored Victorian terraced cottage, on a quiet street in the village of Fortuneswell on the Isle of Portland, only 5 minutes walk from the famous Chesil Beach and part of Dorset's glorious Jurassic Coast. 5 min drive from National Sailing Academy. This fo …see more

from $112 / night

$602 - $1,148 / week

Book View

Responds fast!
avg. 3 hours 16 minutes

from $112 / night

(4) Very Good 

12

Vacation cottage in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Built in the 1800's, this sweet little original Portland stone Fisherman's cottage promises a lovely holiday experience.Artist Cottage sleeps four people in two bedrooms and has been delightfully restored.The cottage is found in Fortuneswell just five minutes from the N …see more

from $111 / night

$525 - $1,014 / week

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from $111 / night

11

Vacation home in Isle of Portland

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
This lovely holiday home sits in the heart of Fortuneswell, Portland a short stroll from Chesil Cove. Sea views can be seen from the property where in the evening the rear windows provide lovely sunset viewing. The owners of the property have made this holiday property …see more

from $168 / night

$1,176 / week

Book View

from $168 / night

(2)  

8

Vacation apartment in Isle of Portland

Dorset / Isle of Portland

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Ask about pets
Studio Apartment situated on 2nd Floor , Maritime House, Southwell Business Park, Portland .(ex mod building converted to living accommodation with kitchenette & en-suite bathroom) . Local amenities are within 5-10 mins driving distance. Approx 10 minutes walks from fa …see more

from $49 / night

$336 - $420 / week

Book View

Responds fast!
avg. 3 hours 43 minutes

from $49 / night

(1) Excellent 

15

Vacation cottage in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
A charming Portland Stone Cottage in the heart of Fortuneswell. Tastefully decorated and furnished it offers cosy accommodation, for four people. Public parking close by and you are just a short stroll from Chesil Beach, if you turn in the other direction and head up th …see more

from $107 / night

$507 - $979 / week

Book View

from $107 / night

(10) Very Good 

14

Isle of Portland Vacation home rental

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Car not necessary
This well presented holiday house has a large and sociable open plan living area with kitchen, seating and dining areas, allowing for a relaxed and inclusive holiday atmosphere. There are four bedrooms, a bathroom and a shower room. The ground floor provides two twin ro …see more

from $173 / night

$833 - $1,631 / week

Book View

from $173 / night

6

Penthouse rental in Isle of Portland with shared pool

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
This luxury 7th floor apartment at 199 Atlantic House is part of the prestigious Ocean View complex in Portland, Dorset. The apartment has been rated as 4* by the AA and overlooks Weymouth Bay and Portland Marina and is less than a mile from the National Sailing Academy …see more

from $175 / night

$840 - $1,960 / week

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from $175 / night

10

Home rental in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
This centuries-old cottage is in Easton, a village at the heart of the peaceful island of Portland. Easton has a good selection of shops, friendly pubs, cafes and a children's play area. Dunsubbin is a short walk from the atmospheric Church Ope Cove with its "smuggler …see more

from $145 / night

$583 - $1,130 / week

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from $145 / night

(5) Excellent 

22

Vacation home in Isle of Portland

Dorset / Isle of Portland

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Bayview has beautiful sea and coastal views in all directions. There are extensive coast and country walks from the door and a number of local coves and beaches with safe swimming, in particular Weymouth. Portland Harbour is famed for its water sports and was the venue …see more

from $120 / night

$840 / week

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from $120 / night

17

Vacation home rental

Dorset / Isle of Portland

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 6 mi
  • Child friendly
  • Pet friendly
Wavecrest is in the village of Fortuneswell, overlooking Chesil Beach and close to the Weymouth and Portland Sailing Academy and Windsurfing Centre. Perfectly located for sailors, windsurfers, divers, walkers and cyclists with storage for boards, sails, bikes and wetsui …see more

from $120 / night

$705 - $1,234 / week

Book View

Responds fast!
avg. 3 hours 31 minutes

from $120 / night

(1) Excellent 

10

Isle of Portland Vacation cottage rental

Dorset / Isle of Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Three bedroom Portland Stone cottage over three floors with fabulous views over Chesil Beach and The Fleet. Just a short walk from Chesil Beach. Divers, sailors, walkers and families will love this cottage. WiFi and TV included but you will be busy watching the sunse …see more

from $124 / night

$587 - $1,139 / week

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from $124 / night

(9) Excellent 

12

Cottage rental in Isle of Portland

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
A spacious, comfortable cottage in this pretty road, a short walk down to Chesil Beach and Cove, and being in a convenient position for The National Sailing Academy and Portland Harbour. A four bedroom cottage over three floors with views over Chesil Beach. There is a p …see more

from $154 / night

$742 - $1,484 / week

Book View

from $154 / night

(3) Very Good 

22

Vacation home in Isle of Portland

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
The house is a late Georgian stone house located in the middle of island village, facing the sea. All 4 double bedrooms, the lounge and dining room are having panoramic sea view. The house is fully equipped self catering and has everything you need for an unforgettable …see more

from $245 / night

$1,715 / week

Book View

Responds fast!
avg. 1 hour 20 minutes

from $245 / night

(2) Good 

8

Vacation home in Isle of Portland

Dorset / Isle of Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0 mi
  • Child friendly
  • Pet friendly
Portland Stone detached house backing onto Chisel Beach. 3 bedrooms, gas central heating, large bathroom on the first floor, and ample parking for two cars. Ideal for sailing holidays, dog walkers, in fact anyone who wants to make use of all that Portland has to offer. …see more

from $105 / night

$490 - $910 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from $105 / night

8

Isle of Portland Vacation cottage rental

Dorset / Isle of Portland

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
4 Sea View offers the best of modern comforts with period character in a cottage just a short walk from the splendors of Chesil Beach & Cove on the Isle of Portland Dorset. Offering a fabulous kitchen and comfortable accommodation. A character cottage desi …see more

from $140 / night

$670 - $1,305 / week

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from $140 / night

8

Vacation home rental

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
A sea side cottage situated a short stroll from Chesil beach and the Cove Inn, at the heart of Fortuneswell within a short distance of the Jurassic Coastline and National Sailing Academy at Portland Harbour. At the front of the property is an ideal place to relax with …see more

from $129 / night

$616 - $1,196 / week

Book View

from $129 / night

(10) Very Good 

Certificate of Excellence

8

Cottage rental in Isle of Portland

Dorset / Isle of Portland

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 3 mi
  • Car not necessary
  • Air conditioning
The Portland Hideaway is a 4* self contained self catering unit with open plan living space.It benefits from a fully equipped kitchen,separate shower room with wc & sink,open plan bedroom/lounge area with ample seating on the reclining leather sofa's & air conditioning …see more

Certificate of Excellence

from $70 / night

$455 - $595 / week

Book View

Responds fast!
avg. 1 hour 52 minutes

from $70 / night

20

Vacation apartment in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Ocean Views perched in an enviable position on Portland's seafront, situated on the Jurassic coast beside Chesil Beach. The apartments have been finished to a high standard with high quality flooring, wooden decked balconies and polished granite worktops. The developmen …see more

from $75 / night

$527 - $1,508 / week

Inquire View

from $75 / night

(1) Very Good 

18

Vacation apartment in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Enjoy contemporary living in a beautiful setting at 50 Ocean Views. This bright, open plan apartment is found on the second floor of the Ocean Views development in Portland, and with a spacious design and an onsite swimming pool and fitness centre, it's the perfect plac …see more

from $93 / night

$650 - $1,594 / week

Inquire View

from $93 / night

(5) Very Good 

16

Vacation apartment in Isle of Portland

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
82 Ocean Views is a stylishly furnished apartment with partial sea views, located on the fourth floor of the development, in an enviable position on Portland's seafront. The apartment has been finished to the highest standard with high quality flooring and polished gran …see more

from $75 / night

$527 - $1,519 / week

Inquire View

from $75 / night

(9) Very Good 

18

Vacation apartment rental

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Situated on Portland's scenic seafront with the famous Chesil Beach almost on your doorstep is 105 Ocean Views, a contemporary and stylish two bedroom apartment. With sophisticated furnishings and plenty of space for a group of four, this will make a wonderful getaway f …see more

from $93 / night

$650 - $1,672 / week

Inquire View

from $93 / night