Watersports holiday villas and apartments Portland | Holiday Lettings

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  • Dorset
  • Isle of Portland
  • Portland

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32 Holiday homes

Filters applied: Water sports (32)

(8) Excellent 

1 / 32

Fishermans Cottage - Portland cottage sleeps 6

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 12 km; Great for children of all ages ;
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

from £85 / night

£350 - £995 / week

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from £85 / night

(10) Very Good 

1 / 20

Seagull Cottage - Portland cottage sleeps 4

England / Dorset / Isle of Portland / Portland

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Great for children of all ages ;
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

from £90 / night

£595 - £695 / week

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from £90 / night

(20) Very Good 

1 / 8

fishermans view - Portland cottage sleeps 4

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 47 nights min stay

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.2 km; Suitable for children age 5+;
Cottage with sea views over beautiful famous Chesil Beach. South facing patio with sea view. Accommodates up to four . Weekly change over Saturday. Dogs welcome and most places are dog friendly. Nearest beach approximately 200 metres. Minutes from excellent bus servic  …see more

from £40 / night

£280 - £580 / week

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from £40 / night

(11) Very Good 

1 / 20

Pebble Reef - Portland cottage sleeps 6

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Great for children of all ages ;
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  …see more

from £75 / night

£325 - £895 / week

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from £75 / night

(20) Very Good 

1 / 31

BEAUTIFUL STUDIO APARTMENT - OCEAN VIEWS,PORTLAND

England / Dorset / Isle of Portland / Portland

StudioSleeps 23 nights min stay

  • Studio
  • Sleeps 2
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Not suitable for children;
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

from £47 / night

£295 - £365 / week

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from £47 / night

(38) Excellent 

1 / 24

Church Ope Studio - Portland studio sleeps 2

England / Dorset / Isle of Portland / Portland

StudioSleeps 23 nights min stay

  • Studio
  • Sleeps 2
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Not suitable for children;
4 star studio on the Jurassic coast path at Church Ope Cove Portland Dorset. Spectacular view of the sea through ancient Rufus castle arch. Romantic hideaway for 2, a cosy retreat for walkers, work or leisure. Church Ope Studio is open all year. Wood burner. Wifi. Lu  …see more

from £53 / night

£325 - £395 / week

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from £53 / night

(32) Excellent 

1 / 19

65 Fortuneswell - 180° Sea Views from Balcony

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Great for children of all ages ;
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

from £100 / night

£760 - £1230 / week

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from £100 / night

(40) Excellent 

1 / 17

Quarries Reach, rural & sea views Portland, Dorset

England / Dorset / Isle of Portland / Portland

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Great for children of all ages ; Car not necessary;
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

from £120 / night

£900 - £1430 / week

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from £120 / night

1 / 8

Coral Cove Cottage - Portland cottage sleeps 5

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 57 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Suitable for children age 5+;
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 c  …see more

from £76 / night

£530 - £750 / week

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from £76 / night

(1) Good 

1 / 14

Artist Cottage - Portland cottage sleeps 4

England / Dorset / Isle of Portland / Portland

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Great for children of all ages ;
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 £68 / night

£475 - £675 / week

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from £68 / night

(1) Excellent 

1 / 10

Dory Cottage - Portland cottage sleeps 5

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Suitable for children age 5+;
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 £57 / night

£400 - £750 / week

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from £57 / night

(25) Very Good 

1 / 22

Rosa Cottage - Portland cottage sleeps 5

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.2 km; Great for children of all ages ;
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  …see more

from £75 / night

£320 - £720 / week

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from £75 / night

1 / 8

Sea View - Portland cottage sleeps 6

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Great for children of all ages ;
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 designed to slee  …see more

from £85 / night

£400 - £850 / week

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from £85 / night

(1) Excellent 

1 / 6

10 Fortuneswell - Portland cottage sleeps 4

England / Dorset / Isle of Portland / Portland

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Suitable for children age 5+;
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 £57 / night

£400 - £675 / week

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from £57 / night

(6) Excellent 

1 / 10

Chiswell Cottage - Portland cottage sleeps 8

England / Dorset / Isle of Portland / Portland

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Great for children of all ages ;
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  …see more

from £93 / night

£450 - £950 / week

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from £93 / night

1 / 14

Marina Bay View Apartment - Portland Harbour

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; 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 £95 / night

£1050 / week

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from £95 / night

(13) Very Good 

1 / 14

Bakers Dozen - Three Bedroom Coastal Cottage

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Great for children of all ages ; Car advised;
A charming three bedroomed character property, situated in a quiet location on the southern part of the Isle of Portland with panoramic sea views to the rear. Beautiful coastal paths and scenery close by, ideal for a chilled out relaxing break. The house has a televisi  …see more

from £95 / night

£595 - £750 / week

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from £95 / night

1 / 8

Mermaid Cottage - Portland house sleeps 10

England / Dorset / Isle of Portland / Portland

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Great for children of all ages ; Car advised;
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 to open  …see more

from £71 / night

£500 - £1000 / week

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from £71 / night

(4) Excellent 

1 / 17

1 The Old Police Station - Portland house sleeps 7

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 77 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Great for children of all ages ;
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 £93 / night

£650 - £900 / week

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from £93 / night

(6) Very Good 

1 / 22

Ocean Studio Apartments OSA11A-Southwell, Portland

England / Dorset / Isle of Portland / Portland

StudioSleeps 22 nights min stay

  • Studio
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 3 km; Suitable for children age 5+; Car advised;
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  …see more

from £49 / night

£300 / week

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from £49 / night

(2) Very Good 

1 / 18

1 Bow & Arrow Cottages - Portland house sleeps 8

England / Dorset / Isle of Portland / Portland

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.2 km; Suitable for children age 5+;
This elegantly refurbished 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 flo  …see more

from £100 / night

£700 - £1350 / week

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from £100 / night

(1) Very Good 

1 / 32

England / Dorset / Isle of Portland / Portland

StudioSleeps 23 nights min stay

  • Studio
  • Sleeps 2
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 11 km; Great for children of all ages ;
 …see more

from £45 / night

£315 / week

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from £45 / night

(1) Excellent 

1 / 17

Ocean Studio Apartments OSA12- Southwell, Portland

England / Dorset / Isle of Portland / Portland

StudioSleeps 32 nights min stay

  • Studio
  • Sleeps 3
  • 2 nights min stay
Key info: Suitable for children age 5+; Car essential; No pets allowed;
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  …see more

from £79 / night

£500 / week

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from £79 / night

(9) Very Good 

1 / 9

Pebble View - Portland house sleeps 6

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 64 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Great for children of all ages ;
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 floorsThe newly refurbished cottage arranged over three floors comprises of t  …see more

from £65 / night

£420 - £640 / week

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from £65 / night

(1) Very Good 

1 / 34

England / Dorset / Isle of Portland / Portland

StudioSleeps 22 nights min stay

  • Studio
  • Sleeps 2
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 11 km; Suitable for children age 5+;
 …see more

from £79 / night

£550 / week

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from £79 / night

(3) Excellent 

1 / 18

Windmills - Portland house sleeps 6

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Great for children of all ages ; Some pets are welcome - please contact the owner;
New 3 bedroom house located in a quite cul de sac in Easton on the Isle of Portland at the centre of the Jurassic coast two double bedrooms one twin 3 toilets secure storage for bikes etc. 2 private parking spaces. Ground floor consists of a hallway, a large utility ro  …see more

from £80 / night

£650 - £800 / week

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from £80 / night

1 / 14

England / Dorset / Isle of Portland / Portland

StudioSleeps 22 nights min stay

  • Studio
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 11 km; Ask owner if suitable for children; Car advised;
 …see more

from £59 / night

£350 - £399 / week

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from £59 / night

(1) Excellent 

1 / 28

Seagull House Portland Dorset - Portland house sleeps 7

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 77 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Great for children of all ages ;
Seagull House sits in prime position on the site used as the 2012 Olympic Sailing Village. The house, used by teams during the Olympics, is a large four storey house with direct views of the vast Chesil Beach & Atlantic Ocean beyond plus Portland Marina with it'  …see more

from £120 / night

£840 - £1200 / week

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from £120 / night

1 / 11

Casita del mar - Portland house sleeps 6

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 5 km; Great for children of all ages ;
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 £120 / night

£465 - £750 / week

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from £120 / night

1 / 10

High Street - Portland private room sleeps 5

England / Dorset / Isle of Portland / Portland

5 bedroomsSleeps 57 nights min stay

  • 5 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Not suitable for children; No pets allowed;
Well suited single occupancy rooms, possibly suitable for a couple with an additional fee providing access to communal living room, kitchen & utility room. On the ground floor there is communal living room, kitchen & one bedroom. On the first floor there are two bedro  …see more

from £20 / night

£140 / week

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from £20 / night

1 / 18

Holiday Home Weymouth and Portland - Portland house sleeps 6

England / Dorset / Isle of Portland / Portland

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Great for children of all ages ; Pets welcome; Private garden;
Brand new Town House in the attractive Easton part of Portland. The house is well equipped with distant sea views from the master bedroom. From the door you can go on several walks, climb, mountain bike, road cycle, sail, wind surf, dive, SUP and swim. Church Op Cove is  …see more

from £120 / night

£800 / week

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from £120 / night

(1) Excellent 

1 / 10

Frigate Apartment - Portland apartment sleeps 4

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Swimming pool;
Frigate Apartment is a stunning holiday apartment with sea views situated in the eyecatching Ocean Views development, close to Portland Harbour and the National Sailing Academy. Balcony, use of swimming pool, jacuzzi and fitness suite.There are two double bedrooms, each  …see more

from £93 / night

£650 - £900 / week

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from £93 / night

Top Destination reviews

Rosa Cottage
Wonderful holiday home

We stayed at Rosa Cottage for a week in March, and had a wonderful stay. The cottage is furnished to a high standard with a tasteful and original look. The kitchen is well equipped, and we had some wonderful evenings around the large dining room … see more
fishermans view
Fantastic Cottage

Spent a week at Fisherman's View with my wife and dog, my daughter joined us for a few days. The cottage is in an ideal spot to explore Portland, Weymouth and all surrounding coast. Fishermans View was spotlessly clean and very welcoming and comfor … see more
Quarries Reach, rural & sea views Portland, Dorset
Perfect for a short break with friends

Nice sized house, close to the sea and shops. Good shower and easy to find. Perfect amount of bathrooms for 6 people. Small but cozy living room area. Great stay! … see more
Church Ope Studio
Lovely homely place & great location

The studio has all the things you need for a short break, we took Ruby our West highland terrier and she loved it just as much as we did. The location is great and as you leave the studio to the left is the lane that leads to the coastal path an … see more

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