Villas in Tobago and houses – Holiday Lettings - Holiday Rentals Tobago

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North America Holidays
169262 properties
Caribbean Holidays
28708 properties
Villas Castara
28 properties
Crown Point
14 properties
Scarborough
10 properties
Apartments Bon Accord
9 properties
Buccoo
9 properties
Mount Irvine
8 properties
Lowlands
6 properties
Arnos Vale
6 properties
Estates Black Rock
5 properties

Tobago

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129 Holiday homes

Travellers going to Tobago are booking February dates now. Secure your holiday home today and have the perfect trip.

(18) Excellent 

20

Castara holiday villa rental

Castara / Englishman's Bay

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Very peaceful and spacious home in a great location.” Everything was well prepared when we arrived. Jango (the master gardener and our greeter when we arrived) was very patient and waited for 4 hours as our flight was delayed. The house was well equi  …see more

from £114 / night

£800 - £1450 / week

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from £114 / night

(10) Excellent 

18

Holiday villa with swimming pool in Mount Irvine

Tobago / Mount Irvine

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Mot Mot Lodge has an open plan living, dining and kitchen area, with double hight ceilings and full width sliding doors, opening out on to a large upper patio,with outdoor dining facilities. This dining area links the interior and the garden seamlessly.  …see more

from £230 / night

£1610 / week

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from £230 / night

(20) Very Good 

28

Holiday villa with swimming pool, golf nearby in Prospect, Tobago

Tobago / Prospect, Tobago

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“A fabulous relaxing holiday in a spectacular part of the world.” Villa in fabulous elevated private location, with fantastic views out over the Atlantic Coast line during the day time, and constantly changing night time views of the low lands. The vi  …see more

from £195 / night

£1400 / week

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from £195 / night

(2) Excellent 

18

Condo letting in Lowlands with shared pool, golf nearby

Tobago / Lowlands

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly
It's a ground floor condo overlooking the Tobago Plantations golf course. tranquil and peaceful surroundings. Access to 3 separate pools on compound and Lowlands beach. Sleeps 8 comfortably. Perfect for small families with young children. Cable television and wifi  …see more

from £148 / night

£1033 / week

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from £148 / night

(12) Excellent 

12

Holiday villa in Buccoo

Tobago / Buccoo

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
From $400 US per night.Oleander Villa Stunning views over Pigeon Point/Buccoo Reef near Mt.Irvine golf course  …see more

from £328 / night

£2296 / week

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from £328 / night

(15) Very Good 

21

Bacolet Bay holiday villa rental

Tobago / Bacolet Bay

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
Luxury villa with swimming pool just 5 minutes from the beach. Ideal for family holidays, couples getting away for a break, honeymooners or friends wanting a good time.  …see more

from £140 / night

£850 / week

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from £140 / night

(17) Excellent 

12

Holiday villa with swimming pool in Bon Accord

Tobago / Bon Accord

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Just what we needed” Superb location within walking distance of great beach. Also close to airport - we were in the villa within 40 minutes of landing. The villa is in a good residential area and security is excellent. It has everything you need fo  …see more

from £152 / night

£1066 - £1476 / week

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from £152 / night

9

Holiday apartment rental

Tobago / Black Rock

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Air conditioning
Cozy and romantic one bedroom villa with a wounderful view of the Buccoo Reef sea, from the sun porch and private jacuzzi. It is ideally suited for honeymoons, anniversaries and short to long term breaks.<br />Jucuzzi, air conditing, large outside balcony, gas BBQ  …see more

from £80 / night

£500 - £600 / week

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from £80 / night

22

Holiday villa with swimming pool in Bon Accord

Tobago / Bon Accord

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.7 km
  • Swimming pool
Tropical Luxury is located in the beautiful caribbean island of Tobago. Boasting 4 bedrooms, 3 toilet/baths, fully air-conditioned, private pool and jacuzzi, 40" HD LED TV with premium cable, High speed wifi, comfortably accommodating ten persons. On the ground fl  …see more

from £226 / night

£1476 - £1763 / week

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from £226 / night

(1) Excellent 

24

Villa letting in Mount Irvine with swimming pool, golf nearby

Tobago / Mount Irvine

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Swimming pool
This superb mexican style villa on 3 levels has stunning views over the palm trees to the Golf Course, Pigeon Point, Nylon Pool, Buccoo Reef and the Caribbean Sea. One of just four private villas set in a secluded cul-de-sac above the Mt. Irvine Golf Course it has a l  …see more

from £287 / night

£2009 - £2296 / week

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from £287 / night

(12) Very Good 

16

Holiday apartment with swimming pool in Castara

Tobago / Castara

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Situated next to Heavenly Bay (the smaller of Castara's two beaches), our apartments offer you an escape to paradise. Angel Retreat has eight apartments - each apartment has a two queen size beds with mosquito net, fitted air-conditioning, a large bathroom (with sh  …see more

from £82 / night

£574 - £861 / week

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from £82 / night

5

Holiday apartment with swimming pool in Castara

Tobago / Castara

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Situated next to Heavenly Bay (the smaller of Castara's two beaches), our apartments offer you an escape to paradise. Angel Retreat has eight apartments - each apartment has a two queen size beds with mosquito net, fitted air-conditioning, a large bathroom (with sh  …see more

from £41 / night

£574 - £861 / week

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from £41 / night

(8) Very Good 

15

Scarborough holiday villa rental

Tobago / Scarborough

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
Large living areas with unique wooden furnishings are spacious, airy and command a view of the patio which open on to the jacuzzi and large swimming pool over looking the 12th fairway of the golf course.GROUND REP & HOUSEKEEPER AWAIT YOU.  …see more

from £226 / night

£1578 - £2267 / week

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from £226 / night

10

Villa rental in Buccoo

Tobago / Buccoo

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 0.2 km
  • Child friendly
  • Car not necessary
Ocean View villa is a two story 3000 square foot charming villa located at the end of a quiet street overlooking the Caribbean sea.The ground floor is built on the open area concept and has a kitchen complete with fridge,stove,toaster,microwave, coffee maker,cutlery and  …see more

from £123 / night

£779 - £820 / week

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from £123 / night

(1) Excellent 

6

Villa rental in Black Rock with swimming pool

Tobago / Black Rock

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
RIDGE HOUSE VILLA SITS ON HORSE SHOE RIDGE ABOVE THE VILLAGE OF PLEASANT PROSPECT,WHICH HAS A RESTAURANT,BAR,AND SMALL SUPERMARKET. A SHORT WALK TO THE PALM TREE LINED SANDY BEACH WHERE LEATHERBACK TURTLES COME TO LAY THERE EGGS. IT ALSO HAS A BAR FOR FOOD AND DRINK,B  …see more

from £380 / night

£2660 / week

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from £380 / night

(1) Excellent 

6

Holiday apartment rental

Tobago / Castara

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Large air-conditioned apartment set in beautiful Heavenly Bay, 30 seconds to beach. Stunning sea views overlooking the Caribbean sea. Private swimming pool. Living close to nature. Unspoiled, unhurried, complete antidote to modern living. Fresh fish from local fisherman  …see more

from £82 / night

£574 - £861 / week

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from £82 / night

4

Holiday apartment with swimming pool in Castara

Tobago / Castara

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Situated next to Heavenly Bay (the smaller of Castara's two beaches), our apartments offer you an escape to paradise. Angel Retreat has eight apartments - each apartment has a two queen size beds with mosquito net, fitted air-conditioning, a large bathroom (with sh  …see more

from £82 / night

£574 - £861 / week

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from £82 / night

(1) Average 

23

Villa rental in Scarborough with swimming pool

Tobago / Scarborough

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Moonlight Mountain is built along traditional lines, it is what is called in the Caribbean a gingerbread house - a reference to the decorative fretwork which adorns the outside. Set in what used to be agricultural land and designed to catch the sea breezes, it has its o  …see more

from £155 / night

£1085 / week

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from £155 / night

(1) Very Good 

5

Holiday apartment in Castara

Tobago / Castara

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
Sea views  …see more

from £72 / night

£504 / week

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from £72 / night

17

Holiday home in Scarborough

Tobago / Scarborough

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 5 km
  • Child friendly
  • Air conditioning
The Bougainville Guest-House is located in a quiet breezy cul-de-sac with open views. The property is fenced, gated and is centrally located between the main town, scarborough and some of the most popular beaches on the Island. There are also a number of restaurants  …see more

from £105 / night

£735 / week

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from £105 / night

(1) Excellent 

15

Holiday villa with shared pool, golf nearby in Mount Irvine

Tobago / Mount Irvine

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly
Mahogany Villa is located at Mount Irvine in 2.5 acres of landscaped tropical gardens shared with just four other villas. With lovely views across the award winning golf course and through palm trees to the Caribbean Sea, guests at Mahogany will enjoy the peaceful, secl  …see more

from £230 / night

£1610 / week

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from £230 / night

(3) Excellent 

13

Apartment rental in Black Rock with shared pool

Tobago / Black Rock

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
With fantastic uninterrupted Caribbean sea views, Chaconia is an extremely well furnished, upscale apartment offering immediate access to one of the top beaches on the Island. While sitting on your patio and listening to the sound of the waves, you can enjoy having brea  …see more

from £233 / night

£1600 - £1750 / week

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from £233 / night

(2) Excellent 

7

Holiday apartment rental

Tobago / Castara

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Ask owner if suitable for children
Traditionally built wood over block long house overlooking the village, beaches and bay of Castara below . All rooms open out onto a private balcony / veranda with wide views of the sea and sunsets surrounded by forest, flowering plants, fruit trees and birds galore!&  …see more

from £115 / night

£805 / week

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from £115 / night

18

Holiday villa accommodation

Tobago / Goodwood, Tobago

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Beautiful surroundings, your own private pool, Tobago's best beaches only minutes away. Why would you choose anywhere else?  …see more

from £230 / night

£1560 / week

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from £230 / night

18

Holiday apartment in Castara

Tobago / Castara

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
5 rooms with a double bed for 50usd/night.3 rooms with two sets of bunks(1.40 m wide) for 60usd/night  …see more

from £54 / night

£357 / week

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from £54 / night

(19) Excellent 

24

Holiday home with swimming pool in Scarborough

Tobago / Scarborough

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
“An ideal family getaway that isn't far away” Spacious yet cozy, a place where you can be noisy without disturbing the peace or find a secluded spot whilst everyone else is partying. We had a large group and everyone was comfortably accommodated. The l  …see more

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9

Holiday apartment rental

Tobago / Castara

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
Sandcastles is located just above the small fishing village of Castara. The property overlooks the Caribbean sea and offers a 2-bedroom self-contained apartment with balcony, private gardens and kitchen.Fishing,rainforest and island tours organised.inhouse dining.  …see more

from £123 / night

£861 / week

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from £123 / night

12

Castara holiday apartment rental

Tobago / Castara

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
  • Private garden
Castara Cottage is a bright, airy and charming traditional wooden house located on a headland only two minutes walk away Castara's two beautiful white sand beaches. The house is divided into three spacious and well-equipped apartments that offer a variety of accom  …see more

from £58 / night

£402 / week

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from £58 / night

(1) Excellent 

4

Holiday apartment with swimming pool in Castara

Tobago / Castara

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Situated next to Heavenly Bay (the smaller of Castara's two beaches), our apartments offer you an escape to paradise. Our apartment Raster Man is on our 2nd floor. Locals and tourists share the restaurants, cafes and bars, and there are many shops in the village se  …see more

from £82 / night

£574 - £861 / week

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from £82 / night

16

Tobago / Goodwood, Tobago

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Private garden

 …see more

from £97 / night

£658 / week

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from £97 / night

(1) Excellent 

5

Castara holiday apartment rental

Tobago / Castara

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Beach / lakeside relaxation
  • Child friendly
Sea views, sunsets & bird watching Only a short walk from 2 beautiful beaches The main beach has life guards, the other quieter Little or Heavenly bay is especially good for snorkelling <br />For more pictures of the house, Castara & Tobago please see the  …see more

from £72 / night

£504 / week

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from £72 / night

(1) Excellent 

19

Holiday villa with swimming pool, golf nearby in Prospect, Tobago

Tobago / Prospect, Tobago

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Villa Petrus is a luxury Caribbean villa in Tobago, built in the plantation style, with outstanding facilities that accommodate up to 14 with ease, set in beautiful 2-acre grounds that include a 22 metre pool. Villa Petrus provides a luxurious serviced venue for family  …see more

from £949 / night

£6639 / week

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from £949 / night

12

Holiday villa rental

Tobago / Black Rock

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
Beachfront location of our property puts our pool, office and Beach Bar steps away from the spectacular golden sands of Stonehaven Bay, the 6 luxurious 3 bedroom villas are perched on a gentle hillside reaching down to the beach. Ideal for weddings or family reunions.&l  …see more

from £451 / night

£3156 / week

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from £451 / night

5

Castara holiday apartment rental

Tobago / Castara

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Car not necessary
"Our Place" is the 2 bedroomed self catering apartment upstairs at Carpe Diem Villa It consisting of the Green room (which can be taken separately) & the Yellow room. Both bedrooms have large ensuite bathrooms & are located at each end of the 48ft x 1  …see more

from £190 / night

£1330 / week

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from £190 / night

(13) Excellent 

7

Tobago / Charlotteville

5 8 3 nights min

  • 5 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £246 / night

£1640 - £1783 / week

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from £246 / night

(5) Very Good 

19

Tobago / Lambeau

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £246 / night

£1722 - £2296 / week

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from £246 / night

(2) Very Good 

18

Tobago / Crown Point

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £132 / night

£787 - £979 / week

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from £132 / night

(2) Very Good 

19

Tobago / Crown Point

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from £82 / night

£492 - £586 / week

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from £82 / night

(4) Excellent 

26

Tobago / Lowlands

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.48 km
  • Swimming pool

 …see more

from £226 / night

£1578 - £2267 / week

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from £226 / night

(3) Very Good 

11

Tobago / Bon Accord

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool

 …see more

from £304 / night

£2009 - £2582 / week

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from £304 / night

Top Destination reviews

The Fort Cottage
Lovely comfortabel historic cottage!!

Great cottage. Wonderful garden, great views over the bay and the city, wonderfully helpful owners. Everything you need is available at the Cottage. Location is great too, close to both sides of the island and to Scarborough and all the shops. If you … see more