Air conditioned apartments and villas to rent in Trinidad and Tobago

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Trinidad and Tobago

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158 Holiday homes

Filters applied: Air conditioning

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

(8) Very Good 

15

Trinidad and Tobago holiday villa rental

Tobago / Scarborough

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 £220 / night

£1540 - £2212 / week

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from £220 / 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 - £1000 / week

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from £140 / night

(2) Excellent 

18

Condo letting in Trinidad and Tobago 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 £144 / night

£1008 / week

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from £144 / 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

(9) Very Good 

32

Holiday villa with swimming pool, golf nearby in Mount Irvine

Tobago / Mount Irvine

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Tranquility in Paradise” I have stayed at Eternity Villa on my last two trips to Tobago. I consider it home away from home. On both occasions I brought my family and the house was more than accomodating for everyone. Located in Mt Irvine and amazin  …see more

from £192 / night

£1280 - £2000 / week

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from £192 / night

5

Holiday apartment with swimming pool in Trinidad and Tobago

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 £40 / night

£560 - £840 / week

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from £40 / night

(21) Very Good 

27

Holiday villa with swimming pool, golf nearby in Trinidad and Tobago

Tobago / Prospect, Tobago

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 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 £200 / night

£1200 / week

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from £200 / night

(11) Very Good 

18

Holiday villa with swimming pool in Trinidad and Tobago

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

10

Villa rental in Trinidad and Tobago

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 £120 / night

£760 - £800 / week

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from £120 / 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

(1) Excellent 

23

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

(17) Excellent 

12

Holiday villa with swimming pool in Trinidad and Tobago

Tobago / Bon Accord

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“The best villa I've rented in Tobago” The villa is situated near to Crown Point and is located close to two of Tobago's best beaches. The villa is beautifully decorated and incredibly comfortable. It suited myself, my mum and my two children perfectly  …see more

from £148 / night

£1040 - £1440 / week

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from £148 / night

(1) Very Good 

22

Holiday apartment in Mayaro

Trinidad / Mayaro

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Car rental available from £45 per day  …see more

from £120 / night

£720 - £1056 / week

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from £120 / night

22

Holiday villa with swimming pool in Trinidad and Tobago

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 £208 / night

£1360 - £1720 / week

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from £208 / night

20

Holiday apartment in Trinidad and Tobago

Trinidad / Port of Spain

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 5 km
  • Child friendly
  • Car not necessary
Lovely Apartment, Perfect Location,Offers space and flexibility at affordable priceClean, comfortable  …see more

from £56 / night

£392 - £728 / week

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from £56 / night

4

Holiday apartment with swimming pool in Trinidad and Tobago

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 £80 / night

£560 - £840 / week

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from £80 / night

(13) 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 £320 / night

£2240 / week

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from £320 / night

(1) Excellent 

19

Mayaro holiday home rental

Trinidad / Mayaro

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Child friendly
Car rental available from $45 per day  …see more

from £120 / night

£720 - £1056 / week

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from £120 / night

17

Caroni holiday apartment rental

Trinidad / Caroni

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Welcome to our largest apartment. This five(5) bedroom, 2 bathroom beauty is the perfect apartment for a larger family coming on vacation. It can host up to 10 persons. 1200 sq ft of living space is more than enough for a comfortable short stay. ADDITIONAL SERVICES (  …see more

from £160 / night

£1120 / week

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from £160 / night

(14) 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 £80 / night

£560 - £840 / week

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from £80 / night

10

Holiday apartment in Caroni

Trinidad / Caroni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Spacious 2 bedroom apartment, located in the breezy, serene plains of east/central Trinidad. Only 10 minutes to the airport, to 4 major shopping malls, educational district of universities and colleges, famous Caroni Bird Sanctuary and other attractions. There is also a  …see more

from £80 / night

£560 / week

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from £80 / night

10

Trinidad and Tobago holiday studio rental

Trinidad / Woodbrook

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 14 km
  • Car not necessary
  • Air conditioning
Well-appointed, self-catering private exterior apartment separate from main house. Easy access to downtown, shopping, beaches, tourist sites. Prime location for annual Carnival celebrations. Laundry and parking available on premises for additional fee. Airport runs av  …see more

from £44 / night

£276 / week

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from £44 / night

(1) Excellent 

24

Villa letting in Trinidad and Tobago 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 £280 / night

£1960 - £2240 / week

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from £280 / 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 

16

Caroni holiday apartment rental

Trinidad / Caroni

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Spacious 2 bed apt, located in the breezy, serene plains of east/central Trinidad. Only 15 tothe airport, to 4 major shopping malls, educational district of universities and colleges, famous Caroni bird sanctuary and other attractions. 700sq ft. ADDITIONAL SERVICES (Su  …see more

from £80 / night

£560 / week

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from £80 / night

19

Holiday apartment in Caroni

Trinidad / Caroni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Spacious 2 bedroom apartment, located in the breezy, serene plains of east/central Trinidad. Only 10 minutes to the airport, to 4 major shopping malls, educational district of universities and colleges, famous Caroni Bird Sanctuary and other attractions. There is also a  …see more

from £80 / night

£560 / week

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from £80 / 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 £80 / night

£560 - £840 / week

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from £80 / night

(1) Excellent 

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
  • Swimming pool
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 £440 / night

£3080 / week

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from £440 / night

13

Woodbrook holiday studio rental

Trinidad / Woodbrook

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • Car not necessary
  • Air conditioning
10% discount for 7-day stays, 30% discount for monthly stays. No discounts during Carnival season.  …see more

from £36 / night

£224 - £280 / week

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from £36 / 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

(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

(2) Very Good 

19

Holiday villa with swimming pool, golf nearby in Trinidad and 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
•A 22-metre pool, air conditioned wine cellar,manicured 2-acre garden, soft garden lighting, large verandah, equipped with hammock, swing seat and a wide range of loungers, chairs and tables, Bose stereo system throughout ground floor, verandah and pool area,<b  …see more

from £926 / night

£6480 / week

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from £926 / night

5

Holiday private room in Trinidad and Tobago

Trinidad / Caroni

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
This listing is perfect for 2 people in Transit. We offer airport transfers at a very small surcharge. You can't go wrong because this listing has hot and cold shower, all toiletries and basic amenities like toilet paper, shower curtain, bed linens, blankets, soap,  …see more

from £40 / night

£280 / week

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from £40 / night

(2) Average 

4

Holiday apartment with swimming pool in Trinidad and Tobago

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 £80 / night

£560 - £840 / week

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from £80 / night

8

Woodbrook holiday studio rental

Trinidad / Woodbrook

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 14 km
  • Car not necessary
  • Air conditioning
Well-appointed, self-catering private exterior apartment separate from main house. Easy access to downtown, shopping, beaches, tourist sites. Prime location for annual Carnival celebrations. Laundry and on-site parking available on premises for additional fee. Airport  …see more

from £36 / night

£228 / week

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from £36 / night

52

Caroni holiday home rental

Trinidad / Caroni

5 3 1 night min

  • 5 bedrooms
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Hostal Groning is located in the beautiful city of Trinidad , the third village founded in Cuba by Diego Velázquez in 1514. In 1988 , UNESCO inscribed in the World Heritage List the Old Town and the “Valle de los Ingenios” . This small town, located i  …see more

from £26 / night

£153 / week

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from £26 / night

(1) Average 

20

Trinidad / Caroni

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £30 / night

£208 / week

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from £30 / night

7

Holiday home in Trinidad and Tobago

Trinidad / Port of Spain

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Air conditioning
no thing to say, Travellers look for specific criteria when searching for a home, so take the time to fill out as many details here as you canTravellers look for specific criteria when searching for a home, so take the time to fill out as many details here as you canTra  …see more

from £235 / night

£1645 / week

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from £235 / night

(3) Very Good 

25

Trinidad / Chaguanas

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 40 km
  • Air conditioning

 …see more

from £56 / night

£415 - £624 / week

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from £56 / night

(1) Excellent 

4

Port of Spain / St. Ann's

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning

 …see more

from £56 / night

£352 / week

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from £56 / night