50 Best Vacation Rentals in Calheta - Holiday Lettings - Cabins

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Arco da Calheta
186 properties
Estreito da Calheta
52 properties
Prazeres
41 properties
Ponta do Pargo
31 properties
Faja da Ovelha
28 properties
Paul do Mar
23 properties
Jardim do Mar
10 properties

Calheta

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1,527 Vacation rentals

(31) Excellent 

48

Vacation villa in Calheta

Madeira / Calheta

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
This magnificent luxury villa has breath-taking views of the glistening Atlantic Ocean and overlooks the cosmopolitan village, marina and sandy beaches of Calheta, just 1km away. Located right on the cliff top, with a spectacular heated infinity pool, it is finished to …see more

from $277 / night

$1,761 - $3,244 / week

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avg. 3 hours 42 minutes

from $277 / night

(2) Very Good 

18

Vacation villa in Estreito da Calheta

Calheta / Estreito da Calheta

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in the sun-drenched hills above Calheta, an old barn has been transformed into this new contemporary modern and chic 3-bed air-conditioned villa, with everything you may want for a great family holiday. Built to high standards, and very well furnished in a modern st …see more

from $118 / night

$825 / week

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Responds fast!
avg. 1 hour 16 minutes

from $118 / night

(1) Excellent 

26

Vacation cottage in Arco da Calheta

Calheta / Arco da Calheta

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 10 mi
  • Private garden
Small Lodge made of recycled wooden pallets over a water tank. Very cozy, with lots of green surroundings, mountain view, and outside walls also made with recycled materials. Unique in Madeira. The house is on the north side of a small estate in Calheta. Has lots of s …see more

from $71 / night

$483 / week

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from $71 / night

22

Vacation cottage with golf nearby in Arco da Calheta

Calheta / Arco da Calheta

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
This is a beautiful traditional farm Madeira Cottage. The area is very private and very quiet. The rustical cottage built with nature stones was built in the typical madeiran farmhouse style with a cosy and comfortable atmosphere. The house is near to a small road o …see more

from $69 / night

$478 / week

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from $69 / night

11

Faja da Ovelha Vacation home rental

Calheta / Faja da Ovelha

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 9 mi
  • Child friendly
  • Pet friendly
Raposeira Chloe is a typical house from Madeira built recently, in a country setting, quiet and cozy own to rest and feel nature. It is prepared for all types of guests: the nature lovers can hike or walk on trails that are taken at the place. Your preference is the mo …see more

from $45 / night

$313 / week

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from $45 / night

(2) Excellent 

25

Calheta Vacation villa rental

Madeira / Calheta

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Don't be fooled by the photos. This villa is even more charming than it looks! A high class build with a location that is postcard perfect! The villa is part of small suburban development that has all the modern amenities of a top class neighborhood! This house is fo …see more

from $200 / night

$1,400 / week

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from $200 / night

24

Home rental in Prazeres

Calheta / Prazeres

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
Excellent house for holidays near the beach and the mountain. It has 1 living room with fireplace, 2 double bedrooms, 1 bedroom with a single + extra bed bed, 2 bathrooms, 1 kitchen, 1 outdoor barbecue, 1 large terrace overlooking the sea and mountain and covered space …see more

from $48 / night

$330 / week

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from $48 / night

14

Home rental in Estreito da Calheta with golf nearby

Calheta / Estreito da Calheta

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
1 bedroom and a sofa bed to sleep 3 in a quiet place, in Madeira... - Full kitchen - 2 bathrooms - Very quiet, - Isolate paradise - Barbecue - Sun chairs - Patio chairs and table - Near to Hotel Jardim Atlantico - WI-FI internet free Travel: airport at 35 minut …see more

from $65 / night

$453 / week

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from $65 / night

(8) Excellent 

Certificate of Excellence

19

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Panoramica, 4 bedrooms,large swimming pool ,with unbelievable seaview A 4 bedroom luxury villa located in Arco da Calheta. the property has 4 luxury modern style bedrooms, 3 luxurious modern bathrooms and an open-garden bathroom with shower new modern kitchen, lau …see more

Certificate of Excellence

from $153 / night

$1,071 - $1,400 / week

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from $153 / night

(1) Excellent 

20

Estreito da Calheta Vacation home rental

Calheta / Estreito da Calheta

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bedrooms, 3 bathrooms, separate WC, sleeps 8 Casa Frangipani is an outstanding modern villa standing on a large level site in the hamlet of Estreito da Calheta on the south-west coast of the beautiful sub-tropical island of Madeira. Designed in a contemporary style b …see more

from $250 / night

$1,752 / week

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from $250 / night

45

Vacation home in Calheta

Madeira / Calheta

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Private garden
"Laurishouse" is a house with 2 bedrooms, near the Nature, in Prazeres, with CERTIFIED PERMIT / LICENSE LOCATION ACCOMMODATION No 4/12 of 2012/04/03 located in Prazeres, Calheta-Madeira, with a space green landscaped with about 250m2 with flowers, fruit trees, herbs, et …see more

from $42 / night

$289 / week

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Responds fast!
avg. 2 hours 6 minutes

from $42 / night

(3) Excellent 

20

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

2 3 5 nights min

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min
  • Nearest beach 2 mi
  • Private garden
Very peace located modern apartment with 2 bedrooms; one with a double bed and other with a single bed - possibility to have an extra single bed. The area of the garden is nice and flowes and planted exotic plants. Was built in the year 2000, the accommodation on the gr …see more

from $62 / night

$429 / week

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from $62 / night

24

Vacation apartment in Arco da Calheta

Calheta / Arco da Calheta

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Child friendly
Somos um casal de 60 anos que decidimos compartir a parte de cima da nossa casa com pessoas gostam da ilha da madeira, o apartamento fica completamente independente da nossa casa, só tem em comum o portão principal. A área possui um bom acesso ao mar, e a beleza natura …see more

from $42 / night

$289 / week

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Responds fast!
avg. 3 hours 54 minutes

from $42 / night

34

Vacation villa in Arco da Calheta

Calheta / Arco da Calheta

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Private garden
The Villa Pure View is located on a hillside on the sunny South West coast, which is spoilt not only for its locations and views, but its climate too. This accommodation is perfect for guests who want to relax and enjoy the peace, tranquility and fabulous sea views that …see more

from $87 / night

$610 / week

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from $87 / night

25

Vacation home rental

Calheta / Prazeres

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Casa Da Levadinha is a place where guests will find peace and tranquillity with panoramic views of the Atlantic Ocean and the mountainous landscape of Madeira. It is located 30 km from Funchal. This house includes 2 double bedrooms and a spacious living room with sofas …see more

from $94 / night

$659 / week

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from $94 / night

(10) Excellent 

24

Vacation home in Estreito da Calheta

Calheta / Estreito da Calheta

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Gulf Stream waters lap the shores of Madeira resulting in fantastic summers and mild winters making the island an exquisite holiday destination all year round. Our spacious cottages enjoy a privileged location in Estreito da Calheta which is to be found on the sunny wes …see more

from $89 / night

$618 / week

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from $89 / night

(10) Excellent 

26

Estrela, Madeira Vacation apartment accommodation

Calheta / Estrela, Madeira

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 2 mi
  • Swimming pool
The property is located in one of the most sunny Madeira, Calheta. The apartment is all very well equipped in order to provide a memorable vacation, in a quiet area, and consists of: A bedroom with double bed, spacious, safe, and a bathroom right next to the same. The b …see more

from $83 / night

$577 / week

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from $83 / night

(12) Very Good 

Certificate of Excellence

38

Estreito da Calheta Vacation villa rental

Calheta / Estreito da Calheta

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Villa Murphy is situated in a typical rural area of Madeira. Panoramic sea views are simply breathtaking. The Villa offers two bedrooms; both bedrooms are large rooms with frenchdoors leading onto the top balcony. The views are spectacular. The balcony is large and spac …see more

Certificate of Excellence

from $83 / night

$581 - $936 / week

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Responds fast!
avg. 2 hours 44 minutes

from $83 / night

20

Home rental in Calheta

Madeira / Calheta

2 3 5 nights min

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Cottage rustic style used for vacation, located 2 km from the sea, a quiet area overlooking the sea and the mountain. House inside a sunny disposition throughout the day with a great outdoor space to enjoy sunny afternoons, which includes even a BBQ. WI-fi included. Su …see more

from $48 / night

$472 - $566 / week

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Responds fast!
avg. 1 hour 57 minutes

from $48 / night

19

Vacation home in Estreito da Calheta

Calheta / Estreito da Calheta

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Pet friendly
The house is equipped with everything needed to enjoy a great stay in Madeira, is near the main sights of Calheta, the taken of the island, walks in nature, and above all agree with the stunning sound of Nature here one breathes the fresh air and offers security and pea …see more

from $42 / night

$330 - $694 / week

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from $42 / night

(2) Excellent 

18

Vacation apartment in Faja da Ovelha

Calheta / Faja da Ovelha

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
Brand new building, built with your comfort in mind, this economic and cozy studio apartment located in Fajã da Ovelha provides a magnificent view of the Atlantic Ocean as well as the sunset. Ideal retreat for a couples vacation on the Island of Madeira, isolated from t …see more

from $36 / night

$248 / week

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Responds fast!
avg. 20 minutes

from $36 / night

21

Vacation cottage in Arco da Calheta

Calheta / Arco da Calheta

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
This beautiful stone property was restored in 2009, in a peaceful rural location in Atouguia, a small parish within Calheta, with lovely views of the ocean and mountains. There are 2 bedrooms, 2 toilets, lounge and kitchen with all appliances. It have open fire and air …see more

from $62 / night

$429 - $593 / week

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Responds fast!
avg. 11 minutes

from $62 / night

(1) Excellent 

12

Vacation home in Faja da Ovelha

Calheta / Faja da Ovelha

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
This property has breathtaking views over the ocean and enjoys a really nice sun exposure throughout the year. Madeira has a mild climate so it's never gonna be too hot or too cold. Even in winter. Which makes it an interesting destination all year round. From th …see more

from $94 / night

$588 - $765 / week

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Responds fast!
avg. 2 hours 43 minutes

from $94 / night

(2) Excellent 

24

Arco da Calheta Vacation home rental

Calheta / Arco da Calheta

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Pink house is situated between Arco da Calheta and Loreto with a fantastic view over Arco da Calheta. The house has been nicely decorated inside,and outside with a big an relaxing terrace with nice view above the ocean. The house has 2 bedroom,one with a double be …see more

from $53 / night

$372 / week

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from $53 / night

(6) Very Good 

29

Prazeres Vacation home rental

Calheta / Prazeres

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 4 mi
  • Child friendly
  • Ask about pets
2 to 4 guests. Area of 55 m 2 full foot. Room 1: reads Double + convenient. 1 bathroom: Italian shower + washbasin + WC. 1 kitchen open to living room: kitchen: hotplate x 4 + oven + hood hood + fridge / freezer + microwave oven + coffee Italian + Grill bread Table and …see more

from $67 / night

$470 - $552 / week

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from $67 / night

(2) Excellent 

20

Vacation villa with swimming pool in Arco da Calheta

Calheta / Arco da Calheta

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
The village of field with high quality pool atop a seaside cliff. Stunning views of the Atlantic Ocean, to the South coast of Madeira Island and the green banana plantations. Intimate, bucolic, peaceful and relaxing. Ideal for holidays and rest. The only noise is the wa …see more

from $200 / night

$1,400 - $3,129 / week

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from $200 / night

(2) Very Good 

26

Vacation villa in Prazeres

Calheta / Prazeres

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Purposely designed for holiday rentals to include the most sought after features, and located on the rolling hills below Prazeres, the air-conditioned 5-bedroom Eden Nature Villa has outstanding panoramic views over the green countryside to the sea and coast, an inside/ …see more

from $130 / night

$906 / week

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Responds fast!
avg. 1 hour 15 minutes

from $130 / night

(4) Excellent 

18

Vacation home rental

Calheta / Estreito da Calheta

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Gulf Stream waters lap the shores of Madeira resulting in fantastic summers and mild winters making the island an exquisite holiday destination all year round. Our spacious cottages enjoy a privileged location in Estreito da Calheta which is to be found on the sunny wes …see more

from $112 / night

$783 / week

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from $112 / night

(3) Excellent 

12

Vacation home in Estreito da Calheta

Calheta / Estreito da Calheta

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Beautifull and recently renovated stone house with two bedrooms both with sea view, one bathroom,fully equipped kitchen,garden area,BQ area,car park ,5 minutes from the yellow sand beach and with an excellent sun exposure. Supermarket and bar within a walking distance,s …see more

from $71 / night

$494 / week

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from $71 / night

(1) Excellent 

14

Vacation cottage rental

Calheta / Arco da Calheta

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Ask about pets
The House is near the beach 5 minutes drive near banking, hospital pharmacies all around is in the countryside very quiet location with a spectacular view has everything Chair for living in comfort has in cooking appliances required tv with international channels INTERN …see more

from $83 / night

$577 - $618 / week

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from $83 / night

(5) Excellent 

18

Vacation home with swimming pool in Arco da Calheta

Calheta / Arco da Calheta

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxurious village located near everything you need. Amazing sunset view just for who love nature. House of two floors with 5 bedrooms, 5 bathrooms, a living room and dining r / c open space. Garden overlooking the sea, terrace overlooking the sea and mountains, barb …see more

from $223 / night

$1,550 / week

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from $223 / night

(2) Excellent 

27

Ponta do Pargo Vacation home rental

Calheta / Ponta do Pargo

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
Villa Montemar is the perfect spot to recharge energies and find peace among the comfort of a home away from home. It is a 2 bedroom house prepared to receive 4 people. The Kitchen is fully equipped... You will certainly find everything you need for a perfect stay. Vill …see more

from $53 / night

$371 - $577 / week

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Responds fast!
avg. 3 hours 45 minutes

from $53 / night

(26) Very Good 

Certificate of Excellence

33

Home rental in Estreito da Calheta

Calheta / Estreito da Calheta

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
This old stable is beautifully refurbished and has a cool patio under the vines. The area around is mainly farmed and perfect if you would like to stay close to the beach. The house consist of 2 bedrooms upstairs (both with double beds). Downstairs you have the sittin …see more

Certificate of Excellence

from $42 / night

$289 / week

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Responds fast!
avg. 2 hours 30 minutes

from $42 / night

(2) Excellent 

27

Arco da Calheta Vacation apartment rental

Calheta / Arco da Calheta

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A & M House: it is a fantastic place where you can relax in your well-deserved family vacation. The house consists of two bedrooms, one with double bed "king size", the second bedroom has two single beds and can join and make a double bed. the rooms have air conditionin …see more

from $130 / night

$906 / week

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Responds fast!
avg. 38 minutes

from $130 / night

(16) Excellent 

Certificate of Excellence

44

Beach hut rental in Jardim do Mar with swimming pool

Calheta / Jardim do Mar

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
'HOUSE WHERE THE MOUTINES MEET THE SEA "(New - Summer spaces are available) The villa, is called the" house where the mountain meets the sea "due to, in one house, can enjoy simultaneously sea ​​and rustic mountain nature, that because the 1st floor is the pool area and …see more

Certificate of Excellence

from $100 / night

$700 / week

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Responds fast!
avg. 2 hours 44 minutes

from $100 / night

(1) Very Good 

45

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Private garden
It sits on the hillside overlooking the beautiful Bow village of Calheta in SW Madeira. This piece of coast, known as the 'Costa Verde' has some of the most beautiful views of Madeira and as such is fast becoming the place to live and holiday for the discerning. The hou …see more

from $71 / night

$494 - $1,417 / week

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Responds fast!
avg. 3 hours 54 minutes

from $71 / night

(1) Excellent 

53

Vacation home in Estreito da Calheta

Calheta / Estreito da Calheta

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Relax in Class at 200m high on the Sunny South West Coast of Madeira and enjoy the Sunset and Ocean View from the Pool! You can rent Casa Palheiro - studio, Casa Rural - 1 bedroom, Casa Eco - 2 bedrooms, or any combination. Have a look on the Picture Galleries to make s …see more

from $100 / night

$665 - $779 / week

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from $100 / night

29

Villa rental in Calheta

Madeira / Calheta

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Child friendly
  • Private garden
A beautiful fully equipped & licensed by Madeira authorities holiday home, built in 2013 and located in an attractive village of Arco da Calheta, situated in the south west of the island. This holiday villa is stylishly furnished and decorated to a high standard. Absolu …see more

from $59 / night

$412 - $577 / week

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Responds fast!
avg. 11 minutes

from $59 / night

(12) Very Good 

23

Vacation home in Paul do Mar

Calheta / Paul do Mar

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
Harbour House looks out across the Atlantic ocean and the harbour at Paul do Mar where fishing vessels land their catches daily, retaining the charm of a traditional Madeiran fishing village. A small holiday house with breathtaking views of the sea, on all three flo …see more

from $71 / night

$495 / week

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Responds fast!
avg. 27 minutes

from $71 / night

24

Prazeres Vacation villa rental

Calheta / Prazeres

4 7 1 night min

  • 4 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Pet friendly
ALL INCLUSIVE PACKAGE! Vacation Rental + Rent-a-Car Included. The best price guaranteed. For more information, please send me a message. The area is very peaceful and is perfect for those guests wishing to get away from it all. The guests have full access to the pro …see more

from $295 / night

$2,061 / week

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from $295 / night