50 Best Vacation Rentals in Calheta - Holiday Lettings - Cabins

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Arco da Calheta
196 properties
Estreito da Calheta
53 properties
Prazeres
37 properties
Ponta do Pargo
32 properties
Faja da Ovelha
31 properties
Paul do Mar
24 properties
Jardim do Mar
10 properties

Calheta

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1,556 Vacation rentals

(32) 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 $267 / night

$1,695 - $3,123 / week

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avg. 3 hours 7 minutes

from $267 / night

(5) Very Good 

24

Vacation villa with shared pool in Estreito da Calheta

Calheta / Estreito da Calheta

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly
Located below Estreito da Calheta, with nearby access to the expressways for ease of exploring Madeira, in a countryside location and with great views of the green hills and ocean, the beautifully appointed Villa Rouge is 3-bedroomed property that offers everything you …see more

from $132 / night

$921 / week

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avg. 1 hour 30 minutes

from $132 / 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 $57 / night

$397 - $556 / week

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Responds fast!
avg. 3 hours 45 minutes

from $57 / 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 $63 / night

$439 / week

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from $63 / 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 $68 / night

$465 / week

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from $68 / night

22

Vacation home accommodation

Calheta / Paul do Mar

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child friendly
Casa do Porto, A charming seaside home right at the sea. Casa do Porto is a typical fisherman home right at the ocean front. The village of Paul do Mar still fishes for the locals and you can go and experience the fisherman arriving and the selling of the fish right o …see more

from $40 / night

$278 - $397 / week

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from $40 / night

41

Calheta Vacation home rental

Madeira / Calheta

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
R&B Residence is a private rental full-equipped house located in a peaceful area in Calheta, the warmest area on the southwest coastline with a beautiful marina and two man-made golden sandy beaches. We are between the crowd and the nature. R&B Residence is a perfect ho …see more

from $40 / night

$279 / week

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Responds fast!
avg. 3 hours 14 minutes

from $40 / night

(4) Very Good 

38

Vacation home in Calheta

Madeira / Calheta

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
Recently build house, 2 bedrooms and 1 huge loft with double bed and 1 single bed. On one side we have an amazing sea view, to the other side we have mountains. Centrally located in the Madeira island, we are close to everywhere. Calheta beach is 5 minutes driving away …see more

from $46 / night

$465 - $624 / week

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avg. 1 hour 3 minutes

from $46 / night

(2) Excellent 

34

Prazeres Vacation home accommodation

Calheta / Prazeres

3 7 5 nights min

  • 3 bedrooms
  • sleeps 7
  • 5 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Private garden
Is a house where you can enjoy quietly of unique moments provided by the surrounding environment with all the comfort and security. «Leahouse» is a possessor of a pleasant green space surroundings where you can enjoy a distinct solar exposure. Surprise yourself with the …see more

from $46 / night

$318 / week

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Responds fast!
avg. 2 hours 29 minutes

from $46 / night

(2) Excellent 

15

Arco da Calheta Vacation apartment rental

Calheta / Arco da Calheta

1 2 6 nights min

  • 1 bedroom
  • sleeps 2
  • 6 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Private garden
The apartment is located in Arco da Calheta, a short distance from the centre of Calheta beach and the village. Has a breathtaking view over the Banana plantation, the Ocean and have everyday unforgettable sunsets. One bedroom, 1 bathroom, kitchen, lounge & dining area: …see more

from $59 / night

$413 / week

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avg. 11 minutes

from $59 / 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 $68 / night

$476 / week

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from $68 / night

(12) Very Good 

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

from $77 / night

$534 - $846 / week

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avg. 3 hours 10 minutes

from $77 / night

18

Calheta Vacation home rental

Madeira / Calheta

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden
Casa Simão has 2 double bedrooms and bathroom with shower. You can visit Calheta Beach, located 2 km away, Madeira International Airport is 48 km away. It is the perfect refuge for rest and tranquility, so you can enjoy a quiet and cozy holiday on the rural side of Ma …see more

from $29 / night

$199 / week

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Responds fast!
avg. 38 minutes

from $29 / 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 $59 / night

$413 / week

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from $59 / night

(7) Very Good 

23

Vacation cottage in Arco da Calheta

Calheta / Arco da Calheta

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 3 mi
  • Child friendly
Set in the lovely garden that is a veritable sun trap, this beautifully restored stone cottage is superbly positioned on the cliff top with outstanding views of the sea and coastline. Perfect for those that wish to experience the traditional Madeira lifestyle and be clo …see more

from $66 / night

$463 / week

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avg. 1 hour 30 minutes

from $66 / night

(1) Excellent 

10

Vacation apartment rental

Madeira / Calheta

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Nearest beach 4 mi
  • Private garden
Location— Location – Location - Casa Serena Apartments These tourist approved spacious fully equipped holiday rental apartments, with a breath taking south facing sea view, are located in the sunny south west of Madeira, on the side of the valley overlooking the banana …see more

from $57 / night

$397 / week

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from $57 / night

(2) Very Good 

22

Home rental in Jardim do Mar

Calheta / Jardim do Mar

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 0.3 mi
  • Child friendly
Casa das Pedras is a two storey village house built in 2006 It is situated at the edge of Jardim do Mar in an area known as the Pontinha or  little headland It is  reached on foot by a 200m path from the village square where there is a free car park. It has two doub …see more

from $77 / night

$536 - $893 / week

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Responds fast!
avg. 3 hours 21 minutes

from $77 / night

(2) Excellent 

23

Estreito da Calheta Vacation guest house rental

Calheta / Estreito da Calheta

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Typical Madeiran house in a quiet location This property is a typical Madeiran country house that has been completely and faithfully renovated. This picturesque house is very comfortable, spread over three levels, with 2 bedrooms, 1 bathroom, 1 spacious living/di …see more

from $63 / night

$439 - $598 / week

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from $63 / night

11

Faja da Ovelha Vacation home rental

Calheta / Faja da Ovelha

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • 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 $37 / night

$254 / week

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from $37 / 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 $194 / night

$1,354 / week

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from $194 / night

(1) Excellent 

16

Calheta Vacation home rental

Madeira / Calheta

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Excelent localization, in Calheta, with a sober view over the sea and near of various interess locals such as the marina of Calheta, the sandy beach, and the Centro de Artes Casa das Mudas, nomeated in 2005 to MIES VAN DER ROHE prize of architecture. Ideally located …see more

from $114 / night

$794 / week

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from $114 / night

(4) Very Good 

26

Vacation villa in Arco da Calheta

Calheta / Arco da Calheta

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
SISTER PROPERTY TO VILLA DO MAR I AND VILLA DO MAR II Located on a fajã (a piece of land at the foot of a cliff) in the sunny Calheta area, close to its sister villas (Villa do Mar I and Villa do Mar II) and slightly elevated, Vila do Mar III has been beautifully conve …see more

from $137 / night

$959 / week

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avg. 1 hour 30 minutes

from $137 / night

(5) Very Good 

32

Vacation cottage with swimming pool in Ponta do Pargo

Calheta / Ponta do Pargo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Solar do Pargo is situated in a romantic, rustic, idyllic and in direct contact with nature. Located on top of the hill where vision is dazzled with the sea and the surrounding green landscape. The house is built of stone, with large spaces. Private toilet with shower i …see more

from $69 / night

$478 / week

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avg. 2 hours 8 minutes

from $69 / night

27

Vacation villa rental

Calheta / Arco da Calheta

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
This is a 3 bedroom super luxury villa located in arco da calheta. As said before the property has 3 luxury modern style bedrooms, 4 luxurious modern bathrooms, new modern kitchen, laundry room, etc... The property was recently decorated with high quality furniture whic …see more

from $118 / night

$821 / week

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from $118 / night

(5) Excellent 

28

Vacation villa in Ponta do Pargo

Ponta do Pargo / Serrado

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Nearest beach 20 mi
  • Child friendly
  • Ask about pets
Fantastic villa and garden in a stunning location perched on top of the dramatic cliffs at the western tip of this delightful island The Quinta offers two large double rooms on the ground floor and one room up in the tower - all with 4 poster beds - all with ocean view. …see more

from $182 / night

$1,270 - $2,341 / week

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from $182 / night

30

Prazeres Vacation home rental

Calheta / Prazeres

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Car not necessary
Casa Pesquito is a newly renovated country house with all the amenities to enjoy your holiday in tranquility. The house is located very close to the local supermarket, as well as restaurants and bars, being ideal for anyone planning to travel without worries of finding …see more

from $34 / night

$238 / week

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Responds fast!
avg. 18 minutes

from $34 / 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 $65 / night

$454 - $534 / week

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from $65 / 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 $84 / night

$587 / week

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from $84 / night

39

Vacation villa with indoor pool, golf nearby in Arco da Calheta

Calheta / Arco da Calheta

3 7 5 nights min

  • 3 bedrooms
  • sleeps 7
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
A charming 5 star villa. A completely new villa in the market with 3 bedrooms ( the master suit bedroom has a private main bathroom with jacuzzi) with luxurious finishing and a fully loaded modern kitchen with dinning area and spotlights in the sitting area , dinning ar …see more

from $82 / night

$572 / week

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from $82 / night

(1) Excellent 

47

Vacation apartment accommodation

Calheta / Arco da Calheta

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Private garden
Modern apartment in a quiet location, only 15 minutes drive to the beach of Calheta and shops, 30 minutes from Funchal and 45 minutes from the airport. It is ideally located for touring the island , with easy access to the North and its fabulous landscapes via Ribeira …see more

from $63 / night

$437 - $675 / week

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from $63 / 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 $97 / night

$643 - $753 / week

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from $97 / night

(2) Excellent 

25

Vacation villa with swimming pool in Arco da Calheta

Calheta / Arco da Calheta

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the top of Arco da Calheta cliff, this Villa has the most astonishing and breathless view of Atlantic Ocean, not to mention, that you’ll have the great experience to see one of the most beautiful sunsets in the all Island. The house offers you three double s …see more

from $177 / night

$1,235 / week

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avg. 3 hours 14 minutes

from $177 / night

(1) Excellent 

16

Vacation home in Paul do Mar

Calheta / Paul do Mar

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Child friendly
House completely remodeled and well located 50 meters from the beach where you can have the possibility to swim or surf or simply enjoy the sea and the magnificent sun that shines all year round! The months of March to December is summer in Paul do Mar and although we a …see more

from $35 / night

$239 / week

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avg. 1 hour 58 minutes

from $35 / night

29

Villa rental in Arco da Calheta with swimming pool

Calheta / Arco da Calheta

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
*** New photos showing property renovation in January 2018. New Television (Curve screen, HD, internet connected). Our Villa is located in the rural southwest of Madeira, near Arco da Calheta, 40 minutes from Funchal airport. It is only a 5 minute drive away from the g …see more

from $157 / night

$1,100 - $2,909 / week

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avg. 1 hour 48 minutes

from $157 / night

(2) Excellent 

32

Vacation villa with shared pool, golf nearby in Estrela, Madeira

Calheta / Estrela, Madeira

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly
Set on the tranquil sunny hills above Calheta, and close to amenities, the present owner, Elisabeth, sympathetically restored and refurbished her great grandmothers cottages to create this lovely character air-conditioned villa. Relaxing by the tranquil pool and large …see more

from $93 / night

$651 / week

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avg. 1 hour 30 minutes

from $93 / night

(29) 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 $40 / night

$278 / week

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Responds fast!
avg. 2 hours 58 minutes

from $40 / night

(7) Excellent 

23

Vacation villa with shared pool, golf nearby in Calheta

Madeira / Calheta

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Offering outstanding 360º panoramic views of the sea and mountains, Casa do Julio is a traditional Madeiran house wonderfully located on a bluff overlooking Calheta beach, yet very private and tranquil. The owner has furnished it beautifully combing contemporary furnitu …see more

from $132 / night

$925 / week

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Responds fast!
avg. 1 hour 30 minutes

from $132 / night

(1) Excellent 

21

Vacation apartment in Arco da Calheta

Calheta / Arco da Calheta

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
The Casa Serramar offers all the amenities for a peaceful holidays. It has two apartments, both with a kitchen, a comfortable living room, two bedrooms and a bathroom. Situated 10 minutes from the beach of Calheta, 15 minutes from access to Rabaçal, 42 minutes of natura …see more

from $63 / night

$437 / week

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Responds fast!
avg. 2 hours 28 minutes

from $63 / night

(1) Excellent 

62

Vacation home in Jardim do Mar

Calheta / Jardim do Mar

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
Casa típica, com muita privacidade. Vista para o Oceano Atlântico. Construída no século XIX e construída novamente no século XXI, toda em pedra e madeira. Muita paz e sossego. Situada numa vila muito característica da Ilha da Madeira, principalmente pelo surf. Os Turist …see more

from $40 / night

$279 / week

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from $40 / 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 $210 / night

$1,462 / week

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from $210 / night