50 Best Vacation Rentals in Calheta - Holiday Lettings - Cabins

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1,613 Vacation rentals

(3) Very Good 

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 $45 / night

$395 - $553 / week

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avg. 3 hours 17 minutes

from $45 / night

(9) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $131 / night

$916 / week

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Responds fast!
avg. 1 hour 7 minutes

from $131 / night

(9) 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 $147 / night

$1,026 - $1,342 / week

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from $147 / night

46

Vacation home in Faja da Ovelha

Calheta / Faja da Ovelha

3 5 4 nights min

  • 3 bedrooms
  • sleeps 5
  • 4 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Private garden
The "Casa do Leão" is the ideal place for a peaceful and luxurious stay in Madeira. Located on a Hillside in Fajã da Ovelha, you will be able to observe the Atlantic Ocean as well as the sunset all throughout the house, mainly on its three balconied or even from the gar …see more

from $68 / night

$474 / week

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avg. 17 minutes

from $68 / 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

(18) 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» The villa, is called the "house where the mountain meets the sea" because of, in one house, can enjoy at the same time, the sea and the rustic mountain nature, this because the 1st floor is the pool area and solarium where you can …see more

Certificate of Excellence

from $124 / night

$868 / week

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avg. 2 hours 1 minutes

from $124 / night

22

Vacation home accommodation

Calheta / Paul do Mar

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • 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

$277 - $561 / week

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from $40 / night

(9) Excellent 

Certificate of Excellence

29

Prazeres Vacation villa rental

Calheta / Prazeres

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 6 mi
  • Swimming pool
  • Child friendly
This superb, very large luxury 4-bedroomed villa with pool is set within an expansive garden and lawn in a quiet and tranquil location with superb uninterrupted views of the slopes and ocean. Located in Prazeres close to facilities, it offers easy access to the express …see more

Certificate of Excellence

from $127 / night

$884 / week

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avg. 1 hour 7 minutes

from $127 / 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 $240 / night

$1,687 / week

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from $240 / night

(13) 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 $74 / night

$518 - $881 / week

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avg. 3 hours 6 minutes

from $74 / night

(6) 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 $254 / night

$2,036 / week

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avg. 3 hours 46 minutes

from $254 / night

(7) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from $12 / night

$79 / week

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avg. 1 hour 7 minutes

from $12 / 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 $36 / night

$253 / week

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avg. 44 minutes

from $36 / 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 $57 / night

$395 / week

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avg. 3 hours 14 minutes

from $57 / night

(1) Excellent 

24

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about pets
  • Private garden
The Tree is a unique piece of art. It is a place where even corners have a special touch. It is the place in which it’s possible to sleep inside art and beauty allied with sustainability and design. Super cozy! The house was built with recycled materials such as, bottle …see more

from $74 / night

$496 / week

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from $74 / 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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avg. 2 hours 58 minutes

from $40 / 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

$1,094 - $2,892 / week

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avg. 2 hours 4 minutes

from $157 / night

(1) Excellent 

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 $62 / night

$434 / week

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from $62 / night

(8) Very Good 

10

Calheta Vacation villa rental

Madeira / Calheta

3 7 5 nights min

  • 3 bedrooms
  • sleeps 7
  • 5 nights min
  • Swimming pool
  • Child friendly
Cottage modern style used for vacation, located 2 km from the sea, in a quiet area overlooking the sea. Great outdoor space to enjoy the sunny afternoons, which includes pool and Jacuzzi and even a barbecue. The house has wi-fi internet. House in a very quiet location …see more

from $102 / night

$670 - $1,143 / week

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avg. 1 hour 56 minutes

from $102 / 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 $85 / night

$592 / week

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from $85 / night

(5) Very Good 

37

Arco da Calheta Vacation cottage rental

Calheta / Arco da Calheta

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
Stone rocks house with 1 bedrooms. Capacity one double bed 1 bathroom. BBQ, beautiful direct ocean view close to levadas, pool. big garden with flowers of 2000 m2 Madeira self catering : Madeira self catering book holiday homes in Portugal Madeira book villas in …see more

from $51 / night

$355 / week

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from $51 / night

(3) Very Good 

51

Villa rental in Arco da Calheta with golf nearby

Calheta / Arco da Calheta

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Large balcony, terrace and very big glass windows to watch and enjoy all day sunshine and sunsets of sun go down over the sea. Sleeps 8 - 4 bedrooms. Our beautiful stone Villa 'Sunshine' is just 25 minutes drive from Funchal on excellent motorway - Via Rapida. Our frien …see more

from $100 / night

$695 / week

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from $100 / night

(3) Very Good 

27

Vacation villa with shared pool, golf nearby in Prazeres

Calheta / Prazeres

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly
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 $131 / night

$916 / week

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avg. 1 hour 7 minutes

from $131 / night

(34) 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 $265 / night

$1,685 - $3,105 / week

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avg. 2 hours 58 minutes

from $265 / night

29

Vacation villa in Arco da Calheta

Calheta / Arco da Calheta

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This is a 3 bedroom super luxury villa located in Arco da Calheta in a private urbanization. As said before the property has 3 luxury modern style bedrooms, 3 double bed, 2 luxurious modern bathrooms, new modern kitchen, laundry room, etc... The property was recently de …see more

from $136 / night

$947 / week

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Responds fast!
avg. 3 hours 29 minutes

from $136 / 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

$277 / week

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from $40 / night

36

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 $88 / night

$616 / week

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from $88 / night

(12) Excellent 

14

Vacation cottage in Estrela, Madeira

Calheta / Estrela, Madeira

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Nearest beach 3 mi
  • Child friendly
Palheiro Cottage has an 'Alojamento Local' Licence registration number Calheta - 13/12 and is fully insured. The cottage stands on a ridge and the views are breathtaking. The lounge/dining area/kitchen are all open plan on the first floor and encompass a large balcony …see more

from $59 / night

$411 / week

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avg. 2 hours 34 minutes

from $59 / night

(5) Excellent 

Certificate of Excellence

36

Villa rental in Arco da Calheta with shared pool, golf nearby

Calheta / Arco da Calheta

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
Perfectly located amidst banana trees, close to the sunny resort of Calheta, with superb panoramic views of the sea, The Designhouse is a fabulous contemporary villa beautifully designed by a British architect as the perfect holiday home. Thought has been put into every …see more

Certificate of Excellence

from $131 / night

$916 / week

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Responds fast!
avg. 1 hour 7 minutes

from $131 / night

37

Vacation villa in Calheta

Madeira / Calheta

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child friendly
  • Private garden
Wood Lovers Villa is perfectly decorated and lies in an elevated position within the scenic Calheta Bay which is just a few minutes' drive to this popular village. This luxurious 3 bedroom villa enjoys stunning views over the sea and benefits from a beautiful Swimming p …see more

from $181 / night

$1,263 / week

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from $181 / 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

(3) Very Good 

31

Arco da Calheta Vacation villa rental

Calheta / Arco da Calheta

4 9 5 nights min

  • 4 bedrooms
  • sleeps 9
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
This is a 4 bedroom luxury villa located in Arco da Calheta. As said before the property has 4 luxury modern style bedrooms, 3 luxurious modern bathrooms and an open-garden bathroom with shower new modern kitchen, laundry room, etc... The property was recently decorated …see more

from $116 / night

$810 / week

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from $116 / night

26

Home rental in Arco da Calheta with golf nearby

Calheta / Arco da Calheta

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
The summer 2011 completed holiday home - house of peace and tranquility - is above the center Calhetas, in the district of Calheta to approximately 400 meters. Here you have a wonderful panoramic view of the mountains, the sea and the sunset. The house has a walk-sqm li …see more

from $91 / night

$632 / week

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from $91 / 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 $45 / night

$316 / week

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from $45 / 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 $68 / night

$473 / week

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Responds fast!
avg. 1 hour 49 minutes

from $68 / night

(1) Excellent 

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

$568 / week

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from $82 / night

(1) Excellent 

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 $34 / night

$237 / week

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Responds fast!
avg. 31 minutes

from $34 / 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 $113 / night

$789 / week

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avg. 3 hours 36 minutes

from $113 / night

(1) Excellent 

27

Arco da Calheta Vacation apartment rental

Calheta / Arco da Calheta

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child friendly
Mao-Cheia house is a one bedroom apartment situated in a very quiet place in Calheta. You can reach the nearest beaches (Madalena do Mar and Calheta) in just 10 minutes. You can also get to the mountains in 10 minutes. The house has a fantastic network of trails and lev …see more

from $43 / night

$300 - $442 / week

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from $43 / night

22

Arco da Calheta Vacation villa rental

Calheta / Arco da Calheta

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • 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 $170 / night

$1,190 / week

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avg. 3 hours 14 minutes

from $170 / night