50 Best Vacation Rentals in Calheta - Holiday Lettings - Cabins

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Arco da Calheta
162 properties
Estreito da Calheta
55 properties
Faja da Ovelha
34 properties
Ponta do Pargo
33 properties
Prazeres
29 properties
Paul do Mar
19 properties
Jardim do Mar
9 properties

Calheta

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400 Vacation rentals

(8) Excellent 

26

Villa rental in Calheta

Madeira / Calheta

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
SISTER PROPERTY DO VILLA DO MAR I (5307248) AND VILLA DO MAR III (6619756) Located on a fajã (a piece of land at the foot of a cliff) in the sunny Calheta area, and perched overlooking the ocean, Villa do Mar II has been beautifully converted from a farmers barn into a …see more

from $127 / night

$889 - $2441 / week

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avg. 2 hours 15 minutes

from $127 / night

23

Vacation villa in Prazeres

Calheta / Prazeres

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
Excellent country house fully restored, true paradise and that's why it was called Angels in Paradise. locate in the west side of Madeira Island in a village called Calheta, Angels in Paradise offers luxury place with private pool, outside patio with BBQ beautiful garde …see more

from $101 / night

$697 - $1845 / week

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avg. 11 minutes

from $101 / 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 $179 / night

$1248 / week

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from $179 / night

(4) 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 $64 / night

$445 - $523 / week

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from $64 / night

(14) Excellent 

24

Calheta Vacation cottage rental

Madeira / Calheta

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
The Thebaida do Massapez is located in Fajã da Ovelha, Calheta municipality Has 2 rooms and seating for 6 people. Is situated in an area which is a private road, erma and is deployed to about 60 metres of road. The House is completely private, whose major asset is the t …see more

from $73 / night

$502 - $858 / week

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avg. 24 minutes

from $73 / night

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 $112 / night

$780 / week

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from $112 / night

(24) 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 $251 / night

$1555 - $2958 / week

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avg. 2 hours 42 minutes

from $251 / night

35

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 $46 / night

$320 / week

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from $46 / night

24

Prazeres Vacation villa rental

Calheta / Prazeres

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • 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 Sky Villa has outstanding panoramic views over the green countryside to the sea and coast, an inside/out …see more

from $123 / night

$229 - $697 / week

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avg. 1 hour 44 minutes

from $123 / night

(2) Very Good 

15

Arco da Calheta Vacation cottage rental

Calheta / Arco da Calheta

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Casa do Pombal is a family property that once belonged to parents of the current owner. It was built in the early twentieth century, when houses are still built with stone. Thus preserved this type of construction. Is a house located in a pleasant, quiet and surrounded …see more

from $125 / night

$875 / week

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avg. 1 hour 39 minutes

from $125 / night

(1) Very Good 

39

Vacation villa in Arco da Calheta

Calheta / Arco da Calheta

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
SISTER PROPERTY DO VILLA DO MAR I (5307248) AND VILLA DO MAR II (5313080) 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 bee …see more

from $127 / night

$889 - $2558 / week

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avg. 2 hours 15 minutes

from $127 / night

(2) Excellent 

24

Home rental in Arco da Calheta with golf nearby

Calheta / Arco da Calheta

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
A charming new villa house with total relaxation and excellent views of the ocean and tipical town mountain and centre views. The area of the "Rose villa" house has a total of 400 m2 where the total construction area covers 300 m2 and was built in the year 2012; …see more

from $81 / night

$562 / week

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from $81 / night

(20) Excellent 

18

Vacation villa in Arco da Calheta

Calheta / Arco da Calheta

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
This luxurious villa located on the edge of Loreto, a traditional Madeiran village above Arco da Calheta. It is equally as perfect for a couple wanting a romantic sojourn as it is for a family wanting quality time relaxing and enjoying each other. The three bedrooms, h …see more

from $101 / night

$699 - $1531 / week

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avg. 1 hour 37 minutes

from $101 / night

11

Prazeres Vacation villa rental

Calheta / Prazeres

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 3-bedroom Eden Rose Villa has outstanding panoramic views over the green countryside to the sea and coast, an inside/ou …see more

from $223 / night

$780 - $2714 / week

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avg. 2 hours 15 minutes

from $223 / night

(2) Excellent 

25

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 $179 / night

$1248 - $2301 / week

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from $179 / night

29

Villa rental in Arco da Calheta

Calheta / Arco da Calheta

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A 4 bedroom luxury villa located in Arco da Calheta. the property has 4 luxury modern style bedrooms, luxurious modern bathrooms and an open-garden bathroom with shower new modern kitchen, laundry room, etc... The property was recently decorated with high quality furni …see more

from $199 / night

$1393 - $2886 / week

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from $199 / night

(1)  

10

Home rental in Arco da Calheta with swimming pool

Calheta / Arco da Calheta

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
3 Bedrooms, 2 Bathroom with breath taking mountain and sea view Cool, calm and sophisticated with a youthful edge, each with their own theme, these functional homes are enveloped in light and comfort. Crisp white walls, timber floors and high ceilings create a style as …see more

from $90 / night

$624 - $1560 / week

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from $90 / night

(1) Excellent 

24

Vacation villa with swimming pool in Estrela, Madeira

Calheta / Estrela, Madeira

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Air conditioning
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 $89 / night

$617 - $1825 / week

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avg. 2 hours 15 minutes

from $89 / night

(4) Excellent 

20

Vacation cottage in Arco da Calheta

Calheta / Arco da Calheta

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
A delightful traditional Madeira stone cottage and garden on the clifftop with breathtaking views of the sea and coastline, in the sun-baked area of Calheta. Set in the lovely garden that is a veritable suntrap, this beautifully restored stone cottage is superbly posit …see more

from $45 / night

$312 - $921 / week

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avg. 2 hours 15 minutes

from $45 / night

29

Villa rental in Arco da Calheta

Calheta / Arco da Calheta

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
With an infinity style pool that reaches into the living area, and located in the sunniest area of Madeira, this delightful villa offers tranquillity, outstanding views and close access to the sea. Located on a fajã (a piece of land at the foot of a cliff) in the sunny …see more

from $132 / night

$921 / week

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from $132 / night

(6) Excellent 

Certificate of Excellence

37

Prazeres Vacation villa rental

Calheta / Prazeres

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
A very large top quality 4-bedroomed villa with pool 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 expressway for e …see more

Certificate of Excellence

from $308 / night

$858 - $3463 / week

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avg. 2 hours 15 minutes

from $308 / night

10

Vacation home in Ponta do Pargo

Calheta / Ponta do Pargo

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
De uma antiga adega, onde se guardavam para além do vinho, as ferramentas agrícolas, reconstruiu-se a Casa da Cascata, mantendo esta o seu traço original em pedra. A sua decoração está ligada a um dos quatro elementos, a Água, caracterizando-se como simples e rústica. E …see more

from $70 / night

$484 / week

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from $70 / night

(3) 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 $78 / night

$546 / week

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avg. 2 hours 10 minutes

from $78 / 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 $190 / night

$1326 / week

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from $190 / night

(10) Excellent 

Certificate of Excellence

24

Calheta Vacation villa rental

Madeira / Calheta

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Excellent country house fully restored, true paradise and that's why it was called Angels in Paradise. locate in the east side of Madeira Island in a village called Calheta, Angels in Paradise offers luxury place with private pool, outside patio with BBQ beautiful garde …see more

Certificate of Excellence

from $95 / night

$647 - $1790 / week

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avg. 32 minutes

from $95 / 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 $62 / night

$429 / week

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Responds fast!
avg. 2 hours 29 minutes

from $62 / night

(10) Very Good 

26

Vacation home in Paul do Mar

Calheta / Paul do Mar

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
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 $56 / night

$390 / week

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avg. 2 hours 43 minutes

from $56 / night

19

Faja da Ovelha Vacation guest house rental

Calheta / Faja da Ovelha

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
Brand new, is located on a property with swimming pool, parking, garden, BBQ. Lombada dos Marinheiros- Fajã da Ovelha (location) in which it is famous for its beautiful sunset and the fantastic view of the sea, sometimes hidden by clouds forming a white "blanket" that p …see more

from $51 / night

$351 / week

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from $51 / night

(1) Very Good 

24

Home rental in Ponta do Pargo

Ponta do Pargo / Serrado

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
If you want a quiet place to rest from your day to day or just a place where you can enjoy nature in a family environment then Heaven Villa is the place for you. Located in the picturesque village of Ponta do Pargo the Heavens Villa provides a quiet and pleasant …see more

from $67 / night

$335 / week

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from $67 / night

(2) Excellent 

22

Vacation home in Calheta

Madeira / Calheta

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Child friendly
  • Ask about pets
  • Private garden
«House Neves ' is a nice area located in Prazeres, Calheta-Madeira, with an outdoor space with approximately called Casa con Estilo of fruit trees and herbs. It is a house where you can quietly enjoy unique moments provided by the surroundings in comfort and safety. ' N …see more

from $37 / night

$258 / week

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avg. 2 hours 48 minutes

from $37 / night

(4) Very Good 

33

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 $74 / night

$515 / week

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from $74 / night

15

Home rental in Calheta

Madeira / Calheta

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
House framed the nature of Calheta. Near taken along the walks, but still very close to the Ocean and the Best Beach Calheta (with sand). Much peace and tranquility where you can enjoy the sound of trees and birds with the traditional population of Madeira which is stil …see more

from $34 / night

$234 / week

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from $34 / night

(4) Excellent 

26

Vacation apartment rental

Calheta / Arco da Calheta

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
This is a beautiful and very popular apartment that has breathtaking panoramic sea views and stunning sunsets over the adjacent banana plantation. All the rooms open onto a large balcony where you can relax and enjoy the views with a glass of Madeira wine. Penthouse apa …see more

from $75 / night

$523 / week

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from $75 / night

(8) Excellent 

27

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 $78 / night

$546 / week

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from $78 / night

32

Cottage rental in Faja da Ovelha

Calheta / Faja da Ovelha

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Raposeira 1 CHLOE CHLOE 2 were built in general for all kinds of customers, they are in love with nature, scenery, hiking, water sports or just a relaxing stay in a very quiet, charming and elegant area. CHLOE 2 is another house in front of which can accommodate up to …see more

from $112 / night

$780 / week

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avg. 3 hours 34 minutes

from $112 / night

(2) Very Good 

24

Calheta Vacation villa rental

Madeira / Calheta

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • 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 $101 / night

$663 - $1170 / week

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Responds fast!
avg. 3 hours 37 minutes

from $101 / night

(3) Very Good 

24

Vacation apartment in Arco da Calheta

Calheta / Arco da Calheta

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
Somos um casal de 60 anos que decidiram compartilhar o topo da nossa casa com pessoas como Ilha da Madeira, o apartamento é completamente independente da nossa casa, só têm em comum o portão principal. A área tem um bom acesso ao mar, e as belezas naturais do litoral, t …see more

from $39 / night

$273 / week

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from $39 / night

(22) 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 $39 / night

$273 - $312 / week

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Responds fast!
avg. 2 hours 47 minutes

from $39 / night

(2) 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 3 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 $83 / night

$578 / week

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from $83 / night

(1) Excellent 

30

Vacation villa rental

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
This is a 3 bedroom super luxury villa located in arco da calheta in an urbanization. As said before the property has 3 luxury modern style bedrooms, 3 luxurious modern bathrooms, new modern kitchen, laundry room, etc... The property was recently decorated with high qua …see more

from $115 / night

$804 / week

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from $115 / night