50 Best Vacation Rentals in Calheta - Holiday Lettings - Cabins

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Arco da Calheta
164 properties
Estreito da Calheta
49 properties
Ponta do Pargo
33 properties
Faja da Ovelha
33 properties
Prazeres
25 properties
Paul do Mar
16 properties
Jardim do Mar
9 properties

Calheta

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387 Vacation rentals

(3) Very Good 

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

$314 - $793 / week

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from $45 / 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

$701 - $1856 / week

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from $101 / night

(22) 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 $253 / night

$1564 - $2976 / week

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from $253 / night

(19) 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 $103 / night

$715 - $1567 / week

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from $103 / 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

$628 - $1569 / 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

$620 - $1836 / week

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from $89 / 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 $126 / night

$880 / week

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from $126 / night

(12) 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

$505 - $863 / week

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from $73 / 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 $133 / night

$926 / week

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from $133 / night

(1) Excellent 

26

Vacation cottage in Arco da Calheta

Calheta / Arco da Calheta

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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

$460 - $572 / week

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from $68 / night

24

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • 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 $73 / night

$494 - $572 / week

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from $73 / 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 $201 / night

$1401 - $2903 / week

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from $201 / night

(11) Very Good 

20

Vacation cottage in Calheta

Madeira / Calheta

2 3 6 nights min

  • 2 bedrooms
  • Sleeps 3
  • 6 nights min
  • Nearest beach 2 mi
  • Suitable for children age 5+
  • Car not necessary
A beautiful fully equipped Madeira traditional holiday cottage is located in an attractive village of Arco da Calheta, situated in the south west of the island. This holiday home is absolutely unique and gives you all the peaceful and relaxing holidays; because of being …see more

from $40 / night

$275 - $354 / week

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from $40 / 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 $79 / night

$550 / week

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from $79 / night

(21) Very Good 

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

from $40 / night

$275 - $314 / week

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from $40 / 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

$236 / week

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from $34 / night

27

Massapez Vacation apartment rental

Calheta / Massapez

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Child friendly
The Casal São João Cottages is a typical Madeiran stone house located in the west of the Madeira Island in Fajã da Ovelha - Calheta, about 58 km from the airport of Santa Cruz and 42 km from the city of Funchal. This construction is dated from the year of 1930 and comp …see more

from $40 / night

$275 / week

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from $40 / night

(9) Excellent 

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

from $96 / night

$650 - $1800 / week

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from $96 / night

26

Prazeres Vacation home rental

Calheta / Prazeres

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Pet friendly
Welcome to our property! Breathe Madeira… Immerse yourself in a unparalleled beauty. Step out into terrace and experience the pure air in the parish of Prazeres the way you've always imagined. You have lots of space to enjoy your holidays in this property. Every inch o …see more

from $37 / night

$258 / week

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from $37 / 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 $57 / night

$393 / week

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from $57 / night

(3) Excellent 

30

Arco da Calheta Vacation villa rental

Calheta / Arco da Calheta

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Offering panoramic views over the Atlantic Ocean, this recently restored house is located in a privileged area of Calheta, Madeira Island. Atlantis Country House is 33 km from Funchal city centre. Offering rustic-style architecture, the house combines exposed sto …see more

from $68 / night

$471 - $785 / week

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from $68 / night

(7) Very Good 

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 $128 / night

$895 - $2456 / week

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from $128 / night

(3) 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 $67 / night

$463 / week

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from $67 / night

25

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
  • Swimming pool
  • Child friendly
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 golden sandy beach in Calheta. * Our Villa has its own private, south facing, salt water swimming pool (9m x 4m) and …see more

from $119 / night

$830 - $3732 / week

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from $119 / night

22

Vacation home in Calheta

Madeira / Calheta

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Private garden
«Laurishouse» is a house next to the Nature, in the pleasures, CHARTER/license certified LOCAL HOUSING paragraph 4/12 of 4/3/2012 in the parish of Prazeres Calheta-Madeira, with a landscaped green space about Kansas City with flowers, fruit trees, aromatic herbs, etc. I …see more

from $34 / night

$236 / week

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from $34 / night

(5) Excellent 

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

from $310 / night

$863 - $3484 / week

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from $310 / night

(3) Excellent 

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

from $146 / night

$1020 - $2236 / week

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from $146 / night

29

Villa rental in Calheta

Madeira / Calheta

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $57 / night

$393 - $550 / week

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from $57 / night

(1) Very Good 

29

Villa rental in Arco da Calheta with golf nearby

Calheta / Arco da Calheta

4 6 5 nights min

  • 4 bedrooms
  • Sleeps 6
  • 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 a private urbanization. As said before the property has 3 luxury modern style bedrooms, 3 double bed, and another room with a single bed, also we have a sofa bed for more 1 person, 2 luxurious modern b …see more

from $116 / night

$809 / week

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from $116 / 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

$518 / week

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from $74 / 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 $180 / night

$1256 / week

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from $180 / night

(1) 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

$667 - $1177 / week

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from $101 / night

(2) Excellent 

25

Vacation villa in Ponta do Pargo

Ponta do Pargo / Serrado

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 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 $169 / night

$1177 - $2113 / week

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from $169 / night

(3) 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

$448 - $526 / week

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from $64 / night

45

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 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 $68 / night

$471 - $1130 / week

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from $68 / 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 $65 / night

$455 - $707 / week

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from $65 / 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. < …see more

from $65 / night

$455 - $637 / week

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from $65 / 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 $113 / night

$785 / week

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from $113 / 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 $40 / night

$275 / week

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from $40 / night

(11) Very Good 

42

Beach hut rental in Jardim do Mar with swimming pool

Calheta / Jardim do Mar

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • 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

from $180 / night

$1256 / week

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from $180 / night

1