50 Best Vacation Rentals in Calheta - Holiday Lettings - Cabins

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Arco da Calheta
151 properties
Estreito da Calheta
49 properties
Faja da Ovelha
40 properties
Ponta do Pargo
28 properties
Prazeres
21 properties
Paul do Mar
16 properties
Jardim do Mar
12 properties

Calheta

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372 Vacation rentals

(2) 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 $44 / night

$302 - $761 / week

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from $44 / night

(2) 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 $140 / night

$980 - $2148 / week

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from $140 / night

(8) Excellent 

13

Vacation studio in Ponta do Pargo

Ponta do Pargo / Serrado

Studio 2 1 night min

  • Studio
  • Sleeps 2
  • 1 night min
  • Nearest beach 22 mi
  • Child friendly
Combine your visit to Madeira's capital Funchal with a visit to Ponta do Pargo, a small village surrounded with unspoilt nature & countryside landscapes typical of Madeira's South-West Coast, located within a 1 hour drive from Funchal'Our farm was  …see more

from $33 / night

$194 - $415 / week

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from $33 / night

(1) Excellent 

15

Arco da Calheta Vacation apartment rental

Calheta / Arco da Calheta

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 a  …see more

from $56 / night

$392 / week

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from $56 / night

22

Vacation villa with swimming pool in Arco da Calheta

Calheta / Arco da Calheta

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
This stunning villa, built only four years ago, has a 9 x 6 metre swimming pool with magnificent views of the ocean and mountains and a large terrace which also surrounds the pool. It has interior designed furnishings, established gardens, plenty of secure parking at th  …see more

from $178 / night

$1244 - $2057 / week

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from $178 / night

(8) Excellent 

25

Villa rental in Faja da Ovelha with swimming pool

Calheta / Faja da Ovelha

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Excellent country house fully restored, true paradise and that's why it was called ANGELS IIN PARADISE 2. Locate in the east side of Madeira Island in a place called Fajã da Ovelha, Angels in Paradise 2 offers a great place with private pool, outside patio with BB  …see more

from $70 / night

$485 - $1081 / week

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from $70 / night

(19) 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 $243 / night

$1502 - $2858 / week

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from $243 / 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 $235 / night

$1461 - $1651 / week

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from $235 / night

(8) 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  …see more

from $91 / night

$619 - $1714 / week

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from $91 / night

21

Calheta / Prazeres

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Private garden

 …see more

from $33 / night

$227 - $566 / week

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from $33 / 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 litor  …see more

from $38 / night

$264 / week

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from $38 / night

(1) Excellent 

29

Vacation villa rental

Calheta / Arco da Calheta

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night 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 $122 / night

$852 / week

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from $122 / night

22

Madeira / Calheta

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Private garden

 …see more

from $27 / night

$189 - $347 / week

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from $27 / night

(9) Very Good 

41

Calheta / Jardim do Mar

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

 …see more

from $102 / night

$897 - $1420 / week

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from $102 / night

(4) Excellent 

37

Prazeres Vacation villa rental

Calheta / Prazeres

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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 $298 / night

$679 - $3346 / week

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from $298 / 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 $193 / night

$1346 - $2788 / week

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from $193 / night

(2) Excellent 

28

Calheta / Ponta do Pargo

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from $58 / night

$400 / week

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from $58 / night

26

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Welcome to our property! This beautiful country house with an oceanfront view is located in the heart of Arco da Calheta (Council of Calheta) and within a few minutes of distance you will find absolutely everything you need, like a supermarket, restaurants, bars and  …see more

from $46 / night

$313 / week

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from $46 / night

(24) Very Good 

24

Vacation villa in Estreito da Calheta

Calheta / Estreito da Calheta

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
The Villa is located in one of the oldest Parishes in Madeira .It is quiet and peaceful and a great place to relax and unwind. However there is plenty in the surrounding area to see and do during your stay and lots to do for the more active people.The villa has  …see more

from $79 / night

$553 - $909 / week

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from $79 / night

(2) Very Good 

27

Vacation villa in Estreito da Calheta

Calheta / Estreito da Calheta

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
Located below Estreito da Calheta, with nearby access to the expressways for ease of exploring Madeira, in a quiet countryside location and with great views of the green hills and ocean, the beautifully appointed Villa Rouge is 3-bedroomed property that offers everythin  …see more

from $118 / night

$822 - $2291 / week

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from $118 / 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  …see more

from $162 / night

$1131 / week

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from $162 / 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, bott  …see more

from $71 / night

$481 / week

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from $71 / night

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 be  …see more

from $123 / night

$859 - $2472 / week

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from $123 / night

20

Calheta / Arco da Calheta

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $162 / night

$1131 - $2637 / week

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from $162 / night

16

Arco da Calheta Vacation villa rental

Calheta / Arco da Calheta

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
This rebuilt stone Quinta set in a friendly village has ocean views and all the amenities for a large family holiday with a 9 x 6 metre swimming pool, a large shaded terrace for al fresco dining, a barbecue room and a four car garage. It is tastefully equipped with a fu  …see more

from $143 / night

$998 - $1244 / week

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from $143 / night

(17) 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 $96 / night

$667 - $1396 / week

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from $96 / 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 2006It 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 $64 / night

$445 - $623 / week

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from $64 / night

(1) Excellent 

12

Calheta / Arco da Calheta

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $54 / night

$377 / week

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from $54 / night

(1) Excellent 

29

Calheta / Prazeres

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 4 mi
  • Child friendly
  • Ask about pets

 …see more

from $60 / night

$415 - $490 / week

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from $60 / night

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 $92 / night

$641 - $1131 / week

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from $92 / night

(4) Excellent 

17

Vacation apartment rental

Calheta / Arco da Calheta

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $73 / night

$505 / week

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from $73 / night

(1) Excellent 

22

Madeira / Calheta

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from $33 / night

$227 / week

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from $33 / night

(8) Very Good 

24

Estreito da Calheta Vacation villa rental

Calheta / Estreito da Calheta

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • 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 $73 / night

$507 - $1023 / week

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from $73 / night

(7) 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 $32 / night

$219 - $294 / week

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from $32 / night

20

Home rental in Calheta

Madeira / Calheta

2 3 1 night min

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

from $45 / night

$312 / week

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from $45 / night

(11) Excellent 

24

Madeira / Calheta

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool

 …see more

from $70 / night

$481 - $822 / week

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from $70 / night

31

Arco da Calheta Vacation villa rental

Calheta / Arco da Calheta

3 4 1 night min

  • 3 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden
NOW THE VILLA HAS covered POOL, air condicioned AND SAUNA!!! 2 Bedroom villa with capacity for 4 people. This is a 2 bedroom super luxury villa located in Arco da Calheta in a private urbanization. As said before the property has 2 luxury modern style bedrooms, 3 luxu  …see more

from $253 / night

$1771 / week

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from $253 / night

(4) Excellent 

24

Vacation villa in Arco da Calheta

Calheta / Arco da Calheta

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Two floors independent house (underground parking garage) with 3 air-conditioned rooms, 3 bathrooms, 1 with whirlpool bath and one with hydromassage power shower , a living room and dining open space. Garden overlooking the sea and mountains, barbecue, parking, heated p  …see more

from $176 / night

$969 - $1836 / week

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from $176 / night

12

Vacation cottage in Ponta do Pargo

Calheta / Ponta do Pargo

3 2 1 night min

  • 3 bedrooms
  • Sleeps 2
  • 1 night min
  • Nearest beach 23 mi
  • Child friendly
Combine your visit to Madeira's capital Funchal with a visit to Ponta do Pargo, a small village surrounded with unspoilt nature & countryside landscapes typical of Madeira's South-West Coast, located within a 1 hour drive from Funchal'Our farm was  …see more

from $38 / night

$216 - $415 / week

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from $38 / night

(1) Very Good 

17

Jardim do Mar Vacation apartment rental

Calheta / Jardim do Mar

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 0.3 mi
  • Child friendly
Two bedrooms, one with double bed, one with twin beds. Two bathrooms each with WC, bidet, handbasin, bath and shower. Lounge with balcony and view of sea and mountains. Fully fitted and equipped modern open plan kitchen with electric oven, electric hob, microwave, refr  …see more

from $51 / night

$356 / week

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from $51 / night