50 Best Vacation Rentals in Calheta - Holiday Lettings - Cabins

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Arco da Calheta
150 properties
Estreito da Calheta
47 properties
Faja da Ovelha
38 properties
Ponta do Pargo
27 properties
Prazeres
22 properties
Paul do Mar
13 properties
Jardim do Mar
12 properties

Calheta

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368 Vacation rentals

(20) 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 $241 / night

$1493 - $2840 / week

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from $241 / night

(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 $43 / night

$300 - $757 / week

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from $43 / night

(25) 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 $77 / night

$536 - $880 / week

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from $77 / night

(1) Excellent 

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 $38 / night

$263 / week

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from $38 / night

(15) Excellent 

34

Calheta Vacation villa rental

Madeira / Calheta

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
License Nº 20394/AL by Portugal Tourism Calheta Orchid House is situated in a quiet and tranquil district of Calheta, surrounded by small fields and gardens with typical Madeira Levada irrigation. In the house are available: Two spacious bedroom each with queen s  …see more

from $49 / night

$337 - $674 / week

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from $49 / 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

$974 - $2134 / week

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from $140 / night

(8) Excellent 

25

Villa rental in Faja da Ovelha with swimming pool

Calheta / Faja da Ovelha

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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 w  …see more

from $70 / night

$482 - $1074 / week

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from $70 / 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  …see more

from $81 / night

$546 - $1772 / week

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from $81 / 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 $33 / night

$225 - $278 / week

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from $33 / night

(2) 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 $59 / night

$412 - $487 / week

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from $59 / 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 $93 / night

$646 - $1352 / week

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from $93 / night

(1) Excellent 

22

Madeira / Calheta

4 8 5 nights min

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

 …see more

from $36 / night

$248 / week

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from $36 / night

(2) Excellent 

27

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

$405 / week

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from $58 / night

83

Vacation home in Estreito da Calheta

Calheta / Estreito da Calheta

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This house is brandnew and built with the latest stantards of confort. 2 bedrooms, 2 bathrooms, an outdoor pool with panoramic seaview The house has spacious kitchen and living room open plan with about 50 sqm. Here is also simultaneously the large kitchen, reading are  …see more

from $118 / night

$824 - $963 / week

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from $118 / night

22

Madeira / Calheta

1 4 7 nights min

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

 …see more

from $33 / night

$225 / week

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from $33 / night

(4) Very Good 

33

Arco da Calheta Vacation cottage rental

Calheta / Arco da Calheta

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night 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 m2Madeira self catering : Madeira self catering book holiday homes in Portugal Madeira book villas in  …see more

from $48 / night

$330 / week

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from $48 / night

(5) 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  …see more

from $121 / night

$847 - $2324 / week

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from $121 / night

26

Villa accommodation in Arco da Calheta with swimming pool, golf nearby

Calheta / Arco da Calheta

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Maximum capacity for 8 person, possibility for more 3 person with camp beds4 bedroom typical Madeiran villa cottage in stone rocks with glass pool, big barbecue with table, modern full kitchen, 2 bathrooms, garage and big garden, 3 min to Calheta sand golden beach,  …see more

from $56 / night

$390 / week

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from $56 / night

16

Madeira / Calheta

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $107 / night

$749 / week

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from $107 / night

(2) Excellent 

25

Vacation villa with swimming pool in Arco da Calheta

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 do  …see more

from $177 / night

$1236 / week

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from $177 / night

35

Vacation cottage with golf nearby in Arco da Calheta

Calheta / Arco da Calheta

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
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 $44 / night

$307 / week

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from $44 / 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 $71 / night

$491 - $991 / week

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from $71 / night

20

Arco da Calheta Vacation villa accommodation

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
House with 3 bedrooms, seating for 6 people comfortably, close to the beach ...A mix of traditional and modern give a special touch to this House, built for comfort and sense of freedom outdoors. It is a house of about 400m2, which serve the needs of all types of cu  …see more

from $95 / night

$659 - $839 / week

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from $95 / night

(4) Excellent 

24

Vacation villa in Arco da Calheta

Calheta / Arco da Calheta

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • 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 $175 / night

$1225 - $1824 / week

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from $175 / 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  …see more

from $91 / night

$621 - $1718 / week

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from $91 / night

(1) Excellent 

28

Faja da Ovelha Vacation home accommodation

Calheta / Faja da Ovelha

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Private garden
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  …see more

from $38 / night

$246 - $396 / week

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from $38 / night

16

Vacation home in Estreito da Calheta

Calheta / Estreito da Calheta

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
We are located in Estreito da Calheta, where nature dominates green, allowing to enjoy panoramic views over Atlantic ocean. Designed to take full advantage of nature, combined with the comfort of an innovative and tasteful construction. We propose spaces decorated with  …see more

from $188 / night

$1311 / week

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from $188 / 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 $191 / night

$1337 - $2771 / week

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from $191 / 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 $91 / night

$637 - $1124 / week

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from $91 / night

(1) Excellent 

12

Vacation home in Estreito da Calheta

Calheta / Estreito da Calheta

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Beautifull and recently renovated stone house with two bedrooms both with sea view, one bathroom,fully equipped kitchen,garden area,BQ area,car park ,5 minutes from the yellow sand beach and with an excellent sun exposure. Supermarket and bar within a walking distance,s  …see more

from $65 / night

$450 / week

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from $65 / 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  …see more

from $121 / night

$847 - $2435 / week

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from $121 / 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  …see more

from $38 / night

$263 / week

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from $38 / 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 $296 / night

$824 - $3325 / week

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from $296 / 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  …see more

from $62 / night

$431 - $603 / week

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from $62 / night

(1) 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 $161 / night

$1124 - $1567 / week

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from $161 / night

(9) Very Good 

41

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

 …see more

from $86 / night

$899 - $1423 / week

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from $86 / night

24

Vacation home rental

Calheta / Arco da Calheta

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
A lovely two-bedroom cottage with garden overlooking rural views. Perfectly located in a quiet setting, but close enough to visit all this area has to offer. The well-equipped kitchen comes complete with granite worktops adding to the character. One of the bedrooms, lo  …see more

from $70 / night

$487 / week

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from $70 / night

67

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

4 4 1 night min

  • 4 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
The Naty & Chicos Apartament is a beautiful traditional Madeira cottage. Have 2 bedrooms at 1º floor with 2 double beds, 2 bathrooms, sitting-dinning areas and full equipped kitchen! Beautiful garden with direct and quiet private ocean blue direct views. A big  …see more

from $40 / night

$278 / week

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from $40 / night

(1) Very Good 

66

Calheta / Prazeres

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 6 mi
  • Swimming pool
  • Child friendly

 …see more

from $107 / night

$749 / week

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from $107 / night

(8) Excellent 

20

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 $70 / night

$487 / week

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from $70 / night