50 Best Vacation Rentals in Calheta - Holiday Lettings - Cabins

Close

View larger map

Also consider

Arco da Calheta
180 properties
Estreito da Calheta
54 properties
Prazeres
39 properties
Ponta do Pargo
31 properties
Faja da Ovelha
28 properties
Paul do Mar
19 properties
Jardim do Mar
11 properties

Calheta

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,369 Vacation rentals

22

Faja da Ovelha Vacation cottage rental

Calheta / Faja da Ovelha

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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, beautiful f …see more

from $73 / night

$490 - $1,332 / week

Book View

Responds fast!
avg. 10 minutes

from $73 / night

(8) 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 $160 / night

$1,118 - $1,462 / week

Book View

Responds fast!
avg. 3 hours 58 minutes

from $160 / night

27

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 $37 / night

$259 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from $37 / night

(22) 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 $111 / night

$770 - $1,687 / week

Book View

Responds fast!
avg. 1 hour 18 minutes

from $111 / night

(1) Excellent 

18

Vacation villa in Estreito da Calheta

Calheta / Estreito da Calheta

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in the sun-drenched hills above Calheta, an old barn has been transformed into this new contemporary modern and chic 3-bed air-conditioned villa, with everything you may want for a great family holiday. Built to high standards, and very well furnished in a modern st …see more

from $124 / night

$868 / week

Book View

Responds fast!
avg. 2 hours 59 minutes

from $124 / night

(2) Excellent 

15

Arco da Calheta Vacation apartment rental

Calheta / Arco da Calheta

1 2 6 nights min

  • 1 bedroom
  • Sleeps 2
  • 6 nights min
  • 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 area: …see more

from $64 / night

$447 / week

Book View

Responds fast!
avg. 14 minutes

from $64 / 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 $209 / night

$1,462 / week

Book View

from $209 / night

11

Faja da Ovelha Vacation home rental

Calheta / Faja da Ovelha

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $35 / night

$241 / week

Book View

from $35 / night

(1) Excellent 

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 $220 / night

$1,535 - $3,181 / week

Book View

from $220 / night

(2) Excellent 

19

Prazeres Vacation home accommodation

Calheta / Prazeres

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Private garden
Is a house where you can enjoy quietly of unique moments provided by the surrounding environment with all the comfort and security. «Leahouse» is a possessor of a pleasant green space surroundings where you can enjoy a distinct solar exposure. Surprise yourself with the …see more

from $43 / night

$301 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from $43 / 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 $44 / night

$304 / week

Book View

Responds fast!
avg. 3 hours 54 minutes

from $44 / night

(6) Excellent 

24

Vacation villa in Calheta

Madeira / Calheta

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
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

from $135 / night

$946 / week

Book View

Responds fast!
avg. 2 hours 59 minutes

from $135 / night

29

Villa rental in Calheta

Madeira / Calheta

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • 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 $62 / night

$430 - $602 / week

Book View

Responds fast!
avg. 14 minutes

from $62 / night

19

Vacation home in Estreito da Calheta

Calheta / Estreito da Calheta

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Pet friendly
The house is equipped with everything needed to enjoy a great stay in Madeira, is near the main sights of Calheta, the taken of the island, walks in nature, and above all agree with the stunning sound of Nature here one breathes the fresh air and offers security and pea …see more

from $40 / night

$258 - $516 / week

Book View

from $40 / night

(3) Excellent 

24

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

2 3 5 nights min

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min
  • Nearest beach 2 mi
  • Private garden
Very peace located modern apartment with 2 bedrooms; one with a double bed and other with a single bed - possibility to have an extra single bed. The area of the garden is nice and flowes and planted exotic plants. Was built in the year 2000, the accommodation on the gr …see more

from $65 / night

$451 / week

Book View

from $65 / night

(5) 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 $197 / night

$1,376 - $2,536 / week

Book View

from $197 / night

(11) Very Good 

Certificate of Excellence

32

Estreito da Calheta Vacation villa rental

Calheta / Estreito da Calheta

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • 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

Certificate of Excellence

from $84 / night

$588 - $1,127 / week

Book View

Responds fast!
avg. 2 hours 44 minutes

from $84 / 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. It has two doub …see more

from $84 / night

$588 - $980 / week

Book View

Responds fast!
avg. 1 hour 25 minutes

from $84 / night

(1) Excellent 

22

Jardim do Mar Vacation home rental

Calheta / Jardim do Mar

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden
House overlooking the Atlantic Ocean. Plenty of privacy, peace and quiet. Home feature, built with stone and wood. Ideal place for Zen moments. Has barbecue and all amenities. Have broad areas and always with plenty of privacy. This House represents the realization of …see more

from $47 / night

$323 / week

Book View

Responds fast!
avg. 3 hours 35 minutes

from $47 / night

(30) 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 $289 / night

$1,836 - $3,384 / week

Book View

Responds fast!
avg. 3 hours 52 minutes

from $289 / night

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 $43 / night

$301 / week

Book View

Responds fast!
avg. 3 hours 35 minutes

from $43 / night

29

Vacation home in Paul do Mar

Calheta / Paul do Mar

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
Location, location, location! Ocean Front Beach Villa in the sunniest warmest village in Madeira! The Villa is private and detached between banana fields in the National Park of Madeira. Sleeps 6 in 3 bedrooms all with Ocean Views! Master Bedroom with en suite ba …see more

from $87 / night

$603 - $810 / week

Book View

Responds fast!
avg. 2 hours 7 minutes

from $87 / night

24

Jardim do Mar Vacation villa rental

Calheta / Jardim do Mar

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
Villa with stunning sea views. Swimming pool heated with sunbeds. Villa Inside is very well equipped with modern furniture. Wifi is available and air conditioning. Accommodation: Inside: 1st floor Kitchen fully equipped Living room with sea view + bluetooth speake …see more

from $30 / night

$209 - $4,728 / week

Inquire View

from $30 / 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 $77 / night

$533 / week

Book View

from $77 / night

(1) Excellent 

10

Vacation condo in Estreito da Calheta

Calheta / Estreito da Calheta

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Ask about children
Beautiful view directly from 216 mtr. on the Atlantic Ocean. Lived much balcony area, double bedroom and bathroom on the first floor is on the ground floor. Fitted kitchen with everything you need for the holidays. Enjoy plenty of space in the living area, so the Madeir …see more

from $98 / night

$676 / week

Book View

from $98 / 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 $68 / night

$474 / week

Book View

Responds fast!
avg. 2 hours 51 minutes

from $68 / night

(3) Excellent 

11

Vacation home in Ponta do Pargo

Calheta / Ponta do Pargo

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
O nome da Casa do Pastor deve-se às suas origens, uma vez que este grande palheiro era utilizado pelos pastores para guardar os seus rebanhos e o respectivo alimento. A casa foi reconstruída, tendo mantido o seu traço original em Pedra e a sua decoração e design inspira …see more

from $269 / night

$1,883 / week

Book View

from $269 / night

(1) Very Good 

4

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Casa da Pedra is a traditional Madeiran house in the village of Arco da Calheta. The locals reckon that Arco da Calheta has the best micro-climate of all! And it’s a quiet location . The house has two twin bedded rooms, one with an en-suite bathroom. They have twin be …see more

from $209 / night

$779 - $784 / week

Book View

from $209 / night

12

Home rental in Ponta do Pargo

Calheta / Ponta do Pargo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
A Casa dos Pereiros foi reconstruída a partir de uma casa onde diversas famílias com tradições agrícolas viveram ao longo de várias gerações. A sua decoração ligou-se a um dos quatro elementos, o Fogo, caracterizando-se como simples e rústica. Como o próprio nome indica …see more

from $156 / night

$1,092 / week

Book View

from $156 / night

(1) Very Good 

45

Vacation home in Arco da Calheta

Calheta / Arco da Calheta

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 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 $74 / night

$516 - $1,479 / week

Book View

Responds fast!
avg. 3 hours 54 minutes

from $74 / night

34

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 $91 / night

$637 / week

Book View

from $91 / 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 $116 / night

$808 / week

Book View

from $116 / night

(15) Excellent 

Certificate of Excellence

44

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

Certificate of Excellence

from $123 / night

$860 / week

Book View

Responds fast!
avg. 2 hours 47 minutes

from $123 / night

(2) Very Good 

16

Vacation home 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
2 Bedrooms, 2 bathrooms, sleeps 4, pool, wireless Traditional Madeira Cottage is a traditional Madeiran house in the village of Arco da Calheta. The locals reckon that Arco da Calheta has the best micro-climate of all! Ans it's a quiet location . The hous …see more

from $112 / night

$783 / week

Book View

from $112 / night

(2) Excellent 

17

Estreito da Calheta Vacation villa rental

Calheta / Estreito da Calheta

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Beautifull modern House with 3 bedroom with modern finishes. Sea View,and beautiful sunsets. Green surrounding and panoramic view over Estreito da Calheta. Very good sun exposure.Casa da Pinheira sits on the hillside overlooking the pretty village of Estreito da Calheta …see more

from $62 / night

$430 / week

Book View

Responds fast!
avg. 3 hours 58 minutes

from $62 / 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 $197 / night

$1,376 / week

Book View

from $197 / night

(4) Excellent 

14

Arco da Calheta Vacation home rental

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
2 Bedroom house,two bathroom sleeps 4 in Arco da Calheta with beautiful Seaview. Spend unbelievable afternoons looking at the sunset from the balcony. You can do your meals on the terrace everyday Fully equipped Kitchen. Garden area. Breath taking view. Sunbathing area. …see more

from $74 / night

$516 / week

Book View

Responds fast!
avg. 3 hours 58 minutes

from $74 / night

27

Massapez Vacation apartment rental

Calheta / Massapez

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • 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 $43 / night

$301 / week

Book View

Responds fast!
avg. 3 hours 22 minutes

from $43 / night

(1) Excellent 

20

Vacation villa with swimming pool in Arco da Calheta

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
The village of field with high quality pool atop a seaside cliff. Stunning views of the Atlantic Ocean, to the South coast of Madeira Island and the green banana plantations. Intimate, bucolic, peaceful and relaxing. Ideal for holidays and rest. The only noise is the wa …see more

from $210 / night

$1,464 - $3,272 / week

Book View

from $210 / night

22

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 $72 / night

$499 / week

Book View

from $72 / night