50 Best Vacation Rentals in Madeira Islands - Holiday Lettings - Cabins

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(20) Excellent 

48

Vacation villa in Madeira Islands

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 $239 / night

$1479 - $2814 / week

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from $239 / 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

$651 - $1363 / week

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from $93 / night

(2) Excellent 

24

Vacation cottage in Madeira Islands

Madeira / Sao Vicente

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Experience the Madeiran countryside and culture in this lovingly restored and delightful traditional stone cottage, snuggled in the small country village of Lamaceiros, yet close to the coast and sea. Located in the country village of Lameiros, 4,5 Km from the town of  …see more

from $38 / night

$260 - $661 / week

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from $38 / night

(6) Very Good 

20

Vacation cottage in Madeira Islands

Madeira / Estreito de Camara de Lobos

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 6 mi
  • Child friendly
  • Private garden
The picturesque Haybarn Cottage is set in a beautiful country estate in the sun-drenched hills west of Funchal. The cottage is set apart and has its own private garden with lovely views and is surrounded by mature trees. The ideal choice for those seeking a combination  …see more

from $32 / night

$223 - $446 / week

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from $32 / night

(11) Excellent 

18

Madeira / Arco de Sao Jorge

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

 …see more

from $53 / night

$371 / week

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from $53 / night

(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 $43 / night

$297 - $750 / week

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from $43 / night

23

Madeira / Porto da Cruz

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

 …see more

from $63 / night

$438 / week

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from $63 / night

(1) Excellent 

12

Madeira / Santa Cruz

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly

 …see more

from $27 / night

$181 - $425 / week

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from $27 / night

(6) Excellent 

28

Villa rental in Madeira Islands with swimming pool

Funchal / Sao Goncalo

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly
Superbly positioned above Funchal to benefit from the panoramic views of the town and ocean this beautifully furnished upmarket large villa provides a luxury experience for your holiday in Madeira. These views are always in display, from the living area, the front terra  …see more

from $136 / night

$950 - $2523 / week

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from $136 / night

(7) Excellent 

29

Madeira Islands Vacation apartment rental

Madeira / Machico

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Comfort Self Catering in the heart of Machico Old Town, sand beach 2 mn walk Modern apartment, located in historic center, overlooking the main avenue of the city of Machico and for this reason it was given the name of CASA DA AVENIDA. It consists of one double bedroom  …see more

from $41 / night

$276 - $509 / week

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from $41 / night

(23) Excellent 

20

Vacation apartment with shared pool in Madeira Islands

Funchal / Ajuda

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Suitable for children age 5+
This Funchal Madeira apartment is one-bed but can sleep up to four people if two comfortable foldaway beds (supplied) are used. The bed in the main bedroom has a very comfortable memory-foam mattress. The apartment has been furnished to a high standard and includes c  …see more

from $59 / night

$409 - $668 / week

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from $59 / 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

$846 - $2434 / week

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from $121 / night

(5) Very Good 

25

Vacation villa with swimming pool in Madeira Islands

Ponta Do Sol / Canhas

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
A lovely Villa with Heated Pool, in the sunny countryside close to the ocean. Set in a small tranquil complex of contemporary houses, the three bedroomed, modern and very well appointed. Casa de Sonho offers everything you could want from a tranquil holiday villa.Loca  …see more

from $218 / night

$742 - $1781 / week

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from $218 / night

(3) Excellent 

18

Calheta / Estreito da Calheta

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly

 …see more

from $69 / night

$483 / week

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from $69 / night

(1) Excellent 

30

Vacation home in Madeira Islands

Madeira / Ponta Do Sol

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
A veritable balcony over the ocean and the village of Ponta do Sol, with outstanding panoramic views, this sun kissed holiday home is set in a tranquil area and is perfect for those seeking peace and privacy. Very well furnished and comfortable, it has a large open-plan  …see more

from $53 / night

$371 - $995 / week

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from $53 / night

(21) Very Good 

33

Home rental in Madeira Islands

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 $38 / night

$260 - $297 / week

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from $38 / night

(7) Excellent 

38

Ponta Do Sol / Canhas

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly

 …see more

from $159 / night

$1113 / week

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from $159 / night

30

Madeira / Santa Cruz

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

 …see more

from $43 / night

$297 / week

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from $43 / night

(1) Very Good 

38

Madeira / Machico

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden

 …see more

from $43 / night

$292 - $329 / week

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from $43 / night

49

Madeira Islands Vacation villa rental

Madeira / Gaula

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Located on the hillside of Gaula, with superb views over the local countryside and out to sea. From the lounge terrace steps lead down to the heated pool area where the sea views can be best enjoyed. Behind the pool is a lovely garden area, immaculately maintained , pro  …see more

from $138 / night

$965 / week

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from $138 / night

(39) Excellent 

43

Penthouse rental in Madeira Islands

Madeira / Funchal

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Mansarda dos Aranhas is a boutique style, fully certified holiday penthouse. It has all the comfort and highest standards in equipment. This recently refurbished apartment is on the last two floors of a building (with lift) located in one of the oldest streets in Funcha  …see more

from $69 / night

$393 - $530 / week

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from $69 / night

(17) Excellent 

12

Vacation home in Madeira Islands

Madeira Islands / Porto Santo Island

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Discount for the last week in October. See our updated prices and have some family fun for the half-term! Direct flights from Lisbon to Porto Santo on Fridays and Sundays, so come for 10 days. Holiday Home on Porto Santo Island, Madeira Region, Portugal. Porto Santo  …see more

from $91 / night

$568 - $636 / week

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from $91 / night

(1) Excellent 

24

Vacation villa with shared pool in Madeira Islands

Madeira / Sao Jorge

4 12 4 nights min

  • 4 bedrooms
  • Sleeps 12
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Situated in a peaceful and solitary area with a pleasant climate all year round, it has a spectacularly panoramic view of the sea and mountains. Is a perfect starting point those who like walking or drive and discover Madeira Island. The house consists of four bedrooms  …see more

from $106 / night

$795 - $3021 / week

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from $106 / night

(2) Excellent 

19

Vacation home in Madeira Islands

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 $138 / night

$965 - $2115 / week

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from $138 / night

24

Villa rental in Campo de Baixo with golf nearby

Porto Santo Island / Campo de Baixo

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.07 mi
  • Child friendly
Villa 10 with a little garden, have DIRECT and PRIVATE ACCESS to the Beach Villa 10 is located in a private luxury community with doorman completely fenced. The beach “Praia do Ribeiro Salgado” have blue flag and is far 75 meters from the house, through a pr  …see more

from $53 / night

$371 - $1188 / week

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from $53 / night

(14) Excellent 

69

Madeira Islands Vacation apartment rental

Madeira / Funchal

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.7 mi
  • Child friendly
  • Pet friendly
A four-floor art house, with two bedrooms, including a residential living room, an airy veranda and a top floor art studio. A unique opportunity to become a citizen of the historical and artistic center of the town. Ideal for occupation by groups of between 2 to 6 peop  …see more

from $91 / night

$583 - $1023 / week

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from $91 / 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 $117 / night

$817 - $954 / week

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from $117 / night

(2) Excellent 

14

Madeira Islands Vacation apartment rental

Madeira / Funchal

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Ocean front apartment in Funchal city centre. In front of Funchal harbour. Located in the same building as the Cristiano Ronaldo museum.10 minutes walking distance from all major attractions in FunchalThis 1 room apartment with sofa bed feets confortably  …see more

from $64 / night

$446 / week

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from $64 / night

(1) Excellent 

22

Vacation studio in Madeira Islands

Madeira / Machico

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
I have 2 apartments can rent together or separately. My Studio offers a doble bed, kitchen and bathroom. Outdoor you find an area prepared for barbecue with a great Machico beach view. Amazing to relax in the end of after noon. Sand beach only 2 minutes by walk. Ideal  …see more

from $33 / night

$228 - $244 / week

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from $33 / night

(37) Very Good 

14

Vacation villa rental

Madeira / Funchal

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Villa Firdaus is centrally situated on the hillside above Funchal, close to amenities, making it ideal for exploring the island be it shopping, swimming in the sea, walking in the mountains or just relaxing at the villa.Relax in this tastefully decorated and wel  …see more

from $96 / night

$670 - $1121 / week

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from $96 / night

(3) Excellent 

25

Funchal Vacation villa rental

Funchal / Imaculado Coracao de Maria

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
With wonderful panoramic views that make you feel you are standing over the town and ocean, Casa da Pinheira II has been refurbished in a contemporary style to become a lovely holiday villa with heated pool. This newly refurbished 5-bedroom sister villa do Casa da Pinh  …see more

from $109 / night

$757 - $2718 / week

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from $109 / night

(1) Excellent 

20

Home rental in Madeira Islands

Madeira / Canico

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Ask about children
If you want to feel how it really is living as a local and having fun while staying in a great house, this place would be perfect for you and your family or friends. This house offers a great entrance, where you can just sit and have a glass of wine and read a book, or  …see more

from $32 / night

$212 / week

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from $32 / night

23

Vacation villa in Madeira Islands

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 $80 / night

$541 - $1756 / week

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from $80 / night

17

Madeira Islands Vacation villa rental

Ponta Do Sol / Canhas

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A two-stored detached house inserted in a 1000m2 plot and located in the rural area of Ponta do Sol municipality. It boasts fabulous ocean and mountain views.The roofed area is of 280m2. A large outdoors area includes a bungalow, a swimming pool (10x5m), a sunbathi  …see more

from $162 / night

$893 - $1408 / week

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from $162 / night

(24) Excellent 

28

Vacation apartment in Madeira Islands

Funchal / Old Town, Santa Maria Maior

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.27 mi
  • Child friendly
  • Car not necessary
Beautiful two bedroomed seafront apartment with superb view from the balcony towards Funchal city. Excellent location, close to the major road links to move to any point on the Madeira Island. Staying with us is the best choice because we are near a golf course, near th  …see more

from $91 / night

$631 - $705 / week

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from $91 / night

(1) Excellent 

14

Vacation apartment in Madeira Islands

Madeira / Estreito de Camara de Lobos

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Casa Paddock is set in a beautiful country estate in the sun-drenched hills west of Funchal. This two-bedroomed 1st floor property is set above the riding school and has superb views of the estate, countryside and ocean. The ideal choice for those seeking a combinatio  …see more

from $32 / night

$223 - $512 / week

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from $32 / night

(2) Very Good 

22

Vacation apartment in Funchal

Madeira / Funchal

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
Modern two bedroom, two bathroom and fully equipped apartment nestled in a popular shopping centre called Forum. Fully equipped kitchen, flat screen TV and wireless internet access. Fantastic views of the ocean. Located on the main strip within walking distance to Funch  …see more

from $55 / night

$361 / week

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from $55 / night

74

Vacation penthouse in Madeira Islands

Madeira / Ponta Delgada

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
A very cozy and modern penthouse with a fabulous view that can even fascinate locals. Its perfect to accommodate a couple and two children or two couples. Choose to take your breakfast at a lovely balcony table facing the green northeast coast; to cook your meals in a f  …see more

from $75 / night

$446 / week

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from $75 / night

37

Vacation villa in Madeira Islands

Madeira / Calheta

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 Swimm  …see more

from $170 / night

$1188 / week

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from $170 / night

(2) Excellent 

19

Vacation apartment 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 3 mi
  • Child friendly
MARISOL is a licensed and certified holiday residence (registernumbers 843/13 and 844/13 ) in Arco Da Calheta , a picturesque village situated on the south coast of Madeira Island, Portugal. It meets all the quality criteria imposed by the local authorities, recognizabl  …see more

from $67 / night

$467 - $838 / week

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from $67 / night