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

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(6) 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 $124 / night

$868 - $2382 / week

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from $124 / 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 $66 / night

$457 - $685 / week

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from $66 / 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 $28 / night

$185 - $436 / week

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from $28 / 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 $39 / night

$267 - $305 / week

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from $39 / night

(38) 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 $97 / night

$675 - $1130 / week

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from $97 / night

32

Vacation villa in Madeira Islands

Madeira / Canico

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
This stunning villa has a garage and a private pool, the living area, kitchen and swimming pool. It is an incredibly spacious property. There are 3 bedrooms and 3 bathrooms, also table and chairs and it has doors straight out to the terrace and swimming pool. Large ope  …see more

from $153 / night

$1066 / week

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from $153 / 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 $44 / night

$305 - $769 / week

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from $44 / night

(7) 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 $33 / night

$229 - $457 / week

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from $33 / night

(18) 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 $93 / night

$582 - $653 / week

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from $93 / 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 $94 / night

$657 - $1374 / week

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from $94 / night

(2) Excellent 

12

Apartment rental in Madeira Islands

Madeira / Funchal

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 5 mi
  • Child friendly
Located in Funchal prime area, this recently renovated apartment has the perfect location. From here you can access the sea (150mt), the Naval Club and the beautiful Praia Formosa beach which is 500 mts. away. Madeira forum shopping center, Restaurants, supermarket, an  …see more

from $49 / night

$348 - $455 / week

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from $49 / night

27

Calheta / Faja da Ovelha

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Pet friendly

 …see more

from $46 / night

$320 - $419 / week

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from $46 / 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 $124 / night

$868 - $2496 / week

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from $124 / 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 $98 / night

$680 - $1800 / week

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from $98 / night

32

Calheta / Faja da Ovelha

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from $64 / night

$442 - $685 / week

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from $64 / 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 $39 / night

$267 / week

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from $39 / night

(2) Excellent 

20

Madeira Islands Vacation studio rental

Madeira / Funchal

Studio 2 4 nights min

  • Studio
  • Sleeps 2
  • 4 nights min
OCEAN DREAM -2 Looking for a relaxing and quiet place to stay in Madeira? This is the ideal place for you. Here you will find one private suite composed of: - Bedroom for 2 with a double bed. - Bathroom. - Lounge with TV and Internet where you can also have the mea  …see more

from $33 / night

$229 / week

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from $33 / night

(5) Excellent 

21

Apartment rental in Funchal with swimming pool

Funchal / Ajuda

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
BRIGHT SEAFRONT APARTMENT IN FUNCHAL WITH BALCONY AND PRIVATE POOLComfortable well equipped one bedroom apartment within a secure condominium with a large outdoor pool, sun-deck and guest lounge in the hotel zone on the west of Funchal.The apartment  …see more

from $48 / night

$335 - $381 / week

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from $48 / night

(7) Very Good 

46

Madeira / Porto da Cruz

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden

 …see more

from $44 / night

$294 - $370 / week

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from $44 / 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 $93 / night

$647 - $1142 / week

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from $93 / night

(6) Excellent 

18

Vacation apartment rental

Canico / Reis Magos

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
Situated in the stunning locale of Canico de Baixo the apartment is 10min drive from the airport and 10min from the City of Funchal. Overlooking the beach of Reis Magos it offers amazing views out to sea and of the nearby 'desertas' islands in a very tranquil  …see more

from $54 / night

$388 - $400 / week

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from $54 / night

(1) Excellent 

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 $77 / night

$533 / week

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from $77 / 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 $39 / night

$267 - $678 / week

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from $39 / night

(12) Excellent 

28

Madeira Islands Vacation bungalow rental

Funchal / Sao Roque, Madeira

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
With an incredible view of the Atlantic and the city of Funchal, this typical Madeira house was restored by a renowned Portuguese architect in 2008, . Integrated in a 1300m2 property, very quiet, offers to guests a shared lush garden of tropical flowers, 120m2 balcon  …see more

from $74 / night

$571 - $754 / week

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from $74 / 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 $120 / night

$837 - $2787 / week

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from $120 / night

(3) Very Good 

24

Vacation apartment in Madeira Islands

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 $39 / night

$267 / week

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from $39 / night

(38) Excellent 

54

Vacation apartment rental

Madeira / Funchal

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 mi
  • Car not necessary
  • Private garden
Located just a few minutes walk from many of Funchal's most popular "must see places" you are living in the real city not the hotel tourist zone located several miles away from the city centre. This new luxury attic conversion has breathtaking views o  …see more

from $60 / night

$373 - $548 / week

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from $60 / 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 $55 / night

$381 / week

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from $55 / 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 $34 / night

$234 - $250 / week

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from $34 / night

20

Calheta / Arco da Calheta

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $164 / night

$1142 - $2283 / week

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from $164 / night

(2) Very Good 

22

Funchal Vacation apartment rental

Madeira / Funchal

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Child friendly
A new and elegant apartment, self-sufficient with a prime location in the city ( "Old Town"). In the first line of the sea with a fantastic view of the city and the Sea You can relax and enjoy great sunbathing either in the garden or on the beach just in front  …see more

from $42 / night

$272 - $310 / week

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from $42 / night

(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 $245 / night

$1517 - $2886 / week

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from $245 / night

(7) Excellent 

22

Madeira Islands 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
  • 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 $74 / night

$522 - $898 / week

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from $74 / night

(4) Excellent 

14

Madeira / Machico

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Private garden

 …see more

from $71 / night

$495 / week

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from $71 / night

18

Vacation apartment in Madeira Islands

Madeira / Machico

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
I have 2 apartments can rent together or separately. My Apartment offers a bedroom with a double bed, kitchen and bathroom. In the living room we have a sofa bed. Outdoor you find an area prepared for barbecue with a great Machico beach view. Amazing to relax in the  …see more

from $36 / night

$250 - $383 / week

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from $36 / 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 $44 / night

$305 / week

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from $44 / night

37

Madeira / Ribeira Brava

3 7 7 nights min

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

 …see more

from $75 / night

$598 - $1740 / week

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from $75 / night

(15) Excellent 

34

Madeira Islands Vacation villa rental

Madeira / Calheta

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 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 $55 / night

$381 - $740 / week

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from $55 / night

40

Madeira / Funchal

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

 …see more

from $79 / night

$548 / week

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from $79 / night

(4) Excellent 

22

Madeira Islands / Porto Santo Island

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation

 …see more

from $66 / night

$457 - $685 / week

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from $66 / night

1