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

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(35) Excellent 

43

Penthouse rental in Madeira Islands

Madeira / Funchal

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • 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 $67 / night

$379 - $534 / week

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from $67 / 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 $43 / night

$299 - $673 / week

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from $43 / night

(5) Excellent 

20

Vacation cottage in Madeira Islands

Madeira / Estreito de Camara de Lobos

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • 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

$225 - $449 / week

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from $33 / night

Featured properties

(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 $92 / night

$625 - $1729 / week

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from $92 / 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

$182 - $428 / week

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from $27 / 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 $121 / night

$845 / week

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from $121 / night

(3) Excellent 

23

Madeira / Canical

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly

 …see more

from $49 / night

$257 / week

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from $49 / night

(6) Excellent 

30

Vacation home in Madeira Islands

Madeira / Santa Cruz

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
The house, registed as "1999/Alojamento Local", offers spacious accommodation and is excellently furnished to a contemporary standard. The 1st floor holds 3 bedrooms fully furnished and accommodates 6 people. There are 2 bathrooms. The master bedroom has an en  …see more

from $62 / night

$434 / week

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from $62 / night

(8) Excellent 

13

Vacation studio in Madeira Islands

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

(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 $219 / night

$748 - $1793 / week

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from $219 / 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

$299 - $755 / week

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from $43 / night

(5) Excellent 

20

Madeira / Porto da Cruz

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from $49 / night

$331 - $780 / week

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from $49 / night

20

Vacation apartment in Madeira Islands

Madeira / Funchal

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Located in Funchal next to the beach Cavacas dock in front of the Sea A very spacious apartment (160 m2) located on the top floor with large terrace. No car needed as you can walk to the beaches: Cavacas dock, Formosa Beach, Punta Gorda, Lido Beach, Club Naval ... All s  …see more

from $75 / night

$491 - $830 / week

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from $75 / night

(10) Very Good 

26

Vacation home rental

Madeira / Porto Moniz

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
A 19th century building, restored and adapted for holidays, which for its wonderful situation, based on an islet off the coast where we only came across through a wooden bridge, served as a warehouse for wine casks, which were afterwards transported by sea in a time whe  …see more

from $161 / night

$801 - $908 / week

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from $161 / night

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 $33 / night

$214 - $321 / week

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from $33 / night

19

Bungalow rental in Garajau with swimming pool

Madeira / Garajau

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Private garden
Bungalow that belongs to a private Villa with swimming-pool and amazing views over the ocean. This bungalow is surrounded by a big garden and a private swimming-pool.Perfect for a romantic get-away.The guests enter the Villa thru a private gate and h  …see more

from $75 / night

$523 / week

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from $75 / night

(11) Excellent 

27

Madeira Islands Vacation bungalow rental

Funchal / Sao Roque, Madeira

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • 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 $65 / night

$486 - $830 / week

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from $65 / night

(2) Excellent 

24

Vacation villa rental

Madeira / Funchal

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
A newly refurbished villa with a lovely holiday feel, ideal for families or for exploring Madeira, very close to facilities. Just refurbished, this lovely 5-bed villa has a great holiday feel and being located in a quite residential area, close to all facilities and t  …see more

from $106 / night

$740 - $3063 / week

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from $106 / night

(2) Very Good 

11

Villa rental in Madeira Islands

Madeira / Ponta Do Sol

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
This luxury villa with a heasted swimming pool, has outstanding views of the ocean and mountains and is situated in a quiet area in Ponta do Sol having the warmest climate in the south west of Madeira Island. It has a heated swimming pool and a large terrace for a relax  …see more

from $119 / night

$829 - $1244 / week

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from $119 / night

19

Madeira / Ponta Do Sol

2 4 4 nights min

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

 …see more

from $54 / night

$374 / week

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from $54 / night

9

Home rental in Gaula

Madeira / Gaula

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Spacious two-story modern house positioned in a peaceful village of Gaula, Set amid established gardens, the dual level layout is ideal for entertaining with a choice of living areas and a superb terrace capturing views over Atlantic Ocean and Desertas Islands. Bright  …see more

from $54 / night

$321 - $395 / week

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from $54 / night

(19) 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 $241 / night

$1489 - $2834 / week

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from $241 / night

(2) Excellent 

32

Vacation villa in Garajau

Madeira / Garajau

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Spectacular ocean front Villa, occupying one of the finest ocean front positions, with sensational 180º far reaching views, private heated swimming pool, garden, sea view terraces, games room, air conditioning in all bedrooms, two wood burning fires, for cooler winter  …see more

from $164 / night

$1146 - $2080 / week

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from $164 / 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 $89 / night

$621 / week

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from $89 / 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

$389 / week

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from $56 / 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

$225 - $561 / week

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from $33 / 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 $42 / night

$292 - $1002 / week

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from $42 / night

(7) Excellent 

21

Sao Martinho Vacation apartment rental

Madeira / Sao Martinho

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Apartamento com 2 suites, sala comum e cozinha, é perfeito para férias na Madeira. Num condomínio sossegado com piscina e jardim, está 5 minutos da zona comercial de lojas,restaurantes, centros de turismo.O centro da cidade está a 15 minutos a pé.Excellent 2 b  …see more

from $89 / night

$617 - $942 / week

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from $89 / night

(18) Excellent 

24

Vacation apartment rental

Madeira / Funchal

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Car not necessary
Located on the top floor of the buiding enjoys a huge balcony outside with a fantastic sea view. Enjoying your meals outside, unforgettable sunsets or reading a book at the outdoor jacuzzi, are only a few things that you can enjoy at this location. Cristal Studio is an  …see more

from $70 / night

$486 - $1046 / week

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from $70 / night

(34) 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 $49 / night

$321 - $587 / week

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from $49 / night

(5) Excellent 

29

Vacation home in Funchal

Madeira / Funchal

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Private garden
This traditional Quinta in Funchal offers one well equipped and comfortable apartment, enjoying a fantastic outside area with beautiful blooming gardens.The view over Funchal city, sea and harbor offers a unique scennary and the total privacy of the place assures yo  …see more

from $59 / night

$454 - $934 / week

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from $59 / night

10

Madeira / Ponta Do Sol

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 3 mi
  • Child friendly
  • Air conditioning

 …see more

from $54 / night

$374 / week

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from $54 / 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

$481 - $1072 / week

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from $70 / 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

(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 $107 / night

$801 - $3042 / week

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from $107 / night

(36) Excellent 

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 $98 / night

$686 - $1149 / week

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from $98 / night

(9) Very Good 

25

Apartment rental in Madeira Islands with shared pool

Funchal / Praia Formosa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool
This beach waterfront luxury private apartment with stunning panoramic views of the Atlantic is located on the 4th floor (2 lifts are available) of 4* resort Pestana Gardens, in the west Funchal, Lido area, on the beach Praia Formosa with direct access to the ocean  …see more

from $75 / night

$481 - $555 / week

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from $75 / night

(1) Very Good 

15

Madeira / Machico

1 2 Min stay varies

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

 …see more

from $38 / night

$264 - $377 / week

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from $38 / 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 $139 / night

$972 - $2130 / week

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from $139 / 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