Top Vacation Homes in Madeira Region in 2026

A coastal town with terracotta-roofed buildings, a prominent church, and a cliff overlooking the sea.

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Top Cities in Madeira Region

A densely packed urban area with a mix of colorful buildings, including a prominent white church with a bell tower.

A coastal resort with a pool, lounge chairs, and a view of the ocean.

Our top choices for Madeira Region vacation homes

A poolside view with a clear ocean view, a pool, and surrounding greenery.

1. House on the island of flowers between sky and sea. EXCEPTIONAL views

Ribeira Brava

Annette L.

A clear blue pool with a view of the ocean.

2. Casas da Levada

Calheta

Jin-Ah

AED 1,076 total

includes taxes & fees

20 Oct - 21 Oct

A modern living room with a white sofa, a flat-screen TV, and a bookshelf.

3. ANGEL'S SUNSET T2 ESTRITO DA CALHETA

Estreito da Calheta

"Had mostly everything that we needed. Clean and comfortable and with good facilities including designated parking.The only things I would like to see added:1. A kettle - us Brits like a cup of tea and some of us even like instant coffee.2. Fans for the bedrooms. As they don't have windows it can get stuffy and hot overnight.Our host, Elisabete, was wonderful. Gave us some welcome gifts and advice on where to go and what to do.Be aware that this is a set of 4 apartments that share the outdoor...

Jim M.

A living room with a sectional sofa, a flat-screen TV, a decorative wall piece, and a large window with curtains.

4. Eva's House

Funchal

A stone building with a red window, surrounded by palm trees and potted plants.

5. Relax in the middle of nature!!!

Arco da Calheta

Julia S.

A hotel room with a bed, a balcony, and a view of the sea.

6. House T2 with excellent views, located in the historical center of Funchal.

Sao Pedro

Alan C.

A beachside sign for Praia da Calheta, with sun loungers and umbrellas in the background.

7. Villa Santos, spacious, sleeps up to 8 , relaxed area, with an amazing sea view

Lombo Do Doutor

Zvonimir T.

A balcony with a table, chairs, a bottle of wine, and a red umbrella.

8. Fortress Home I - In the historical center of Funchal

Sao Pedro

"What a lovely stay we had!The place is located perfectly up a slight hill (easy walk from the town) giving you an amazing view of Funchal. House was clean and had all the amenities we needed including pots and pans, there is no air conditioning so it’s worth keeping the window open at night and this was okay for us The parking spot is tight, but very convenient and a great additional amenity to a lovely home"

Ben N.

A table set for breakfast with a view of the sea, outdoor chairs, and a pergola with flowers.

9. A peaceful, relaxing place with privileged view of the sea.

Tabua

Courtney

A coastal view with a balcony railing, a clear sky, and a distant town along the coastline.

10. Casa Gama Ideal Para Descansar

Ribeira da Janela

Gina

AED 419 total

includes taxes & fees

8 Oct - 9 Oct

A swimming pool with lounge chairs and an umbrella, surrounded by a tiled deck and a view of the landscape.

11. Villa Carpe Diem by Your Madeira Rentals

Estreito da Calheta

Louise H.

A patio with a view of the ocean, a mountain, and a fence with vegetation.

12. Nates House – Two-bedroom house with garden

São Vicente

MIke W.

AED 1,720 total

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a sofa, a dining table with chairs, a TV mounted on the wall, and a large window.

13. The North Paradise - Porto Moniz

Ribeira da Janela

hammer k.

A house with a tiled roof, a stone wall, and a white fence.

14. House 'Casa da Santa Maria Madalena'

Santa Maria Madalena

Serge B.

AED 929 total

includes taxes & fees

6 Oct - 7 Oct

A table with a fruit platter and two glasses of red wine, overlooking a calm body of water.

15. Casa Félix, Calheta: Villa with unique view! Private Pool!

Madeira

Ian T.

A coastal town with a curved promenade, a sandy beach, and a marina.

16. House / Villa - Arco da Calheta

Arco da Calheta

Dietmar M.

A balcony with a view of the sea and a distant village.

17. Villa Tomito, Arco da Calheta

Arco da Calheta

Frank P.

A swimming pool with a wooden deck, surrounded by lush greenery and a stone building with a red roof.

18. Quinta do Rosário Madeira traditional house

São Vicente

Thierry S.

A modern living room with a sofa, dining table, and kitchen in the background.

19. Caminho da Achada Apartment

Sao Pedro

Abdalla

A spacious living room with wooden flooring, a flat-screen TV, and large windows offering a view of the outdoors.

20. Machico View

Machico

"Maison toute équipée située sur une colline venteuse en bout de piste de l'aéroport (heureusement ce n'est pas le trafic de Roissy ou Heathrow). Toute les commodités sont là mais il ne faut pas être regardant sur les finitions et la qualité des articles fournis. Le matelas était neuf mais le sommier avait des lattes cassées. La télé avait une image très mauvaise. Le propriétaire exige 120 euros plus une TVA pour le ménage de la maison à faire en fin de séjour alors que la propreté laissait à...

marc

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Top Madeira Region Hotel Reviews

Hyatt Ziva Madeira

10/10 Excellent

"hotel was great from start to finish"

Calheta Beach - All Inclusive

10/10 Excellent

"Staff were very friendly! Entertainment and food were fabulous. Pool spotless, great to see the manager being there on the complex walking around observing. The bar staff and waiters/waitresses were charming and nothing too much for them. With the facilities, we were disappointed on first day to have no aircon in our room, heard others had same problem with this. We were moved to different room same day but it meant we lost time unpacking and packing again. Overall the stay was so lovely and we would recommend this hotel. We certainly will be returning."

Reid's Palace, A Belmond Hotel, Madeira

10/10 Excellent

"Reid’s is a beautiful property with multiple pools and diving access to the ocean. Our stay involved changing rooms ( not the hotels fault), and not all rooms are the same. The first room had a walk in shower but the second room had a very slippery tub shower. There was construction going on during our stay that made for noisy afternoons. The food was really good and there are multiple restaurants, however, I would reserve a table in advance of your stay to guarantee your spot at dinner. The service was exceptional."

Vacation Homes in Madeira Region

Change your mind

Treat yourself

Be picky

Check prices for these dates

Top Cities in Madeira Region

Funchal

Ponta do Sol

Our top choices for Madeira Region vacation homes

1. House on the island of flowers between sky and sea. EXCEPTIONAL views

2. Casas da Levada

3. ANGEL'S SUNSET T2 ESTRITO DA CALHETA

4. Eva's House

5. Relax in the middle of nature!!!

6. House T2 with excellent views, located in the historical center of Funchal.

7. Villa Santos, spacious, sleeps up to 8 , relaxed area, with an amazing sea view

8. Fortress Home I - In the historical center of Funchal

9. A peaceful, relaxing place with privileged view of the sea.

10. Casa Gama Ideal Para Descansar

11. Villa Carpe Diem by Your Madeira Rentals

12. Nates House – Two-bedroom house with garden

13. The North Paradise - Porto Moniz

14. House 'Casa da Santa Maria Madalena'

15. Casa Félix, Calheta: Villa with unique view! Private Pool!

16. House / Villa - Arco da Calheta

17. Villa Tomito, Arco da Calheta

18. Quinta do Rosário Madeira traditional house

19. Caminho da Achada Apartment

20. Machico View

Find vacation rentals that suit your style

Top Madeira Region Hotel Reviews

Hyatt Ziva Madeira

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