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

Vacation Homes in Madeira Region

Compare and save
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Top Cities in Madeira Region

Our top choices for Madeira Region vacation homes

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

House on the island of flowers between sky and sea. EXCEPTIONAL views
Ribeira Brava
10.0 out of 10, Exceptional, (149 reviews)
"The host was super helpful even met us at the property to go over any questions we may have had. Kitchen was very well equipped, and even recommended a personal chef that was fantastic! Pool was very clean and a great end to the day after touring the island. Would not hesitate to stay here again."
United States
Annette L.
House on the island of flowers between sky and sea. EXCEPTIONAL views

2. House / Villa - Arco da Calheta

House / Villa - Arco da Calheta
Arco da Calheta
10.0 out of 10, Exceptional, (81 reviews)
"Good weatherBest Sightseeing Perfekt Holiday House "
Germany
Dietmar M.
House / Villa - Arco da Calheta

3. Casas da Levada

Casas da Levada
Calheta
9.8 out of 10, Exceptional, (22 reviews)
"Just the most tranquil, and wonderful stay. "
United Kingdom
Jin-Ah
The price is AED 1,105
AED 1,166 total
includes taxes & fees
4 Sep - 5 Sep
Casas da Levada

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

A peaceful, relaxing place with privileged view of the sea.
Tabua
9.2 out of 10, Wonderful, (17 reviews)
"The location is great! Only a 20 minute drive outside of Funchal, perfect to still head into the city for dinner or exploring but far enough away to avoid the noise and busyness. Very close to a couple beaches and amazing views from the patios for breakfast or afternoon drinks! The only thing to note is no wifi- so be prepared to purchase a large eSIM."
Canada
Courtney
A peaceful, relaxing place with privileged view of the sea.

5. ANGEL'S SUNSET T2 ESTRITO DA CALHETA

ANGEL'S SUNSET T2 ESTRITO DA CALHETA
Estreito da Calheta
10.0 out of 10, Exceptional, (1 review)
"Wir haben uns sehr wohl gefühlt und waren vom Service nach einer Woche sehr positiv beeindruckt."
Germany
Bettina S.
ANGEL'S SUNSET T2 ESTRITO DA CALHETA

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

Fortress Home I - In the historical center of Funchal
Sao Pedro
9.2 out of 10, Wonderful, (93 reviews)
"Very nice little apartment with breathtaking view from the balcony."
Canada
Maria T.
Fortress Home I - In the historical center of Funchal

7. House / Villa - FunchalHouse with character

House / Villa - FunchalHouse with character
Sao Pedro
9.0 out of 10, Wonderful, (111 reviews)
"Great place to stay. I love Madeira and thanks for your help for the smooth check-in at 2am."
United States
Cheuk Hin Sherman
House / Villa - FunchalHouse with character

8. Casa Gama Ideal Para Descansar

Casa Gama Ideal Para Descansar
Ribeira da Janela
8.0 out of 10, Very Good, (4 reviews)
"Great stay"
Canada
Gina
The price is AED 345
AED 432 total
includes taxes & fees
8 Sep - 9 Sep
Casa Gama Ideal Para Descansar

9. Villa Carpe Diem by Your Madeira Rentals

Villa Carpe Diem by Your Madeira Rentals
Estreito da Calheta
9.8 out of 10, Exceptional, (8 reviews)
"Great family villa. Fantastic facilities and views overlooking the sea. Spacious and well maintained accommodation and everything that we needed was provided. Worth mentioning the drive to the property entrance is quite steep but manageable."
United Kingdom
Louise H.
Villa Carpe Diem by Your Madeira Rentals

10. Casa Mozart I

Casa Mozart I
Estreito da Calheta
10.0 out of 10, Exceptional, (1 review)
"Nous avons passé un excellent séjour au sein du logement Casa Mozart I.Très bon emplacement, une vue magnifique et la propreté du logement.Merci encore."
United States
SOLENN L.
The price is AED 826
AED 1,587 total
includes taxes & fees
18 Sep - 19 Sep
Casa Mozart I

11. Nates House – Two-bedroom house with garden

Nates House – Two-bedroom house with garden
São Vicente
8.8 out of 10, Excellent, (3 reviews)
"Beautiful, quiet location."
United States
MIke W.
The price is AED 1,604
AED 2,142 total
includes taxes & fees
26 Sep - 27 Sep
Nates House – Two-bedroom house with garden

12. The North Paradise - Porto Moniz

The North Paradise - Porto Moniz
Ribeira da Janela
9.0 out of 10, Wonderful, (2 reviews)
"This beautiful guest house in Porto Moniz was more than perfect. Just minutes to get to the beach and a short drive to go hike levadas we were thrilled. In a quiet little neighbourhood yet close to what we needed. We had a car so was very easy to get to but there was a busy stop just steps away to accommodate guests using transit."
Canada
hammer k.
The North Paradise - Porto Moniz

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

Casa Félix, Calheta: Villa with unique view! Private Pool!
Madeira
10.0 out of 10, Exceptional, (145 reviews)
"Beautiful villa"
United Kingdom
Ian T.
Casa Félix, Calheta: Villa with unique view! Private Pool!

14. Villa Tomito, Arco da Calheta

Villa Tomito, Arco da Calheta
Arco da Calheta
9.4 out of 10, Exceptional, (45 reviews)
"We had a great time at a great place"
Netherlands
Frank P.
Villa Tomito, Arco da Calheta

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

House T2 with excellent views, located in the historical center of Funchal.
Sao Pedro
9.8 out of 10, Exceptional, (136 reviews)
"Hugo was friendly, funny and helpful Helped with our taxi to and from the airport too (Taxi Driver Joao was great) Great location for pretty much everything especially the Museums on the way down the hill to the harbour Great stay "
United States
Alan C.
House T2 with excellent views, located in the historical center of Funchal.

16. SUN AND SUN HOUSE

SUN AND SUN HOUSE
Arco da Calheta
10.0 out of 10, Exceptional, (27 reviews)
"I just enjoy my stay."
United States
Aleksej P.
SUN AND SUN HOUSE

17. Fortress Home II - In the historic center of Funchal

Fortress Home II - In the historic center of Funchal
Sao Pedro
9.4 out of 10, Exceptional, (117 reviews)
"It was close to the center and the marine. The apartment was excellent, with a great view. The only disadventage was the narrow street and the garage, because it was hard to park there, but 100m downhill was a cheap car park, so you can park there. We enjoyed our stay a lot. It was wonderful."
United Kingdom
Aneta P.
Fortress Home II - In the historic center of Funchal

18. Casa ZÈ, Tranquility, a Refuge in Arco da Calheta

Casa ZÈ, Tranquility, a Refuge in Arco da Calheta
Arco da Calheta
8.8 out of 10, Excellent, (8 reviews)
"Apartment superficially seems nice. Good kitchen - grill available. However: Definately not 200SQm. Upper bathroom smelly all the time because of drain, Sink could not be used because water was not flowing down. Porch: 10-20 flies at all times outside (still standing water in drain directly next to porch) - could not relax outside. Cushions were missing, after I asked they were in the sleeping room. Bathroom (downstairs): one of the windows could not be closed. Kitchen: Ants are welcomed guests...
Germany
Pascal K.
Casa ZÈ, Tranquility, a Refuge in Arco da Calheta

19. Casa Strelitzia by An Island Apart

Casa Strelitzia by An Island Apart
4.0 star property
Funchal
6.0 out of 10, (3 reviews)
"A great apartment on the edge of the old town. Fab views of the sea and of the local area - great for people watching. Good size living / kitchen area with well appointed cooking area. Full sized fridge freezer which is always a bonus. Bedroom at the back with a small rooflight window - no aircon - but a decent fan in both areas. Walk in bathroom/ shower was without a window and limited mechanical extraction - so had a v damp smell - a design fault - but had to keep that door closed. But the...
United Kingdom
Paul
The price is AED 1,986
AED 2,337 total
includes taxes & fees
5 Sep - 6 Sep
Casa Strelitzia by An Island Apart

20. With pool and barbecue - Villa Roque

With pool and barbecue - Villa Roque
Ponta do Pargo
8.0 out of 10, Very Good, (1 review)
"La villa était agréable et propre, un peu isolée, mais très calme. Seul reproche il manquait quelques équipements et la piscine était un peu fraîche, mais nous avons passé un très agréable séjour, et l'hôte a répondu à notre sollicitation de façon agréable et professionnelle."
United States
Stephane P.
The price is AED 1,856
AED 2,933 total
includes taxes & fees
15 Sep - 16 Sep
With pool and barbecue - Villa Roque
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Madeira Region Hotel Reviews

Explore a world of travel with Expedia