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Madalena Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Madalena vacation rentals

Deluxe Villa | Soundproofing, iron/ironing board, free WiFi, bed sheets
Pico Terrace

Villa in Madalena

Pico Terrace
3.0 star property
9.8 out of 10, Exceptional, (8)
"We had a good time in this comfortable place. "
Canada
Arianne
Pico Terrace
Outdoor pool
Aldeia dos Caldeirões

Villa in Madalena

Aldeia dos Caldeirões
3.0 star property
The price is ￥15,695
￥16,323 total
includes taxes & fees
Dec 12 - Dec 13
Aldeia dos Caldeirões
Exterior
Calm and rest combined with well-being with great views of the mountain and sea

Apartment in Madalena

Calm and rest combined with well-being with great views of the mountain and sea
9.4 out of 10, Exceptional, (6)
"Très bon accueil, grand appartement Très bien équipé avec tous les produits d'entretien disponibles. "
France
PATRICIA
Calm and rest combined with well-being with great views of the mountain and sea
Outdoor pool
Ocean View Pico

Vacation Home in Madalena

Ocean View Pico
10.0 out of 10, Exceptional, (6)
"The house was fantastic and Nico (the host) was very responsive, hospitable and warm. Nico made our stay very comfortable and came to the house in minutes any time there was a problem. We highly recommend staying at this property. "
United States
Shika S.
Ocean View Pico
Outdoor dining
Casa de Rosa, Pico Island, Vila da Madalena, Azores, Portugal - Free wifi

Vacation Home in Madalena

Casa de Rosa, Pico Island, Vila da Madalena, Azores, Portugal - Free wifi
9.2 out of 10, Wonderful, (13)
"Great location, and beautiful house!"
United States
Casey M.
Casa de Rosa, Pico Island, Vila da Madalena, Azores, Portugal - Free wifi
Aerial view
Atlantis Breeze

Cottage in Madalena

Atlantis Breeze
3.0 star property
Atlantis Breeze
Property grounds
Casa Baleia Laranja Ocean-Front

Villa in Madalena

Casa Baleia Laranja Ocean-Front
10.0 out of 10, Exceptional, (3)
"The location of the property was wonderful. We could hear the waves crashing throughout our stay. Thank you again "
United States
Sebastien B.
The price is ￥63,477
￥85,059 total
includes taxes & fees
Dec 25 - Dec 26
Casa Baleia Laranja Ocean-Front
TV, DVD player
Vacation Home "Retiro Dos Cabritos" with Sea View and Private Terrace

Vacation Home in São Mateus

Vacation Home "Retiro Dos Cabritos" with Sea View and Private Terrace
The price is ￥37,157
￥37,157 total
includes taxes & fees
Dec 18 - Dec 19
Vacation Home "Retiro Dos Cabritos" with Sea View and Private Terrace
Fridge, microwave, dishwasher, cookware/dishes/utensils
Large 2 bedroom apartment

Apartment in Açores

Large 2 bedroom apartment
6.8 out of 10, (3)
"A estadia coreu bem, no entanto notamos que os lençóis das camas são ásperos e que a limpeza não estava a 100%, nomeadamente armários e gavetas com pó e restos de baratas. Todos os dias tivemos de matar várias baratas."
Portugal
Luis A.
Large 2 bedroom apartment
Pool
CASA DA ESTRELA SIRIUS

Vacation Home in MADALENA DO PICO

CASA DA ESTRELA SIRIUS
CASA DA ESTRELA SIRIUS
Exterior
Baía da Barca

Aparthotel in Madalena

Baía da Barca
2.5 star property
Baía da Barca
Aerial view
Lofts Azul Pastel

Aparthotel in Horta

Lofts Azul Pastel
4.0 star property
9.8 out of 10, Exceptional, (33)
"Beautiful stay and wonderful staff!"
United States
Cathy
Lofts Azul Pastel
Exterior
Aldeia das Adegas

Apartment in Sao Roque do Pico

Aldeia das Adegas
4.0 star property
9.4 out of 10, Exceptional, (63)
"Diana is friendly and responsive with our requests. We stayed at one bedroom apartment. It feels like staying at home but in the paradise. "
United States
Raechung
The price is ￥17,533
￥18,235 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Aldeia das Adegas
Property grounds
Cliff-Top Ocean-Fronted Villa With Gardens And Private Pool

Villa in Silveira, Lajes do Pico

Cliff-Top Ocean-Fronted Villa With Gardens And Private Pool
9.8 out of 10, Exceptional, (49)
"We had such a relaxing stay at this beautiful home. My two kids loved the pool and the location next to the natural pools was amazing. Highly recommend!"
United States
Kris S.
Cliff-Top Ocean-Fronted Villa With Gardens And Private Pool
Microwave, oven, stovetop, dishwasher
Panoramic Ocean Views from your Private Varand

Vacation Home in São Roque do Pico

Panoramic Ocean Views from your Private Varand
The price is ￥22,520
￥28,527 total
includes taxes & fees
Dec 11 - Dec 12
Panoramic Ocean Views from your Private Varand
Adega da Atafona, 1 Bedroom, Ocean View | Terrace/patio
Adegas do Pico

Cottage in Sao Roque do Pico

Adegas do Pico
4.0 star property
9.0 out of 10, Wonderful, (38)
"Very nice rural property "
United States
Mario
Adegas do Pico
Smart TV, DVD player, books
AtlanticWindow - Modern House, Stunning View

Vacation Home in São Roque do Pico

AtlanticWindow - Modern House, Stunning View
10.0 out of 10, Exceptional, (49)
"The house was very comfortable for 4 adults and had everything needed for a great stay. The view is spectacular. Helena was very accommodating. I would recommend AtlanticWindow for anyone looking to stay on Pico for a few days. "
Portugal
Doyle B.
AtlanticWindow - Modern House, Stunning View
Outdoor pool
A Casa do Ouvidor

Villa in Sao Roque do Pico

A Casa do Ouvidor
4.0 star property
9.8 out of 10, Exceptional, (29)
"Asan was a great host. Quiet place, very roomy and clean, the view is amazing. Every thing was in place to enjoy a confortable stay. "
Canada
Sébastien
A Casa do Ouvidor
View from property
Porto Pim Bay

Aparthotel in Horta

Porto Pim Bay
9.6 out of 10, Exceptional, (31)
"Nice flat and Friendly staff. "
Germany
Soeren
Porto Pim Bay
Interior
Pike Cliffs - Amazing view to S. Jorge

Vacation Home in Prainha de Cima

Pike Cliffs - Amazing view to S. Jorge
9.6 out of 10, Exceptional, (8)
"We stayed at Pike Cliffs in July. The house is lovely and suitable for 4-6 people. We really like the views, and were able to reach Francisco when we got lost getting to the place. Thank you Francisco!"
Canada
A C.
Pike Cliffs - Amazing view to S. Jorge
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.
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Top Madalena Hotel Reviews

Pico TERRAMAR & SPA

Pico TERRAMAR & SPA

10/10 Excellent
"Staff were great. I arrived early from my flight & they quickly got my room ready so I could unoack & relax. Meal was excellent."
Deirdre Janine 1-night trip
Posted 2 weeks ago
Pico TERRAMAR & SPA

Find out more about Madalena

Search for holiday rentals in Madalena on Expedia! You can easily find your home rentals, villas, holiday apartments in Madalena using one of the methods below:

  • View our selection of featured holiday rentals in Madalena
  • Use the map to find apartments and other holiday homes in the Madalena neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Madalena while they last

Look no further and take a look at our great range of rental properties in Madalena!

Frequently asked questions

Can I find vacation rentals in Madalena?

Yes, we offer vacation rentals close to popular local attractions in Madalena, or you can select a more remote option if you're looking for relaxation. Madalena is known for its parks and wineries. Make sure you have time to check out the waterfront and museums during your trip.

What are some of the best vacation rentals that Madalena has to offer?

Casa de Rosa, Pico Island, Vila da Madalena, Azores, Portugal - Free wifi: This highly rated vacation home rental in Madalena is located in the mountains and has a balcony, a garden, and laundry facilities to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books. Another good choice for your trip to Madalena is Ocean View Pico.

How many vacation rentals are there in Madalena?

Choose from 13 Expedia vacation rentals in Madalena for a memorable vacation.

What can I see and do in Madalena?

Mount Pico and Pico Island Vineyard Culture are a couple of scenic spots to enjoy the outdoors, whereas Museu do Vinho is one of the cultural attractions. While here, Gruta das Torres and Azores Wine Company are other places worth a visit.

What are vacation rentals like in Madalena?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Madalena. Vacation rentals offer amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.