A mountain with a lake in the foreground.

Pico Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Pico Island vacation homes

A stone building with a tiled roof, a staircase leading to a seating area with chairs, and lush greenery surrounding the property.

1. Casa do Laureano

Casa do Laureano
Santo Amaro
The price is CA $167
CA $196 total
includes taxes & fees
Oct 17 - Oct 18
Casa do Laureano
A poolside dining area with a view of the ocean, featuring burgers and fries on the table.

2. Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
Lajes do Pico
The price is CA $116
CA $116 total
includes taxes & fees
Nov 3 - Nov 4
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
A stone building with a wooden deck, a table, and chairs.

3. Casa da Terra Alta

Casa da Terra Alta
Santo Amaro
10.0 out of 10, Exceptional, (1 review)
"We had great stay, a fabulous place to sit and enjoy the view in the evening. The house was comfortable and had everything we needed. Bed linens and towels were of good quality, not always the case in some places we have stayed in. Erica was a lovely host; you could tell she cared very much for the house and garden. We would recommend Highland Homes to anyone going to Pico Island!"
Canada
Anonymous traveller
The price is CA $263
CA $291 total
includes taxes & fees
Oct 17 - Oct 18
Casa da Terra Alta
A stone building with a stone wall, a window, and a door leading to an interior with a cow-patterned wall.

4. Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi
Lajido
The price is CA $245
CA $245 total
includes taxes & fees
Oct 16 - Oct 17
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi
A white building with grey trim, a stone wall, and a small garden with various plants.

5. Silveira House

Silveira House
Lajes do Pico
The price is CA $72
CA $140 total
includes taxes & fees
Oct 29 - Oct 30
Silveira House
A covered outdoor seating area with a table and chairs, overlooking a scenic view of the sea and green landscape.

6. Pico Azores - Family house S. Jorge view

Pico Azores - Family house S. Jorge view
Ribeirinha
10.0 out of 10, Exceptional, (1 review)
"Nous étions 2 familles et avons passé une superbe semaine. Les chambres sont bien divisées et il y avait le nécessaire pour notre séjour. La maison est très propre et très belle."
United States
Amélie T.
The price is CA $201
CA $491 total
includes taxes & fees
Nov 1 - Nov 2
Pico Azores - Family house S. Jorge view
A rectangular pool with clear blue water, surrounded by a tiled deck.

7. Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
Ribeiras
The price is CA $279
CA $279 total
includes taxes & fees
Oct 25 - Oct 26
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
A room with a wooden ceiling, a bed, a desk with a lamp, a fan, and a window.

8. Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is CA $131
CA $238 total
includes taxes & fees
Oct 17 - Oct 18
Holiday Home 'Adega Pérola' with Wi-Fi
A stone building with a red door, green shutters, and a balcony.

9. Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
Pontas negras
7.0 out of 10, Good, (2 reviews)
"Nicley updated and clean but damp/musty smell. Location was good but required a drive to any attractions, restaurants, or markets. Balcony was nice but required access through the main bedroom. No communications on check-out procedures. Price was a bit high for what was offered."
United States
Eugene S.
The price is CA $470
CA $537 total
includes taxes & fees
Oct 23 - Oct 24
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
A hotel room with a bed, a view through a door, and a balcony.

10. Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
Engrade
10.0 out of 10, Exceptional, (1 review)
"Pros: The house was recently renovated, everything was nice and clean, very kind host, peaceful place with view of the ocean and vineyards"
United States
Anonymous traveller
The price is CA $349
CA $349 total
includes taxes & fees
Nov 10 - Nov 11
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
A modern living room with a wooden staircase, a sofa, a coffee table, and a dining area.

11. Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi
Pontas Negras
The price is CA $718
CA $786 total
includes taxes & fees
Oct 16 - Oct 17
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi
A stone wall with a wooden fence.

12. Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning

Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
Prainha
The price is CA $388
CA $514 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
A rocky shoreline with waves, a clear sky, and distant mountains.

13. Holiday Home 'Casa Praya' with Sea View, Private Terrace and Wi-Fi

Holiday Home 'Casa Praya' with Sea View, Private Terrace and Wi-Fi
Horta
The price is CA $271
CA $330 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Home 'Casa Praya' with Sea View, Private Terrace and Wi-Fi
A dining table with two plates, two wine glasses, and a vase with a plant.

14. Casa da Petra – Our Casa is your Casa

Casa da Petra – Our Casa is your Casa
Urzelina
The price is CA $663
CA $663 total
includes taxes & fees
Oct 19 - Oct 20
Casa da Petra – Our Casa is your Casa
A stone building with a window and shutters, surrounded by green hedges and a clear sky.

15. Holiday Home 'Da Boa Vista' with Sea View and Wi-Fi

Holiday Home 'Da Boa Vista' with Sea View and Wi-Fi
Pedro Miguel
8.0 out of 10, Very good, (3 reviews)
"Von den 4 Unterkünften, die wir in diesem Urlaub auf den Azoren hatten, ist dies die Einzige, die wir nicht empfehlen können. Als wir ankamen (Anfang Mai) waren die Temperaturen zwischen 11 und 17 Grad, mit wenigen sonnigen Abschnitten und dann höheren Temperaturen. Das Haus verfügt über keine Heizung, dementsprechend war die Temperatur im Inneren bei 16 Grad und über 80% Luftfeuchtigkeit. Die Wohnung war also kalt und klamm, in den Schränken und Kommoden riecht es modrig. Erst auf Nachfrage...
Germany
Bernd R.
The price is CA $349
CA $411 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Home 'Da Boa Vista' with Sea View and Wi-Fi
A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

16. Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
Calheta
The price is CA $226
CA $263 total
includes taxes & fees
Nov 15 - Nov 16
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

17. Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
São Jorge
The price is CA $203
CA $232 total
includes taxes & fees
Nov 2 - Nov 3
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

18. Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
São Jorge
10.0 out of 10, Exceptional, (1 review)
"The view from the property was spectacular! Lucas was extremely helpful and kind. A unique experience that has made us wanting to come back again for a longer stay."
United States
Kimberly
The price is CA $310
CA $354 total
includes taxes & fees
Nov 2 - Nov 3
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
A coastal landscape with a stone wall, a grassy area, and a view of the ocean and mountains.

19. Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
São Jorge
10.0 out of 10, Exceptional, (6 reviews)
"location, location, location plus the thoughtful design, adaptive reuse of structures, and the evident and abundant care of ownership and staff all added up to bliss for our group perhaps not for everyone, but the adventure of getting there and provisioning one’s stay can make for an even more satisfying stay."
United States
David B.
The price is CA $331
CA $387 total
includes taxes & fees
Nov 2 - Nov 3
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

20. Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
São Jorge
10.0 out of 10, Exceptional, (2 reviews)
"serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso."
Portugal
Pedro E.
The price is CA $310
CA $350 total
includes taxes & fees
Nov 2 - Nov 3
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
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 Pico Island Hotel Reviews

Porto Velho Boutique Lodge

Porto Velho Boutique Lodge

10/10 Excellent
"This place was amazing! It’s right by the water, with the ferry literally at your doorstep. Waking up each morning was great, especially with the waterfront views of Faial. They have coffee available 24/7 and pastries in the morning, plus a few local shops nearby for food, delicious may I add! I stayed in the basement and it was great. The place was very clean, had a kitchen with plates and dishes, and I absolutely loved the terrace. Yes, you can hear the church bells since the place is directly across from a church, and you can hear people if they’re loud upstairs, but that’s pretty normal for a basement. I’m not a light sleeper, and I slept like a baby here. The room did get a bit humid at night, but they had an AC unit, which was perfect. The location is central to everything in Madalena. The grocery store is about a 5-minute walk, and you’re within walking distance of pretty much anything you need. It’s also only about 10 minutes from the airport. The staff were incredibly kind and gave great recommendations for places to see. Entry and exit were easy, they had secure places for your bags in the room which is important to me. I cannot praise this place enough. If you need somewhere to stay in Madalena, I honestly wouldn’t recommend looking anywhere else. The location, the views, the staff, and the place itself were all perfect. I would absolutely stay here again!"
Tania 1-night trip
Posted 4 days ago
Porto Velho Boutique Lodge

Find out more about Pico Island

Pico Island Vacation Homes information

Number of reviews
15
Accommodation
130 Vacation Homes
Lowest Price
CA $116
Highest Price
CA $786

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