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 poolside dining area with a view of the ocean, featuring burgers and fries on the table.

1. 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 $117
CA $117 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
A stone building with a tiled roof, a staircase leading to a seating area with chairs, and lush greenery surrounding the property.

2. 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 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 $255
CA $284 total
includes taxes & fees
Oct 17 - Oct 18
Casa da Terra Alta
A white building with grey trim, a stone wall, and a small garden with various plants.

4. Silveira House

Silveira House
Lajes do Pico
The price is CA $72
CA $140 total
includes taxes & fees
Oct 26 - Oct 27
Silveira House
A covered outdoor seating area with a table and chairs, overlooking a scenic view of the sea and green landscape.

5. 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 stone building with a stone wall, a window, and a door leading to an interior with a cow-patterned wall.

6. 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 14 - Oct 15
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi
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 $280
CA $280 total
includes taxes & fees
Oct 20 - Oct 21
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
A stone wall with a wooden fence.

8. 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 $420
CA $546 total
includes taxes & fees
Oct 14 - Oct 15
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
A room with a wooden ceiling, a bed, a desk with a lamp, a fan, and a window.

9. 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 16 - Oct 17
Holiday Home 'Adega Pérola' with Wi-Fi
A stone building with a red door, green shutters, and a balcony.

10. 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 $471
CA $539 total
includes taxes & fees
Oct 14 - Oct 15
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.

11. 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 $350
CA $350 total
includes taxes & fees
Nov 1 - Nov 2
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.

12. 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 $720
CA $788 total
includes taxes & fees
Oct 14 - Oct 15
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi
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 $272
CA $330 total
includes taxes & fees
Nov 1 - Nov 2
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)
The price is CA $350
CA $412 total
includes taxes & fees
Oct 18 - Oct 19
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 $264 total
includes taxes & fees
Nov 2 - Nov 3
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. 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 $311
CA $354 total
includes taxes & fees
Nov 2 - Nov 3
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

18. 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 $204
CA $233 total
includes taxes & fees
Nov 2 - Nov 3
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
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 $386 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 $311
CA $349 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 3 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 $117
Highest Price
CA $788

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