Pico Island Vacation Rentals

  • 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

Our top choices for Pico Island vacation rentals

Aldeia das Adegas

Aldeia das Adegas
4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (64 reviews)
"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 CA $155
CA $162 total
includes taxes & fees
Feb 22 - Feb 23
Aldeia das Adegas

Aldeia dos Caldeirões

Aldeia dos Caldeirões
3.5 star property
Madalena
The price is CA $150
CA $156 total
includes taxes & fees
Feb 10 - Feb 11
Aldeia dos Caldeirões

Casa dos Felicias

Casa dos Felicias
São Roque do Pico
10.0 out of 10, Exceptional, (1 review)
"The house was clean, spacious, well-appointed, convenient to the port, swimming, the grocery, the church, the village center, shops, and had gorgeous views. "
United States
Maria N.
The price is CA $121
CA $247 total
includes taxes & fees
Feb 10 - Feb 11
Casa dos Felicias

Casa Baleia Laranja Ocean-Front

Casa Baleia Laranja Ocean-Front
Madalena
10.0 out of 10, Exceptional, (3 reviews)
"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 CA $194
CA $330 total
includes taxes & fees
Feb 10 - Feb 11
Casa Baleia Laranja Ocean-Front

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 $355
CA $355 total
includes taxes & fees
Feb 10 - Feb 11
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Panoramic Ocean Views from your Private Varand

Panoramic Ocean Views from your Private Varand
São Roque do Pico
The price is CA $200
CA $253 total
includes taxes & fees
Feb 10 - Feb 11
Panoramic Ocean Views from your Private Varand

Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is CA $275
CA $373 total
includes taxes & fees
Feb 21 - Feb 22
Holiday Home 'Adega Pérola' with Wi-Fi

Silveira House

Silveira House
Lajes do Pico
The price is CA $73
CA $142 total
includes taxes & fees
Feb 11 - Feb 12
Silveira House

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 $248
CA $248 total
includes taxes & fees
Feb 10 - Feb 11
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

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
The price is CA $502
CA $571 total
includes taxes & fees
Feb 10 - Feb 11
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

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 $319
CA $319 total
includes taxes & fees
Feb 10 - Feb 11
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

Very well equipped apartment in the center of São Roque do Pico

Very well equipped apartment in the center of São Roque do Pico
São Roque do Pico
The price is CA $145
CA $275 total
includes taxes & fees
Feb 10 - Feb 11
Very well equipped apartment in the center of São Roque do Pico

Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace and Wi-Fi

Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace and Wi-Fi
Santo António SRP
The price is CA $443
CA $545 total
includes taxes & fees
Mar 1 - Mar 2
Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace and Wi-Fi

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 $591
CA $660 total
includes taxes & fees
Feb 10 - Feb 11
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

Lofts Azul Pastel

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

Porto Pim Bay

Porto Pim Bay
Horta
9.6 out of 10, Exceptional, (31 reviews)
"Exceptional place to stay. Clean, professional and caring staff; can’t wait to come back. "
United States
Joseph
The price is CA $210
CA $218 total
includes taxes & fees
Mar 1 - Mar 2
Porto Pim Bay

Horta Bay

Horta Bay
3.5 star property
Horta
10.0 out of 10, Exceptional, (6 reviews)
"The best place I ever been in faial island I love it ❤️❤️❤️❤️❤️👌"
United States
samuel
Horta Bay

Herdade das Hortênsias

Herdade das Hortênsias
São Jorge
10.0 out of 10, Exceptional, (1 review)
"Ruhig gelegen mit genügend Platz."
Germany
Lukas R.
The price is CA $129
CA $191 total
includes taxes & fees
Feb 28 - Mar 1
Herdade das Hortênsias

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, (1 review)
"serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso."
Portugal
Pedro E.
The price is CA $315
CA $357 total
includes taxes & fees
Feb 10 - Feb 11
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

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, (4 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 $336
CA $396 total
includes taxes & fees
Feb 10 - Feb 11
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
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 Pico Island Hotel Reviews

Find out more about Pico Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pico Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.