Pico Island Vacation Rentals

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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)
"Wonderful stay. Beautiful units with great hospitality"
United States
Adam
The price is CA $112
CA $117 total
includes taxes & fees
Apr 15 - Apr 16
Aldeia das Adegas

Aldeia dos Caldeirões

Aldeia dos Caldeirões
4.0 star property
Madalena
The price is CA $133
CA $138 total
includes taxes & fees
Apr 20 - Apr 21
Aldeia dos Caldeirões

Refúgio da Montanha

Refúgio da Montanha
3.0 star property
Sao Roque do Pico
10.0 out of 10, Exceptional, (3 reviews)
"The view, the surroundings, the pool!!! The house is very convenient and has everything you need! "
United States
hilde F. J.
The price is CA $149
CA $154 total
includes taxes & fees
Apr 14 - Apr 15
Refúgio da Montanha

Panoramic Ocean Views from your Private Varand

Panoramic Ocean Views from your Private Varand
São Roque do Pico
Panoramic Ocean Views from your Private Varand

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 $653
CA $722 total
includes taxes & fees
Apr 14 - Apr 15
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
Lajes do Pico
The price is CA $214
CA $214 total
includes taxes & fees
Apr 14 - Apr 15
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

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 $227
CA $368 total
includes taxes & fees
Apr 14 - Apr 15
Casa Baleia Laranja Ocean-Front

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 $303
CA $303 total
includes taxes & fees
Apr 14 - Apr 15
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines

Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines
São Roque do Pico
The price is CA $519
CA $683 total
includes taxes & fees
Apr 14 - Apr 15
Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines

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 $376
CA $376 total
includes taxes & fees
Apr 14 - Apr 15
Vacation Home "Adega Do Portinho Velho" with Balcony & 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 $285
CA $285 total
includes taxes & fees
Apr 14 - Apr 15
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is CA $151
CA $250 total
includes taxes & fees
Apr 15 - Apr 16
Holiday Home 'Adega Pérola' with Wi-Fi

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 $99
CA $99 total
includes taxes & fees
Apr 14 - Apr 15
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

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 $505
CA $607 total
includes taxes & fees
May 1 - May 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 $801
CA $871 total
includes taxes & fees
Apr 14 - Apr 15
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

Silveira House

Silveira House
Lajes do Pico
The price is CA $73
CA $143 total
includes taxes & fees
Apr 26 - Apr 27
Silveira House

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
The price is CA $116
CA $121 total
includes taxes & fees
Apr 16 - Apr 17
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 $151
CA $157 total
includes taxes & fees
Apr 14 - Apr 15
Porto Pim Bay

Casas do Pinheiro

Casas do Pinheiro
4.0 star property
Horta
7.6 out of 10, Good, (4 reviews)
"Very Nice quiet all new and clean "
United States
ELIEZER
The price is CA $140
CA $146 total
includes taxes & fees
Apr 15 - Apr 16
Casas do Pinheiro

Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
Topo Calheta São Jorge Açores
The price is CA $187
CA $187 total
includes taxes & fees
Apr 14 - Apr 15
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
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

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.