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 $167
CA $174 total
includes taxes & fees
May 13 - May 14
Aldeia das Adegas

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 $221
CA $230 total
includes taxes & fees
May 13 - May 14
Refúgio da Montanha

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 $433
CA $433 total
includes taxes & fees
May 11 - May 12
Vacation Home "Adega Do Portinho Velho" with Balcony & 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 $708
CA $777 total
includes taxes & fees
May 11 - May 12
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

Aldeia dos Caldeirões

Aldeia dos Caldeirões
4.0 star property
Madalena
10.0 out of 10, Exceptional, (1 review)
"Superbe petite maison accueillante "
Canada
Eric
The price is CA $163
CA $170 total
includes taxes & fees
May 31 - Jun 1
Aldeia dos Caldeirões

Apartment 'Valverdeapart' with Private Terrace and Wi-Fi

Apartment 'Valverdeapart' with Private Terrace and Wi-Fi
Madalena
The price is CA $159
CA $258 total
includes taxes & fees
May 11 - May 12
Apartment 'Valverdeapart' with 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 $619
CA $800 total
includes taxes & fees
May 11 - May 12
Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines

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 $564
CA $753 total
includes taxes & fees
Jun 5 - Jun 6
Casa Baleia Laranja Ocean-Front

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 $914
CA $983 total
includes taxes & fees
May 11 - May 12
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

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 $301
CA $301 total
includes taxes & fees
May 11 - May 12
Holiday Home 'Adega Maciel' 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 $127
CA $226 total
includes taxes & fees
May 14 - May 15
Holiday Home 'Adega Pérola' with 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 $283
CA $283 total
includes taxes & fees
May 12 - May 13
Apartment 'Branca' with Sea View, Private Terrace and 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 $212
CA $212 total
includes taxes & fees
May 13 - May 14
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden 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 $217
CA $319 total
includes taxes & fees
May 31 - Jun 1
Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace and Wi-Fi

Silveira House

Silveira House
Lajes do Pico
The price is CA $73
CA $142 total
includes taxes & fees
May 18 - May 19
Silveira House

Bearsu Nature Almoxarife

Bearsu Nature Almoxarife
2.0 star property
Horta
8.8 out of 10, Excellent, (6 reviews)
"Nice camping near the sea"
Italy
Leonardo
The price is CA $64
CA $67 total
includes taxes & fees
May 22 - May 23
Bearsu Nature Almoxarife

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 $140
CA $145 total
includes taxes & fees
May 11 - May 12
Lofts Azul Pastel

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
The price is CA $387
CA $440 total
includes taxes & fees
May 11 - May 12
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

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 $403
CA $476 total
includes taxes & fees
May 11 - May 12
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

Apartment 'Ladomar Matriz' with Sea View, Private Terrace and Wi-Fi

Apartment 'Ladomar Matriz' with Sea View, Private Terrace and Wi-Fi
Horta
10.0 out of 10, Exceptional, (4 reviews)
"Pros: The host, the place, cleaning and comfort Cons: A little bit noisy."
United States
Anonymous traveller
The price is CA $708
CA $708 total
includes taxes & fees
May 11 - May 12
Apartment 'Ladomar Matriz' with Sea View, Private Terrace 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.