A coastal town with a prominent hill and a rainbow over the sea.

São Jorge Island Vacation Rentals

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Our top choices for São Jorge Island vacation rentals

Carpe Diem Apartment

Carpe Diem Apartment
Urzelina
The price is CA $273
CA $283 total
includes taxes & fees
Aug 3 - Aug 4
Carpe Diem Apartment

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 $259
CA $259 total
includes taxes & fees
Aug 10 - Aug 11
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

Casa da Petra – Our Casa is your Casa

Casa da Petra – Our Casa is your Casa
Urzelina
The price is CA $763
CA $763 total
includes taxes & fees
Aug 2 - Aug 3
Casa da Petra – Our Casa is your Casa

Carpe Noctem Apartment

Carpe Noctem Apartment
Urzelina
The price is CA $273
CA $283 total
includes taxes & fees
Aug 10 - Aug 11
Carpe Noctem Apartment

Aldeia das Adegas

Aldeia das Adegas
4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (66 reviews)
"We had a great stay here."
United States
Nicholas
The price is CA $355
CA $369 total
includes taxes & fees
Aug 16 - Aug 17
Aldeia das Adegas

Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is CA $411
CA $509 total
includes taxes & fees
Aug 19 - Aug 20
Holiday Home 'Adega Pérola' with Wi-Fi

Casa do Laureano

Casa do Laureano
Santo Amaro
Casa do Laureano

Casa do Jardim

Casa do Jardim
Santo Amaro
Casa do Jardim

Casa da Terra Alta

Casa da Terra Alta
Santo Amaro
The price is CA $417
CA $469 total
includes taxes & fees
Jul 31 - Aug 1
Casa da Terra Alta

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 $529
CA $529 total
includes taxes & fees
Aug 24 - Aug 25
Vacation Home "Adega Do Portinho Velho" with Balcony & 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 $392
CA $392 total
includes taxes & fees
Aug 22 - Aug 23
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Silveira House

Silveira House
Lajes do Pico
The price is CA $72
CA $141 total
includes taxes & fees
Aug 2 - Aug 3
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 $317
CA $317 total
includes taxes & fees
Aug 4 - Aug 5
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

SKY MOUNTAIN & SEA SMS-AZORES

SKY MOUNTAIN & SEA SMS-AZORES
São Roque do Pico
2.0 out of 10, (1 review)
"Airline canceled our flight. I emailed the host i had no response. "
United States
Thomas M.
The price is CA $401
CA $533 total
includes taxes & fees
Aug 6 - Aug 7
SKY MOUNTAIN & SEA SMS-AZORES

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

Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace & Wi-Fi
Santo António SRP
The price is CA $558
CA $646 total
includes taxes & fees
Aug 20 - Aug 21
Apartment 'Vista Da Baía - Casa Do Aniceto' 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 $631
CA $631 total
includes taxes & fees
Aug 19 - Aug 20
Apartment 'Branca' 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 $1,087
CA $1,155 total
includes taxes & fees
Aug 28 - Aug 29
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & 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 $610
CA $808 total
includes taxes & fees
Aug 16 - Aug 17
Casa Baleia Laranja Ocean-Front

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
6.0 out of 10, (1 review)
"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 $1,028
CA $1,097 total
includes taxes & fees
Aug 24 - Aug 25
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & 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 São Jorge Island Hotel Reviews

Find out more about São Jorge 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 São Jorge 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.