São Jorge 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 São Jorge Island vacation rentals

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 $328
CA $387 total
includes taxes & fees
Mar 13 - Mar 14
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
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 $307
CA $348 total
includes taxes & fees
Mar 13 - Mar 14
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
The price is CA $307
CA $348 total
includes taxes & fees
Mar 16 - Mar 17
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
The price is CA $224
CA $263 total
includes taxes & fees
Mar 12 - Mar 13
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
The price is CA $145
CA $145 total
includes taxes & fees
Mar 13 - Mar 14
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
The price is CA $202
CA $230 total
includes taxes & fees
Mar 12 - Mar 13
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

Vacation Home in São Jorge

Herdade das Hortênsias
10.0 out of 10, Exceptional, (1 review)
"Ruhig gelegen mit genügend Platz."
Germany
Lukas R.
The price is CA $120
CA $180 total
includes taxes & fees
Mar 14 - Mar 15
Herdade das Hortênsias
The price is CA $292
CA $331 total
includes taxes & fees
Mar 12 - Mar 13
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

Apartment in Sao Roque do Pico

Aldeia das Adegas
4.0 star property
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 $109
CA $114 total
includes taxes & fees
Mar 12 - Mar 13
Aldeia das Adegas
The price is CA $490
CA $558 total
includes taxes & fees
Mar 12 - Mar 13
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
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 $346
CA $346 total
includes taxes & fees
Mar 13 - Mar 14
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
The price is CA $577
CA $644 total
includes taxes & fees
Mar 12 - Mar 13
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi
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 $189
CA $322 total
includes taxes & fees
Mar 13 - Mar 14
Casa Baleia Laranja Ocean-Front
The price is CA $242
CA $242 total
includes taxes & fees
Mar 12 - Mar 13
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
The price is CA $288
CA $387 total
includes taxes & fees
Mar 12 - Mar 13
Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace and Wi-Fi
The price is CA $242
CA $242 total
includes taxes & fees
Mar 12 - Mar 13
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

Vacation Home in Cais do Galego

Holiday Home 'Adega Pérola' with Wi-Fi
The price is CA $130
CA $226 total
includes taxes & fees
Mar 16 - Mar 17
Holiday Home 'Adega Pérola' with Wi-Fi

Vacation Home in Lajes do Pico

Silveira House
The price is CA $71
CA $139 total
includes taxes & fees
Mar 12 - Mar 13
Silveira House
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

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.