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São Jorge Island Vacation Rentals

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In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for São Jorge Island vacation rentals

Beach
Herdade das Hortênsias

Herdade das Hortênsias

Herdade das Hortênsias
São Jorge
10.0 out of 10, Exceptional, (1)
"Ruhig gelegen mit genügend Platz."
Germany
Lukas R.
$134 nightly
The price is $134
Dec 26 - Dec 27
Total with taxes and fees
Herdade das Hortênsias
Terrace/patio
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

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
$90 nightly
The price is $90
Jan 8 - Jan 9, 2026
Total with taxes and fees
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
Outdoor pool
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

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)
"serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso."
Portugal
Pedro E.
$251 nightly
The price is $251
Jan 2 - Jan 3, 2026
Total with taxes and fees
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
Outdoor pool
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)

Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
São Jorge
10.0 out of 10, Exceptional, (4)
"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.
$266 nightly
The price is $276
Jan 2 - Jan 3, 2026
Total with taxes and fees
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
Outdoor pool
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
São Jorge
$172 nightly
The price is $172
Jan 2 - Jan 3, 2026
Total with taxes and fees
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
Outdoor pool
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
Calheta
$188 nightly
The price is $195
Jan 2 - Jan 3, 2026
Total with taxes and fees
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
Outdoor pool
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)

Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
São Jorge
$253 nightly
The price is $253
Jan 2 - Jan 3, 2026
Total with taxes and fees
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
Outdoor pool
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba
São Jorge
$242 nightly
The price is $242
Jan 8 - Jan 9, 2026
Total with taxes and fees
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba
Exterior
Aldeia das Adegas

Aldeia das Adegas

Aldeia das Adegas
4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (63)
"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
$81 nightly
The price is $85
Jan 1 - Jan 2, 2026
Total with taxes and fees
Aldeia das Adegas
Exterior
Casa dos Felicias

Casa dos Felicias

Casa dos Felicias
São Roque do Pico
10.0 out of 10, Exceptional, (1)
"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.
$180 nightly
The price is $180
Dec 25 - Dec 26
Total with taxes and fees
Casa dos Felicias
Property grounds
Vila Paim - Apart. Low

Vila Paim - Apart. Low

Vila Paim - Apart. Low
São Roque do Pico
10.0 out of 10, Exceptional, (1)
"Great getaway super quiet and very relaxing place."
United States
Joe F.
$145 nightly
The price is $180
Dec 25 - Dec 26
Total with taxes and fees
Vila Paim - Apart. Low
Property grounds
Casa Baleia Laranja Ocean-Front

Casa Baleia Laranja Ocean-Front

Casa Baleia Laranja Ocean-Front
Madalena
10.0 out of 10, Exceptional, (3)
"The location of the property was wonderful. We could hear the waves crashing throughout our stay. Thank you again "
United States
Sebastien B.
$264 nightly
The price is $264
Dec 28 - Dec 29
Total with taxes and fees
Casa Baleia Laranja Ocean-Front
Private kitchen
Silveira House

Silveira House

Silveira House
Lajes do Pico
$104 nightly
The price is $104
Jan 18 - Jan 19, 2026
Total with taxes and fees
Silveira House
Fridge, microwave, oven, stovetop
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

Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
Lajes do Pico
$57 nightly
The price is $57
Dec 25 - Dec 26
Total with taxes and fees
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
1 bedroom
Very well equipped apartment in the center of São Roque do Pico

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
"I stayed in this apartment with my family of 4. The apartment itself was small but ok. Note that the management keeps the remote control for AC and if you need it, they charge a daily fee of 10EUR per day. The communication with the manager has been very difficult since the beginning. I’ve sent a message a month prior to arrival to confirm there was enough room for the 4 of us. I never got any answers. The day before our arrival, I sent another message that was again unanswered. Even VRBO...
Canada
Caroline P.
$215 nightly
The price is $215
Jan 20 - Jan 21, 2026
Total with taxes and fees
Very well equipped apartment in the center of São Roque do Pico
2 bedrooms, iron/ironing board, WiFi, bed sheets
Adega do Mirante

Adega do Mirante

Adega do Mirante
São Roque do Pico
8.0 out of 10, Very Good, (1)
"The basic necessities are provided; beds are comfortable and the place is clean. Need to Whatsapp owner to get information to get onto the property because messaging in Portugese otherwise. Property said air conditioning but the air conditioning was broken. It was cool enough though so not a problem. Walkable to the ocean and natural pool and nice restaurant down the street. It is located in Sao Roque which is in the middle of the island so nothing is far away if you are driving. Parking ample...
United States
Sharon
$180 nightly
The price is $180
Dec 25 - Dec 26
Total with taxes and fees
Adega do Mirante
TV
Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
$169 nightly
The price is $169
Dec 26 - Dec 27
Total with taxes and fees
Holiday Home 'Adega Pérola' with Wi-Fi
Property grounds
Amazing One Bedroom Apartment with Sea View

Amazing One Bedroom Apartment with Sea View

Amazing One Bedroom Apartment with Sea View
São Roque do Pico
$94 nightly
The price is $94
Dec 25 - Dec 26
Total with taxes and fees
Amazing One Bedroom Apartment with Sea View
Outdoor dining
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

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)
"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 traveler
$258 nightly
The price is $258
Dec 25 - Dec 26
Total with taxes and fees
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
TV
Vila Paim - Apart. DELUX

Vila Paim - Apart. DELUX

Vila Paim - Apart. DELUX
São Roque do Pico
$253 nightly
The price is $276
Dec 25 - Dec 26
Total with taxes and fees
Vila Paim - Apart. DELUX
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

Casa do Zé - AL

Casa do Zé - AL

10/10 Excellent
"The Casa do Ze is very well equipped with all utensils and essentials for cooking your own meals. The coffee maker is a moka pot, (first time using one) that makes great espresso. Bathroom supplies are also provided. The Casa is located at the end of a street and is a renovated old home, so it's more authentic than some other stays. The communication with the owner was excelent. WiFi was OK but sometimes cut out. Also, hot water supply was finicky as sometimes there would be plenty and other times none."
Lorne 5-night trip
Posted 2 months ago
Casa do Zé - AL

Find out more about São Jorge Island

Everything you need to know about São Jorge Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the São Jorge Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect São Jorge Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

São Jorge Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in São Jorge Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit São Jorge Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $85 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on São Jorge Island rentals

At Expedia, we put the best São Jorge Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top São Jorge Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream São Jorge Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around São Jorge Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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