São João Vacation Rentals from ￥10,355: Search Short-Term Rentals

Q: What are some of the best vacation rentals that São João has to offer?

Cantinho do Avô - Pico Island - Prainha, São Roque do Pico : This vacation home near São João offers a patio, a garden, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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Vacation Rentals in São João

Situated on a cliff overlooking the sea, this house offers a scenic view of the surrounding greenery and water.

"Our hosts were amazing! They left us a welcome basket that served us very well for our late arrival and for the entire week. We’ve had three rentals and they were the only ones that did that. The view and location, near a natural swimming hole, worked very well for us."

Overlooking a rugged coastline, this property offers breathtaking views of a volcanic mountain and the ocean.

"Very nice experience, the area was kept clean and everything was in good conditopn."

￥10,769 total

includes taxes & fees

Aug 25 - Aug 26

Overlooking a picturesque coastal town with a majestic mountain backdrop, this scenic view features a mix of homes and businesses, a prominent white building, and a rugged coastline with clear waters.

"Beautiful stay and wonderful staff!"

Experience the charm of a traditional European village, surrounded by historic stone buildings and a tranquil atmosphere.

"Wonderful stay. Beautiful units with great hospitality"

￥27,482 total

includes taxes & fees

Jul 29 - Jul 30

Relax on the patio overlooking the pool and lush landscape with a stone table and wicker chairs.

"Lovely cabin with a killer sea view. Warm, efficient welcome from the staff. Great accommodation, clean, brand new. Highest recommendation. "

Relax by the serene pool surrounded by a tranquil view of calm water and distant hills.

"Asan was a great host. Quiet place, very roomy and clean, the view is amazing. Every thing was in place to enjoy a confortable stay. "

Enjoy breathtaking views of the ocean and surrounding mountains from this balcony, featuring a picturesque lighthouse in the distance.

"Stay was amazing. The location was great, cafe right next door and easy walk to pier and restaurants. Owner is super sweet, helped us get a ride to airport and was cheaper than a taxi. Also has laundry services which helped tremendously. Would stay there again no question!"

Escape to a serene oasis surrounded by lush greenery and majestic mountains.

"L'appartamento ha un potenziale enorme, se solo fosse gestita come si dovrebbe Ho prenotato ad aprile per 4 giorni ad agosto...ho contattato l'host 3 giorni prima di arrivare ma non mi ha risposto...il giorno dopo l'ho contattata con wattsapp e dopo vari messaggi e telefonate sono riuscita ad avere risposta per l'orario del check-in La casa e' nolto bella e il posto e' favoloso, immerso nei vigneti"

Relax on the balcony with a wicker sofa and enjoy the serene views of the lush landscape and pool.

"We had such a relaxing stay at this beautiful home. My two kids loved the pool and the location next to the natural pools was amazing. Highly recommend!"

Overlooking the clear blue waters, this beachfront property offers a serene setting with lush greenery and a simple, functional architecture.

"Nice flat and Friendly staff. "

￥20,999 total

includes taxes & fees

Aug 1 - Aug 2

Enjoy a romantic dinner for two on this scenic balcony overlooking the sea.

"Very unique property. Great view. Loved the layout of property. For additional cost provided breakfast basket each day. Town has a well stocked grocery store nearby. Very picturesque village with a wonderful wine bar."

Cozy retreat with exposed beams, wooden panels, and a natural ambiance.

"We had a very peaceful and enjoyable stay, using the house as a base to climb Mt Pico, enjoy a whale watch and a wine tour. The host was very helpful with advice and helped arrange the wine tour and driver. The view out the back is beyond gorgeous and it’s a perfect deck to eat all your meals."

Surrounded by lush greenery, this resort offers a serene pathway leading to a majestic mountain view.

Guests can enjoy a refreshing swim in the pool surrounded by lush greenery and a prominent tree.

Enjoy breathtaking views of the distant mountain and sea from this room's expansive window and balcony.

"Adorable local cottage in a very small town. We stayed in the 2 bedroom apartment on the second floor. Neighbors gave us a walking tour and showed us their garden and taught us history of the area. "

Explore the rugged terrain and discover a hidden cave entrance along a winding dirt path.

"It was a wonderful place and our host was a beautiful caring lady."

Enjoy a romantic meal on the deck with a breathtaking view of the coastal landscape.

"Magnifique localisation; maison parfaitement équipée et commerces à moins de 100m."

Enjoy a meal or relax in this sheltered outdoor seating area with a view of the sea and surrounding landscape.

Relax in this inviting living area with a stunning sea view, featuring a sofa, wicker chair, and decorative wall art.

"Friendly, very well situated, very calm and safe neighbourhood."

Experience the unique loft-style room with a sloped ceiling and rustic stone walls.

"The house is well equipped and the location excellent, although one must plan to walk 200 meters to reach the house which is on a peculiar road to deive. the host is suoer helpful and polite, the kitchen fully stocked."

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Top São João Hotel Reviews

Pico Dreams - Sportfish

10/10 Excellent

"We had a truly lovely stay at this charming guesthouse. The owner and her husband are without a doubt the sweetest people we met during our trip. On the morning of our departure, her husband even offered, completely on his own initiative, to drive us to the ferry. That level of kindness and hospitality is rare these days and deserves to be recognized. The place itself is spotless, cozy, and thoughtfully arranged. There’s a warm, welcoming atmosphere throughout, with a beautiful common area where you can relax and unwind after a day of exploring. You can tell that a lot of care goes into maintaining the property, it feels like a home, not just a rental. One of the highlights is the stunning view of Pico from the house. Waking up to that view each morning was a gift. Whether you’re enjoying your coffee outside or just soaking in the peace and quiet, the setting is perfect. Everything was well-organized, from check-in to check-out. The room was comfortable, the linens were fresh, and all the small details were in place. It’s clear that the owners take great pride in what they do and it shows. We would return in a heartbeat. Highly recommended if you’re looking for a genuine, heartwarming stay in the Azores. "

Pico Vineyards

8/10 Good

"This is a beautiful property that opened 10 days before we stayed, so they were still working out little issues. The staff was very solicitous and the wine tasting in the cave was a really nice experience. The pool for the main rooms is indoor and lovely. The VIP rooms have their own small pools. The breakfast on the terrace was lovely. There is no outdoor pool, bar or restaurant. "

Sara Village

8/10 Good

"We were warmly welcomed by Miguel, the owner/manager of the place. We experienced a slight inconvenience with our room at arrival, but Miguel quickly offered us a solution, which was suitable and much appreciated. The view from the terrace was incredible! This is related to the town and not to the lodging, but for dining options, at the time of the year that we went (early June) there were not much choices. But overall, a good experience! :)"

Find out more about São João

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Frequently asked questions

Are there vacation rentals in São João?

Yes, you can find vacation rentals close to the most popular local attractions in São João, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that São João has to offer?

Cantinho do Avô - Pico Island - Prainha, São Roque do Pico: This vacation home near São João offers a patio, a garden, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in São João?

Choose from 4 Expedia vacation rentals in São João for a memorable vacation.

What’s there to see and do in São João?

While you're exploring the area, São João Forest Reserve and Mount Pico are a couple of picturesque spots to get outside and enjoy nature. Pico Island Vineyard Culture and Porto Pim Beach are a couple of places you'll find in the larger area.

What’s a vacation rental in São João like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in São João. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.

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São João Vacation Rentals

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Vacation Rentals in São João

Aguada House - Welcome

Bearsu Nature Almoxarife

Lofts Azul Pastel

Aldeia das Adegas

Pico Terrace

A Casa do Ouvidor

Horta Bay

Cantinho do Avô - Pico Island - Prainha, São Roque do Pico

Cliff-Top Ocean-Fronted Villa With Gardens And Private Pool

Porto Pim Bay

Adegas do Pico

Pike Cliffs - Amazing view to S. Jorge

Refúgio da Montanha

Casa das Pereiras - Rural Tourism T2

Casa do Zé - AL

Faidoca's Grandfather House - Four-Bedroom House

House @ Porto Pim Beach - Supreme location on the most beautiful beach Azores

Férias de Sonho na Ilha do Pico, nos Açores

4 bedrooms & great view

A small cottage in the center of Horta, Faial Island, Azores

Top São João Hotel Reviews

Pico Dreams - Sportfish

Azoris Faial Garden

São Jorge Garden

Pico Vineyards

Vinhas do Calhau

Hotel Horta

Pousada Forte da Horta - Historic Hotel

Hotel do Canal

Sara Village

Find out more about São João

Frequently asked questions