São João Holiday Rentals from NZ$117: Search Short-Term Rentals

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

Villa Lucinda ..... : This highly rated holiday home rental in São João is located on the beach, and offers a balcony, laundry facilities and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, an oven and a microwave.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for São João holiday rentals

A stone building with a red roof, a paved pathway, and a stone wall with a red railing.

1. Aldeia das Adegas

Sao Roque do Pico

Nicholas

includes taxes & fees

1 Nov - 2 Nov

A wooden table and bench in a garden with a hot tub and a glass door leading to a room.

2. Aldeia dos Caldeirões

Madalena

"The place is beautiful, in a great location, private and secluded, with nice amenities such as hot tubs, pool, wood BBQ. It looks just like the pictures and overall, we enjoyed our stay. But, - very limited hot water. Takes long to warm up and then only lasts 5 minutes. Not enough for 2 showers. We could only fill the amazing bath up a few inches before it got cold, so kind of useless. - lots of ants, and when we complained, we were told to deal with it ourselves - there was a birds nest...

Evan

includes taxes & fees

1 Nov - 2 Nov

A white building with grey trim, a stone wall, and a small garden with various plants.

3. Silveira House

Lajes do Pico

A modern interior with a large sliding glass door leading to a balcony, wooden beams on the ceiling, and a dark wall.

4. Porto Pim Bay

Horta

Joseph

includes taxes & fees

3 Nov - 4 Nov

A stone-walled room with a white chair and table, a window, and a view of a landscape.

5. Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Lajes do Pico

Anonymous traveller

includes taxes & fees

31 Oct - 1 Nov

A rectangular pool with clear blue water, surrounded by a tiled deck.

6. Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

Ribeiras

includes taxes & fees

10 Oct - 11 Oct

A poolside dining area with a view of the ocean, featuring burgers and fries on the table.

7. Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

Lajes do Pico

includes taxes & fees

7 Nov - 8 Nov

A modern room with wooden beams, a white sofa, a round table, and a view of the sea through a window.

8. Lofts Azul Pastel

Horta

Cathy

includes taxes & fees

8 Nov - 9 Nov

View all properties

Find holiday rentals that suit your style

Apartments

Private holiday homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top São João Hotel Reviews

Hotel Caravelas

10/10 Excellent

"Location next to ferry is perfect, rooms clean great breakfast. 100%"

The Book Hotel

10/10 Excellent

"Every single staff member was warm and welcoming. The hotel is well-maintained and the room was very clean. The Japanese toilet in the room was a nice amenity, and toiletries were also available on the bathroom counter. The bed was comfortable and I like the different lighting options you can use. The pool was my favorite feature of the hotel. It's on the roof where you can also access the spa. The pool and hot tub are connected so you can easily switch from one to the other. It's a small, shallow pool, so there is no diving and not much room to swim - all you can pretty much do is just float in the pool, which is really all you need. The hotel is a block away from a park/garden and a couple of blocks away from the marina. Everything is walkable. The front desk staff were very helpful. They gave me great suggestions for restaurants, shopping, and even helped me reserve a taxi tour of the island. I will definitely be staying here again."

Azores Youth Hostels - Pico

10/10 Excellent

"The hostel is such a lovely place, very good located and the staff was really helpful, wherever you need they are always there to help you. Very nice and peaceful place. 100% recommended. The unic thing that I missed was a kitchen so you can cook your own food. But there are very nice local restaurants beside the hostel."

Find out more about São João

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our São João holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up São João. 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 São João. Seeing all the best attractions is bound to make you fall in love with São João. Who knows, you may even be tempted to extend your 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 holiday 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 São João short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in São João?

Yes, there are holiday rentals close to the most popular sights in São João, or you can select a more secluded option if you're looking for a relaxing stay.

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

Villa Lucinda .....: This highly rated holiday home rental in São João is located on the beach, and offers a balcony, laundry facilities and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, an oven and a microwave.

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. Azores Wine Company and Pico Island Vineyard Culture are a couple of places you'll find in the wider area.

What’s a holiday rental in São João like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in São João. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for family trips.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for São João holiday rentals

1. Aldeia das Adegas

2. Aldeia dos Caldeirões

3. Silveira House

4. Porto Pim Bay

5. Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

6. Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

7. Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

8. Lofts Azul Pastel

9. Vista da Baía - Casa do Aniceto Apartment with Sea View, Private Terrace & Wi-Fi

10. Casa do Laureano

11. Casa da Terra Alta

12. Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning

13. Apartment 'Valverdeapart' with Private Terrace and Wi-Fi

14. Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

15. Holiday Home 'Adega Pérola' with Wi-Fi

16. Pico Azores - Family house S. Jorge view

17. Casa Baleia Laranja Ocean-Front

18. Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

19. Horta Bay

20. Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

Find holiday rentals that suit your style

Top São João Hotel Reviews

Hotel Caravelas

Vinhas do Calhau

Aldeia da Fonte Hotel

Internacional Azores Boutique

Hotel do Canal

The Book Hotel

Casa do Zé - AL

Azoris Faial Garden

Azores Youth Hostels - Pico

Find out more about São João

Frequently asked questions

Go further with the Expedia app