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São João Holiday Rentals

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Our top choices for São João holiday rentals

1. Silveira House

Silveira House
Lajes do Pico
The price is NZ$172
includes taxes & fees
6 Sept - 7 Sept
Silveira House

2. Aldeia das Adegas

Aldeia das Adegas
4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (68 reviews)
"We had a great stay here."
United States
Nicholas
The price is NZ$211
includes taxes & fees
22 Sept - 23 Sept
Aldeia das Adegas

3. Aldeia dos Caldeirões

Aldeia dos Caldeirões
4.0 star property
Madalena
8.8 out of 10, Excellent, (3 reviews)
"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...
Canada
Evan
The price is NZ$200
includes taxes & fees
2 Sept - 3 Sept
Aldeia dos Caldeirões

4. 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
6.0 out of 10, (1 review)
"Pros: Die Ruhe, der Ausblick, der private Parkplatz, die schnelle Unterstützung durch die Ansprechperson, der Insektenschutz an Fenstern Cons: Schwierigkeit gehabt das Haus zu finden, da das einzige Schild am Haus selbst hängt und von der Straße aber nicht zu erkennen war; leichter Schimmel in der Dusche; penetranter Duft der Duftspender in Küche und Bad; Bettwäsche roch nicht sehr frisch"
Germany
Anonymous traveller
The price is NZ$476
includes taxes & fees
29 Aug - 30 Aug
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

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

Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
Ribeiras
The price is NZ$472
includes taxes & fees
21 Sept - 22 Sept
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

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

Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
Prainha
The price is NZ$669
includes taxes & fees
4 Sept - 5 Sept
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning

7. 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
7.0 out of 10, Good, (2 reviews)
"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 NZ$1,102
includes taxes & fees
1 Sept - 2 Sept
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

8. 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 NZ$786
includes taxes & fees
9 Sept - 10 Sept
Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace & Wi-Fi

9. 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 NZ$1,272
includes taxes & fees
1 Sept - 2 Sept
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

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

Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
Lajes do Pico
The price is NZ$155
includes taxes & fees
4 Sept - 5 Sept
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

11. 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 NZ$512
includes taxes & fees
27 Aug - 28 Aug
SKY MOUNTAIN & SEA SMS-AZORES

12. Lofts Azul Pastel

Lofts Azul Pastel
4.0 star property
Horta
9.6 out of 10, Exceptional, (40 reviews)
"Room was spacious and had a lovely ocean view. Property was clean and fresh. Convenient location. Would recommend! Staff was helpful and responsive through email with the check in process as I had arrived early before the room was ready."
United States
Miriam
The price is NZ$245
includes taxes & fees
27 Aug - 28 Aug
Lofts Azul Pastel

13. Casa do Jardim

Casa do Jardim
Santo Amaro
The price is NZ$412
includes taxes & fees
18 Sept - 19 Sept
Casa do Jardim

14. 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 NZ$548
includes taxes & fees
6 Sept - 7 Sept
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

15. Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines

Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines
São Roque do Pico
The price is NZ$1,151
includes taxes & fees
25 Aug - 26 Aug
Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines

16. 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 NZ$875
includes taxes & fees
1 Sept - 2 Sept
Casa Baleia Laranja Ocean-Front

17. 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 NZ$386
includes taxes & fees
5 Sept - 6 Sept
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

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

Apartment 'Valverdeapart' with Private Terrace and Wi-Fi
Madalena
The price is NZ$357
includes taxes & fees
6 Sept - 7 Sept
Apartment 'Valverdeapart' with Private Terrace and Wi-Fi

19. Bearsu Nature Almoxarife

Bearsu Nature Almoxarife
2.0 star property
Horta
8.6 out of 10, Excellent, (7 reviews)
"Nice camping near the sea"
Italy
Leonardo
The price is NZ$86
includes taxes & fees
17 Sept - 18 Sept
Bearsu Nature Almoxarife

20. Casa da Petra – Our Casa is your Casa

Casa da Petra – Our Casa is your Casa
Urzelina
The price is NZ$770
includes taxes & fees
21 Sept - 22 Sept
Casa da Petra – Our Casa is your Casa
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 João Hotel Reviews

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?

Pico Azores - Family house S. Jorge view: This holiday home rental outside of São João offers a balcony, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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. Convent of Sao Roque do Pico 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.