São João Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in São João

Aerial view
Lofts Azul Pastel

Lofts Azul Pastel

4.0 star property
Horta
9.8 out of 10, Exceptional, (33)
"Beautiful stay and wonderful staff!"
United States
Cathy
Lofts Azul Pastel
Exterior
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
The price is ￥17,397
￥18,094 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Aldeia das Adegas
Daily buffet breakfast (EUR 10 per person)
Horta Bay

Horta Bay

3.5 star property
Horta
10.0 out of 10, Exceptional, (5)
"Amazing from start to finish! Joe (owner) is so kind and welcoming. Great property, great location! Can't wait to come back!"
United States
Admin
Horta Bay
Exterior
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.
The price is ￥13,570
￥27,683 total
includes taxes & fees
Dec 11 - Dec 12
Casa dos Felicias
Property grounds
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.
The price is ￥8,142
￥27,683 total
includes taxes & fees
Dec 11 - Dec 12
Vila Paim - Apart. Low
2 bedrooms, iron/ironing board, WiFi, bed sheets
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
The price is ￥13,585
￥27,713 total
includes taxes & fees
Dec 20 - Dec 21
Adega do Mirante
Private kitchen
Silveira House

Silveira House

Lajes do Pico
The price is ￥8,142
￥15,922 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Silveira House
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

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.
The price is ￥16,284
￥33,111 total
includes taxes & fees
Dec 30 - Dec 31
Very well equipped apartment in the center of São Roque do Pico
Property grounds
Amazing One Bedroom Apartment with Sea View

Amazing One Bedroom Apartment with Sea View

São Roque do Pico
The price is ￥14,475
￥14,475 total
includes taxes & fees
Dec 11 - Dec 12
Amazing One Bedroom Apartment with Sea View
Outdoor pool
Aldeia dos Caldeirões

Aldeia dos Caldeirões

3.0 star property
Madalena
The price is ￥15,658
￥16,284 total
includes taxes & fees
Dec 5 - Dec 6
Aldeia dos Caldeirões
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

Lajes do Pico
The price is ￥8,837
￥8,837 total
includes taxes & fees
Dec 11 - Dec 12
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Apartment 'Casa Da Travessa Com 3 Quartos' with Wi-Fi

Apartment 'Casa Da Travessa Com 3 Quartos' with Wi-Fi

Horta
10.0 out of 10, Exceptional, (1)
"This was a wonderful property in the Old Town of Funchal. Many shops and restaurants right outside our door. Centrally located by the taxi and buses as well as the cable car. "
United States
Dean Q.
The price is ￥30,893
￥30,893 total
includes taxes & fees
Dec 5 - Dec 6
Apartment 'Casa Da Travessa Com 3 Quartos' with Wi-Fi
1 bedroom, WiFi, bed sheets
Aligus 1 | Uma horta na Horta

Aligus 1 | Uma horta na Horta

Horta
The price is ￥9,047
￥15,923 total
includes taxes & fees
Dec 18 - Dec 19
Aligus 1 | Uma horta na Horta
Fridge, microwave, oven, stovetop
Apartment 'Casa Da Travessa Piso Térreo' with Private Terrace, Balcony and Wi-Fi

Apartment 'Casa Da Travessa Piso Térreo' with Private Terrace, Balcony and Wi-Fi

Horta
9.0 out of 10, Wonderful, (2)
"This was a great place to spend our 3 days on the island. It had everything we needed or wanted and the hosts even left us a little gift. Highly recommend!"
Canada
Crystal V.
The price is ￥26,480
￥26,480 total
includes taxes & fees
Dec 18 - Dec 19
Apartment 'Casa Da Travessa Piso Térreo' with Private Terrace, Balcony and Wi-Fi
TV
Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi

Cais do Galego
The price is ￥15,905
￥26,950 total
includes taxes & fees
Dec 9 - Dec 10
Holiday Home 'Adega Pérola' with Wi-Fi
Interior
Apartment 'Azores4fun' with Wi-Fi

Apartment 'Azores4fun' with Wi-Fi

Horta
8.8 out of 10, Excellent, (3)
"The accommodation is amazing. It is clean, spacious, has all needed appliance. It is located near the port with easy access to cafes, shops and restaurants. The owner helped us a lot as we had problems with flights. We really enjoyed to spend our time in this place."
Germany
Vasily P.
The price is ￥22,067
￥22,067 total
includes taxes & fees
Dec 10 - Dec 11
Apartment 'Azores4fun' with Wi-Fi
Outdoor dining
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
The price is ￥39,761
￥39,761 total
includes taxes & fees
Dec 5 - Dec 6
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
Outdoor dining
Apartment 'Ladomar Avenida' with Private Terrace, Private Garden and Wi-Fi

Apartment 'Ladomar Avenida' with Private Terrace, Private Garden and Wi-Fi

Horta
10.0 out of 10, Exceptional, (1)
"Pros: We were upgraded to a three bedroom apartment in the same block. The apartment is very spacious with an attractive terrace and fabulous view of Pico island. It is very tastefully furnished with antiques which have been lovingly restored. Dora was very kind and communication with her was excellent. She left us a lovely welcome hamper of local food. Highly recommended property. Cons: Only the weather!"
United States
Anonymous traveler
The price is ￥33,134
￥33,134 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Apartment 'Ladomar Avenida' with Private Terrace, Private Garden and Wi-Fi
Property grounds
Beautiful One Bedroom Apartment near the sea in Sao Roque do Pico

Beautiful One Bedroom Apartment near the sea in Sao Roque do Pico

São Roque do Pico
The price is ￥14,475
￥14,475 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Beautiful One Bedroom Apartment near the sea in Sao Roque do Pico
Microwave, oven, stovetop, dishwasher
Panoramic Ocean Views from your Private Varand

Panoramic Ocean Views from your Private Varand

São Roque do Pico
The price is ￥22,346
￥28,306 total
includes taxes & fees
Dec 7 - Dec 8
Panoramic Ocean Views from your Private Varand
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.
View all properties
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

Pico TERRAMAR & SPA

Pico TERRAMAR & SPA

10/10 Excellent
"Staff were great. I arrived early from my flight & they quickly got my room ready so I could unoack & relax. Meal was excellent."
Deirdre Janine 1-night trip
Posted 11 days ago
Pico TERRAMAR & SPA

Find out more about São João

Search for holiday rentals in São João on Expedia! You can easily find your home rentals, villas, holiday apartments in São João using one of the methods below:

  • View our selection of featured holiday rentals in São João
  • Use the map to find apartments and other holiday homes in the São João neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in São João while they last

Look no further and take a look at our great range of rental properties in São João!

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?

Panoramic Ocean Views from your Private Varand: This vacation home rental near São João is equipped with a barbecue grill, laundry facilities, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop, 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. Pico Island Vineyard Culture and Porto Pim Whale Factory Museum 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.