Prainha Holiday Rentals

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Check prices for these dates

Tonight
19 Dec - 20 Dec
Tomorrow
20 Dec - 21 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Prainha holiday rentals

Terrace/patio
Adegas do Pico

Adegas do Pico

Adegas do Pico
4.0 star property
Sao Roque do Pico
9.0 out of 10, Wonderful, (38)
"Very nice rural property "
United States
Mario
Adegas do Pico
Interior
Pike Cliffs - Amazing view to S. Jorge

Pike Cliffs - Amazing view to S. Jorge

Pike Cliffs - Amazing view to S. Jorge
Prainha de Cima
9.6 out of 10, Exceptional, (8)
"We stayed at Pike Cliffs in July. The house is lovely and suitable for 4-6 people. We really like the views, and were able to reach Francisco when we got lost getting to the place. Thank you Francisco!"
Canada
A C.
Pike Cliffs - Amazing view to S. Jorge
Front of property
Houses In Pico

Houses In Pico

Houses In Pico
3.0 star property
Sao Roque do Pico
8.6 out of 10, Excellent, (13)
"Pleasant surprise with gift basket and heater on at arrival! We never saw the host, but very accommodating online. Well equipped and nice location. On the downside, the beds and pillows are very hard."
Norway
Vibeke
Houses In Pico
Living room
Casas da Junqueira

Casas da Junqueira

Casas da Junqueira
4.0 star property
Sao Roque do Pico
9.2 out of 10, Wonderful, (12)
"A clean modern apartment. Bed was comfortable with nice sheets and pillows. Kitchen had basic cooking utensils but unfortunately not have basic items for cooking like salt, pepper, sugar, oil. Nice welcome basket of goodies was much appreciated."
Canada
Lorne
Casas da Junqueira
Exterior
Casa da Atafona - Quinta da Ribeira da Urze

Casa da Atafona - Quinta da Ribeira da Urze

Casa da Atafona - Quinta da Ribeira da Urze
Ribeira de Urze
10.0 out of 10, Exceptional, (1)
"Wir konnten hier eine sehr entspannte Ferienwoche genießen. Das Haus ist geräumig, luftig, sehr sauber. Die Vermieterin Salomé ist super nett und hilfreich."
Germany
Ina M.
Casa da Atafona - Quinta da Ribeira da Urze
4 bedrooms, desk, Internet
Liiiving in A Ores - Ocean View House

Liiiving in A Ores - Ocean View House

Liiiving in A Ores - Ocean View House
2.0 star property
Sao Roque do Pico
Liiiving in A Ores - Ocean View House
Property grounds
Casa da Avó - Quinta da Ribeira da Urze

Casa da Avó - Quinta da Ribeira da Urze

Casa da Avó - Quinta da Ribeira da Urze
Prainha de cima
8.4 out of 10, Very good, (5)
"Nice large rental property in rural Prainha de Cima. Host was very nice and accommodating. Clean apartment with everything you need for comfortable stay. Day trips are easy to Horta or Velas on the ferries. Recommended. Great value."
United States
Larry A.
Casa da Avó - Quinta da Ribeira da Urze
Exterior
Casa da Ribeira - Quinta da Ribeira da Urze

Casa da Ribeira - Quinta da Ribeira da Urze

Casa da Ribeira - Quinta da Ribeira da Urze
Ribeira de Urze
10.0 out of 10, Exceptional, (1)
"The house is spacious, and very quiet, we slept well! "
France
Audrey L.
Casa da Ribeira - Quinta da Ribeira da Urze
Outdoor dining
Great Tranquility Holiday Home

Great Tranquility Holiday Home

Great Tranquility Holiday Home
S.Roque do Pico
10.0 out of 10, Exceptional, (1)
"This place is a treasure. I highly recommend staying here. The hosts are amazing people and treat you like family. "
United States
Alex L.
Great Tranquility Holiday Home
View from property
Casa do Zé - AL

Casa do Zé - AL

Casa do Zé - AL
3.0 star property
Velas
9.6 out of 10, Exceptional, (7)
"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. "
United States
Susan
Casa do Zé - AL
Outdoor pool
A Casa do Ouvidor

A Casa do Ouvidor

A Casa do Ouvidor
4.0 star property
Sao Roque do Pico
9.8 out of 10, Exceptional, (29)
"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. "
Canada
Sébastien
A Casa do Ouvidor
Soundproofing, iron/ironing board, free WiFi, bed sheets
Pico Terrace

Pico Terrace

Pico Terrace
3.0 star property
Madalena
9.8 out of 10, Exceptional, (8)
"We had a good time in this comfortable place. "
Canada
Arianne
Pico Terrace
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
The price is HK$877
HK$912 total
includes taxes & fees
2 Jan - 3 Jan 2026
Aldeia das Adegas
Property grounds
Cliff-Top Ocean-Fronted Villa With Gardens And Private Pool

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

Cliff-Top Ocean-Fronted Villa With Gardens And Private Pool
Silveira, Lajes do Pico
9.8 out of 10, Exceptional, (49)
"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!"
United States
Kris S.
Cliff-Top Ocean-Fronted Villa With Gardens And Private Pool
Outdoor dining
New Family Home with a View of São Jorge Island – Ribeirinha

New Family Home with a View of São Jorge Island – Ribeirinha

New Family Home with a View of São Jorge Island – Ribeirinha
Ribeirinha
New Family Home with a View of São Jorge Island – Ribeirinha
Outdoor pool
Refúgio da Montanha

Refúgio da Montanha

Refúgio da Montanha
3.0 star property
Sao Roque do Pico
10.0 out of 10, Exceptional, (3)
"The view, the surroundings, the pool!!! The house is very convenient and has everything you need! "
United States
hilde F. J.
Refúgio da Montanha
Smart TV, DVD player, books
AtlanticWindow - Modern House, Stunning View

AtlanticWindow - Modern House, Stunning View

AtlanticWindow - Modern House, Stunning View
São Roque do Pico
10.0 out of 10, Exceptional, (49)
"The house was very comfortable for 4 adults and had everything needed for a great stay. The view is spectacular. Helena was very accommodating. I would recommend AtlanticWindow for anyone looking to stay on Pico for a few days. "
Portugal
Doyle B.
AtlanticWindow - Modern House, Stunning View
TV, fireplace
4 bedrooms & great view

4 bedrooms & great view

4 bedrooms & great view
Sao Roque do Pico, Azores
9.8 out of 10, Exceptional, (9)
"The check-in was a breeze and the house has everything you need to stay in and cook and there’s always a nice breeze to keep the house cool "
United States
Steven C.
4 bedrooms & great view
Exterior
Casa Céu D'Abraão - You can click to enlarge the photo

Casa Céu D'Abraão - You can click to enlarge the photo

Casa Céu D'Abraão - You can click to enlarge the photo
Lajes do Pico
8.8 out of 10, Excellent, (5)
"Lovely place, very beautiful and calm, also very clean. Isa is a very nice and extremely helpful host. Absolutely recommend to stay here!"
Austria
Lara Sophie S.
Casa Céu D'Abraão - You can click to enlarge the photo
Property grounds
Faidoca's Grandfather House - Four-Bedroom House

Faidoca's Grandfather House - Four-Bedroom House

Faidoca's Grandfather House - Four-Bedroom House
Calheta de Nesquim
10.0 out of 10, Exceptional, (20)
"It was a wonderful place and our host was a beautiful caring lady."
Canada
Liz S.
Faidoca's Grandfather House - Four-Bedroom House
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 Prainha Hotel Reviews

Hotel Caravelas

Hotel Caravelas

10/10 Excellent
"Great location and breakfast"
Tammie 1-night trip
Posted 8 days ago
Hotel Caravelas

Find out more about Prainha

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

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

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

Frequently asked questions

Can I find holiday rentals in Prainha?

Yes, there are holiday rentals close to the most popular sights in Prainha, or you can select a more secluded option if you're looking for a relaxing stay. Prainha is known for its seaside and restaurants.

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

Liiiving in A Ores - Ocean View House: This highly rated holiday home rental in Prainha offers a BBQ and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind. Some other homes for rent in Prainha include Pike Cliffs - Amazing view to S. Jorge and Casa da Atafona - Quinta da Ribeira da Urze.

How many holiday rentals will I find in Prainha?

Expedia has 52 holiday rentals for your stay in Prainha.

What can I see and do in Prainha?

Enjoy the area's cultural attractions such as Whaler’s Museum, or get outdoors into nature at a spot like São João Forest Reserve. Mount Pico and Azores Wine Company are a couple of places you'll find in the wider area.

What are holiday rentals like in Prainha?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Prainha. Holiday rentals feature amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family gatherings.