Prainha Holiday Rentals

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Holiday Rentals in Prainha

Apartment in Sao Roque do Pico

4.0 star property
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 AU$175
includes taxes & fees
2 Jan - 3 Jan 2026
Aldeia das Adegas

Holiday Home in São Roque do Pico

10.0 out of 10, Exceptional, (1)
"Great getaway super quiet and very relaxing place."
United States
Joe F.
Vila Paim - Apart. Low

Holiday Home in 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 AU$271
includes taxes & fees
9 Dec - 10 Dec
Casa dos Felicias

Holiday Home in Lajes do Pico

The price is AU$157
includes taxes & fees
9 Dec - 10 Dec
Silveira House

Holiday Home in 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 AU$271
includes taxes & fees
20 Dec - 21 Dec
Adega do Mirante

Villa in Lajes do Pico

The price is AU$86
includes taxes & fees
11 Dec - 12 Dec
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Villa in Madalena

3.0 star property
The price is AU$158
includes taxes & fees
9 Dec - 10 Dec
Aldeia dos Caldeirões

Apartment in São Roque do Pico

The price is AU$140
includes taxes & fees
9 Dec - 10 Dec
Amazing One Bedroom Apartment with Sea View

Holiday Home in Cais do Galego

The price is AU$251
includes taxes & fees
12 Dec - 13 Dec
Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home in São Jorge

10.0 out of 10, Exceptional, (1)
"serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso."
Portugal
Pedro E.
The price is AU$384
includes taxes & fees
9 Dec - 10 Dec
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

Holiday Home in 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 traveller
The price is AU$385
includes taxes & fees
10 Dec - 11 Dec
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Apartment in São Roque do Pico

The price is AU$140
includes taxes & fees
9 Dec - 10 Dec
Beautiful One Bedroom Apartment near the sea in Sao Roque do Pico

Holiday Home in 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 AU$325
includes taxes & fees
23 Dec - 24 Dec
Very well equipped apartment in the center of São Roque do Pico

Holiday Home in São Jorge

10.0 out of 10, Exceptional, (4)
"location, location, location plus the thoughtful design, adaptive reuse of structures, and the evident and abundant care of ownership and staff all added up to bliss for our group perhaps not for everyone, but the adventure of getting there and provisioning one’s stay can make for an even more satisfying stay."
United States
David B.
The price is AU$428
includes taxes & fees
9 Dec - 10 Dec
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

Holiday Home in Ribeiras

2.0 star property
The price is AU$308
includes taxes & fees
9 Dec - 10 Dec
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

Holiday Home in São Roque do Pico

The price is AU$277
includes taxes & fees
9 Dec - 10 Dec
Panoramic Ocean Views from your Private Varand

Holiday Home in São Jorge

The price is AU$365
includes taxes & fees
9 Dec - 10 Dec
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

Holiday Home in São Jorge

The price is AU$259
includes taxes & fees
12 Dec - 13 Dec
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

Holiday Home in Calheta

The price is AU$294
includes taxes & fees
9 Dec - 10 Dec
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Villa in Madalena

10.0 out of 10, Exceptional, (3)
"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 AU$833
includes taxes & fees
18 Dec - 19 Dec
Casa Baleia Laranja Ocean-Front
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

Find out more about Prainha

Everything you need to know about Prainha holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Prainha holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Prainha holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Prainha holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Prainha. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Prainha holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Prainha holiday rentals we have selected for you start as low as AU$175 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Prainha rentals

At Expedia, we put the best Prainha holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Prainha rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Prainha holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Prainha. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 51 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 Igreja de Sao Jorge 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.