Prainha Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Prainha vacation rentals

Aldeia das Adegas

Aldeia das Adegas
4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (64 reviews)
"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 CA $155
CA $162 total
includes taxes & fees
Feb 19 - Feb 20
Aldeia das Adegas

Vila Paim - Apart. Low

Vila Paim - Apart. Low
São Roque do Pico
10.0 out of 10, Exceptional, (1 review)
"Great getaway super quiet and very relaxing place."
United States
Joe F.
The price is CA $404
CA $619 total
includes taxes & fees
Feb 18 - Feb 19
Vila Paim - Apart. Low

Aldeia dos Caldeirões

Aldeia dos Caldeirões
3.5 star property
Madalena
The price is CA $149
CA $155 total
includes taxes & fees
Feb 19 - Feb 20
Aldeia dos Caldeirões

Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
São Jorge
10.0 out of 10, Exceptional, (4 reviews)
"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 CA $336
CA $396 total
includes taxes & fees
Feb 18 - Feb 19
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba
São Jorge
The price is CA $299
CA $339 total
includes taxes & fees
Feb 20 - Feb 21
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

Panoramic Ocean Views from your Private Varand

Panoramic Ocean Views from your Private Varand
São Roque do Pico
The price is CA $200
CA $253 total
includes taxes & fees
Feb 19 - Feb 20
Panoramic Ocean Views from your Private Varand

Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is CA $133
CA $232 total
includes taxes & fees
Feb 21 - Feb 22
Holiday Home 'Adega Pérola' with Wi-Fi

Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
São Jorge
10.0 out of 10, Exceptional, (1 review)
"serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso."
Portugal
Pedro E.
The price is CA $315
CA $357 total
includes taxes & fees
Feb 18 - Feb 19
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

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 CA $194
CA $330 total
includes taxes & fees
Mar 14 - Mar 15
Casa Baleia Laranja Ocean-Front

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
The price is CA $145
CA $275 total
includes taxes & fees
Feb 18 - Feb 19
Very well equipped apartment in the center of São Roque do Pico

Casa dos Felicias

Casa dos Felicias
São Roque do Pico
10.0 out of 10, Exceptional, (1 review)
"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 CA $121
CA $247 total
includes taxes & fees
Feb 18 - Feb 19
Casa dos Felicias

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
The price is CA $503
CA $572 total
includes taxes & fees
Feb 19 - Feb 20
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

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 CA $591
CA $660 total
includes taxes & fees
Feb 19 - Feb 20
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

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

Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
Ribeiras
The price is CA $319
CA $319 total
includes taxes & fees
Feb 19 - Feb 20
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

Vila Paim - Apart. DELUX

Vila Paim - Apart. DELUX
São Roque do Pico
The price is CA $808
CA $1,078 total
includes taxes & fees
Mar 17 - Mar 18
Vila Paim - Apart. DELUX

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 CA $248
CA $248 total
includes taxes & fees
Feb 18 - Feb 19
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

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 CA $355
CA $355 total
includes taxes & fees
Feb 19 - Feb 20
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Silveira House

Silveira House
Lajes do Pico
The price is CA $73
CA $142 total
includes taxes & fees
Mar 1 - Mar 2
Silveira House

Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
Calheta
The price is CA $229
CA $269 total
includes taxes & fees
Feb 18 - Feb 19
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
São Jorge
The price is CA $207
CA $236 total
includes taxes & fees
Feb 19 - Feb 20
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Prainha Hotel Reviews

Find out more about Prainha

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

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

Frequently asked questions

Can I find vacation rentals in Prainha?

Yes, we give you a choice of vacation rentals near well known points of interest in Prainha, or you can select a more secluded option if you're looking for relaxation. Prainha is known for its seaside and restaurants.

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

Pike Cliffs - Amazing view to S. Jorge: This highly rated vacation home rental in Prainha is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Prainha?

Expedia has 47 vacation 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 Pico da Esperanca are a couple of places you'll find in the larger area.

What are vacation rentals like in Prainha?

Vacation rentals are private accommodations you can reserve for a short or long stay in Prainha. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.