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Pico Island Holiday Rentals

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Holiday Rentals in Pico Island

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 AU$177
includes taxes & fees
2 Jan - 3 Jan 2026
Aldeia das Adegas

Aldeia dos Caldeirões

3.0 star property
Madalena
The price is AU$159
includes taxes & fees
3 Dec - 4 Dec
Aldeia dos Caldeirões

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 AU$274
includes taxes & fees
4 Dec - 5 Dec
Casa dos Felicias

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 AU$274
includes taxes & fees
3 Dec - 4 Dec
Vila Paim - Apart. Low

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 AU$274
includes taxes & fees
20 Dec - 21 Dec
Adega do Mirante

Holiday Home 'Adega Pérola' with Wi-Fi

Cais do Galego
The price is AU$254
includes taxes & fees
5 Dec - 6 Dec
Holiday Home 'Adega Pérola' with Wi-Fi

Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Lajes do Pico
The price is AU$86
includes taxes & fees
3 Dec - 4 Dec
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

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 AU$328
includes taxes & fees
23 Dec - 24 Dec
Very well equipped apartment in the center of São Roque do Pico

Silveira House

Lajes do Pico
The price is AU$159
includes taxes & fees
3 Dec - 4 Dec
Silveira House

Amazing One Bedroom Apartment with Sea View

São Roque do Pico
The price is AU$142
includes taxes & fees
5 Dec - 6 Dec
Amazing One Bedroom Apartment with Sea View

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 traveller
The price is AU$389
includes taxes & fees
3 Dec - 4 Dec
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Panoramic Ocean Views from your Private Varand

São Roque do Pico
The price is AU$280
includes taxes & fees
3 Dec - 4 Dec
Panoramic Ocean Views from your Private Varand

Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

Lajido
The price is AU$272
includes taxes & fees
3 Dec - 4 Dec
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

Casa Baleia Laranja Ocean-Front

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$841
includes taxes & fees
18 Dec - 19 Dec
Casa Baleia Laranja Ocean-Front

Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

Pontas negras
The price is AU$484
includes taxes & fees
3 Dec - 4 Dec
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

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

São Roque do Pico
The price is AU$142
includes taxes & fees
3 Dec - 4 Dec
Beautiful One Bedroom Apartment near the sea in Sao Roque do Pico

Vacation Home "Retiro Dos Cabritos" with Sea View and Private Terrace

São Mateus
The price is AU$363
includes taxes & fees
3 Dec - 4 Dec
Vacation Home "Retiro Dos Cabritos" with Sea View and Private Terrace

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

2.0 star property
Ribeiras
The price is AU$311
includes taxes & fees
9 Dec - 10 Dec
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

Pontas Negras
The price is AU$633
includes taxes & fees
14 Dec - 15 Dec
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

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
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 Pico Island Hotel Reviews

Find out more about Pico Island

Everything you need to know about Pico Island 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 Pico Island 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 Pico Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pico Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pico Island. 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 Pico Island 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 Pico Island holiday rentals we have selected for you start as low as AU$159 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pico Island rentals

At Expedia, we put the best Pico Island 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 Pico Island 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 Pico Island 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 Pico Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.