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Pico Island Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Pico Island vacation rentals

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
$113 nightly
The price is $118
Jan 21 - Jan 22, 2026
Total with taxes and fees
Aldeia das Adegas
Outdoor pool, sun loungers
Aldeia dos Caldeirões

Aldeia dos Caldeirões

Aldeia dos Caldeirões
3.5 star property
Madalena
$91 nightly
The price is $95
Jan 9 - Jan 10, 2026
Total with taxes and fees
Aldeia dos Caldeirões
Exterior
Casa dos Felicias

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.
$180 nightly
The price is $180
Dec 29 - Dec 30
Total with taxes and fees
Casa dos Felicias
Property grounds
Casa Baleia Laranja Ocean-Front

Casa Baleia Laranja Ocean-Front

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.
$264 nightly
The price is $264
Dec 29 - Dec 30
Total with taxes and fees
Casa Baleia Laranja Ocean-Front
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

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.
$216 nightly
The price is $216
Jan 20 - Jan 21, 2026
Total with taxes and fees
Very well equipped apartment in the center of São Roque do Pico
Outdoor dining
Vacation Home "Adega Do Portinho Velho" with Balcony & 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)
"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
$259 nightly
The price is $259
Dec 29 - Dec 30
Total with taxes and fees
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
Fridge, microwave, oven, stovetop
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

Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
Pontas negras
$322 nightly
The price is $322
Dec 29 - Dec 30
Total with taxes and fees
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
2 bedrooms, iron/ironing board, WiFi, bed sheets
Adega do Mirante

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
$180 nightly
The price is $180
Dec 29 - Dec 30
Total with taxes and fees
Adega do Mirante
Property grounds
Vila Paim - Apart. Low

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.
$145 nightly
The price is $180
Dec 29 - Dec 30
Total with taxes and fees
Vila Paim - Apart. Low
TV
Vila Paim - Apart. DELUX

Vila Paim - Apart. DELUX

Vila Paim - Apart. DELUX
São Roque do Pico
$254 nightly
The price is $278
Dec 28 - Dec 29
Total with taxes and fees
Vila Paim - Apart. DELUX
Property grounds
Amazing One Bedroom Apartment with Sea View

Amazing One Bedroom Apartment with Sea View

Amazing One Bedroom Apartment with Sea View
São Roque do Pico
$94 nightly
The price is $94
Dec 28 - Dec 29
Total with taxes and fees
Amazing One Bedroom Apartment with Sea View
Microwave, oven, stovetop, dishwasher
Panoramic Ocean Views from your Private Varand

Panoramic Ocean Views from your Private Varand

Panoramic Ocean Views from your Private Varand
São Roque do Pico
$178 nightly
The price is $184
Dec 28 - Dec 29
Total with taxes and fees
Panoramic Ocean Views from your Private Varand
Exterior detail
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

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
$181 nightly
The price is $181
Dec 28 - Dec 29
Total with taxes and fees
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi
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

Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
Lajes do Pico
$57 nightly
The price is $57
Dec 29 - Dec 30
Total with taxes and fees
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
TV
Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
$175 nightly
The price is $175
Dec 28 - Dec 29
Total with taxes and fees
Holiday Home 'Adega Pérola' with Wi-Fi
Private kitchen
Silveira House

Silveira House

Silveira House
Lajes do Pico
$104 nightly
The price is $104
Jan 20 - Jan 21, 2026
Total with taxes and fees
Silveira House
TV, DVD player
Vacation Home "Retiro Dos Cabritos" with Sea View and Private Terrace

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

Vacation Home "Retiro Dos Cabritos" with Sea View and Private Terrace
São Mateus
$241 nightly
The price is $241
Dec 28 - Dec 29
Total with taxes and fees
Vacation Home "Retiro Dos Cabritos" with Sea View and Private Terrace
Pool
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

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

Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
2.0 star property
Ribeiras
$207 nightly
The price is $207
Dec 28 - Dec 29
Total with taxes and fees
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
Fridge, microwave, oven, stovetop
Vacation Home "Dos Vinagreiros - Guilherme" 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
$421 nightly
The price is $421
Dec 29 - Dec 30
Total with taxes and fees
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & 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

Beautiful One Bedroom Apartment near the sea in Sao Roque do Pico
São Roque do Pico
$94 nightly
The price is $94
Dec 28 - Dec 29
Total with taxes and fees
Beautiful One Bedroom Apartment near the sea in Sao Roque do Pico
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

Hotel Caravelas

Hotel Caravelas

10/10 Excellent
"Great location and breakfast"
Tammie 1-night trip
Posted 2 weeks ago
Hotel Caravelas

Find out more about Pico Island

Everything you need to know about Pico Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pico Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pico Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pico Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $95 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pico Island rentals

At Expedia, we put the best Pico Island vacation 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 vacation.

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.

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