Pico Island Vacation Rentals

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Our top choices for Pico Island vacation rentals

Aldeia das Adegas

Aldeia das Adegas
4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (64 reviews)
"Wonderful stay. Beautiful units with great hospitality"
United States
Adam
$121 nightly
The price is $126
May 19 - May 20
Total with taxes and fees
Aldeia das Adegas

Aldeia dos Caldeirões

Aldeia dos Caldeirões
4.0 star property
Madalena
10.0 out of 10, Exceptional, (1 review)
"Superbe petite maison accueillante "
Canada
Eric
$117 nightly
The price is $122
May 21 - May 22
Total with taxes and fees
Aldeia dos Caldeirões

Apartment 'Valverdeapart' with Private Terrace and Wi-Fi

Apartment 'Valverdeapart' with Private Terrace and Wi-Fi
Madalena
$186 nightly
The price is $186
May 18 - May 19
Total with taxes and fees
Apartment 'Valverdeapart' with Private Terrace 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
$171 nightly
The price is $171
May 22 - May 23
Total with taxes and fees
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
Lajes do Pico
$100 nightly
The price is $100
Jun 10 - Jun 11
Total with taxes and fees
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool 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 traveler
$313 nightly
The price is $313
May 17 - May 18
Total with taxes and fees
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
$163 nightly
The price is $163
May 18 - May 19
Total with taxes and fees
Holiday Home 'Adega Pérola' with Wi-Fi

Silveira House

Silveira House
Lajes do Pico
$103 nightly
The price is $103
May 19 - May 20
Total with taxes and fees
Silveira House

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
$242 nightly
The price is $242
May 24 - May 25
Total with taxes and fees
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and 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
$562 nightly
The price is $562
May 17 - May 18
Total with taxes and fees
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace and Wi-Fi

Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace and Wi-Fi
Santo António SRP
$221 nightly
The price is $231
May 31 - Jun 1
Total with taxes and fees
Apartment 'Vista Da Baía - Casa Do Aniceto' 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
Ribeiras
$205 nightly
The price is $205
May 28 - May 29
Total with taxes and fees
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines

Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines
São Roque do Pico
$700 nightly
The price is $700
May 16 - May 17
Total with taxes and fees
Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines

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.
$537 nightly
The price is $537
Jun 5 - Jun 6
Total with taxes and fees
Casa Baleia Laranja Ocean-Front

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
$712 nightly
The price is $712
May 22 - May 23
Total with taxes and fees
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

Bearsu Nature Almoxarife

Bearsu Nature Almoxarife
2.0 star property
Horta
8.8 out of 10, Excellent, (6 reviews)
"Nice camping near the sea"
Italy
Leonardo
$46 nightly
The price is $48
May 22 - May 23
Total with taxes and fees
Bearsu Nature Almoxarife

Lofts Azul Pastel

Lofts Azul Pastel
4.0 star property
Horta
9.8 out of 10, Exceptional, (33 reviews)
"Beautiful stay and wonderful staff!"
United States
Cathy
$97 nightly
The price is $101
May 16 - May 17
Total with taxes and fees
Lofts Azul Pastel

Horta Bay

Horta Bay
3.5 star property
Horta
10.0 out of 10, Exceptional, (6 reviews)
"The best place I ever been in faial island I love it ❤️❤️❤️❤️❤️👌"
United States
samuel
$115 nightly
The price is $120
May 16 - May 17
Total with taxes and fees
Horta Bay

Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
Topo Calheta São Jorge Açores
$167 nightly
The price is $167
May 24 - May 25
Total with taxes and fees
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

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.
$329 nightly
The price is $341
May 24 - May 25
Total with taxes and fees
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
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 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 $122 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.