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Pico Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Pico Island vacation rentals

A stone building with a red roof, a paved pathway, and a stone wall with a red railing.

1. Aldeia das Adegas

Aldeia das Adegas
4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (70 reviews)
"We had a great stay here."
United States
Nicholas
$78 nightly
The price is $81
Nov 1 - Nov 2
Total with taxes and fees
Aldeia das Adegas
A wooden table and bench in a garden with a hot tub and a glass door leading to a room.

2. Aldeia dos Caldeirões

Aldeia dos Caldeirões
4.0 star property
Madalena
9.0 out of 10, Wonderful, (4 reviews)
"The place is beautiful, in a great location, private and secluded, with nice amenities such as hot tubs, pool, wood BBQ. It looks just like the pictures and overall, we enjoyed our stay. But, - very limited hot water. Takes long to warm up and then only lasts 5 minutes. Not enough for 2 showers. We could only fill the amazing bath up a few inches before it got cold, so kind of useless. - lots of ants, and when we complained, we were told to deal with it ourselves - there was a birds nest...
Canada
Evan
$84 nightly
The price is $87
Oct 15 - Oct 16
Total with taxes and fees
Aldeia dos Caldeirões
A poolside dining area with a view of the ocean, featuring burgers and fries on the table.

3. 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
$82 nightly
The price is $82
Nov 3 - Nov 4
Total with taxes and fees
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
A stone building with a tiled roof, a staircase leading to a seating area with chairs, and lush greenery surrounding the property.

4. Casa do Laureano

Casa do Laureano
Santo Amaro
$137 nightly
The price is $137
Oct 25 - Oct 26
Total with taxes and fees
Casa do Laureano
A stone-walled room with a white chair and table, a window, and a view of a landscape.

5. 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
6.0 out of 10, (1 review)
"Pros: Die Ruhe, der Ausblick, der private Parkplatz, die schnelle Unterstützung durch die Ansprechperson, der Insektenschutz an Fenstern Cons: Schwierigkeit gehabt das Haus zu finden, da das einzige Schild am Haus selbst hängt und von der Straße aber nicht zu erkennen war; leichter Schimmel in der Dusche; penetranter Duft der Duftspender in Küche und Bad; Bettwäsche roch nicht sehr frisch"
Germany
Anonymous traveler
$122 nightly
The price is $122
Oct 31 - Nov 1
Total with taxes and fees
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
A stone building with a wooden deck, a table, and chairs.

6. Casa da Terra Alta

Casa da Terra Alta
Santo Amaro
10.0 out of 10, Exceptional, (1 review)
"We had great stay, a fabulous place to sit and enjoy the view in the evening. The house was comfortable and had everything we needed. Bed linens and towels were of good quality, not always the case in some places we have stayed in. Erica was a lovely host; you could tell she cared very much for the house and garden. We would recommend Highland Homes to anyone going to Pico Island!"
Canada
Anonymous traveler
$204 nightly
The price is $204
Oct 17 - Oct 18
Total with taxes and fees
Casa da Terra Alta
A bedroom with two beds, a chair, a coat rack, and a window with curtains.

7. Apartment 'Valverdeapart' with Private Terrace and Wi-Fi

Apartment 'Valverdeapart' with Private Terrace and Wi-Fi
Madalena
8.0 out of 10, Very good, (1 review)
"."
United States
Miranda C.
$163 nightly
The price is $163
Nov 3 - Nov 4
Total with taxes and fees
Apartment 'Valverdeapart' with Private Terrace and Wi-Fi
A white building with grey trim, a stone wall, and a small garden with various plants.

8. Silveira House

Silveira House
Lajes do Pico
$98 nightly
The price is $98
Oct 27 - Oct 28
Total with taxes and fees
Silveira House
A covered outdoor seating area with a table and chairs, overlooking a scenic view of the sea and green landscape.

9. Pico Azores - Family house S. Jorge view

Pico Azores - Family house S. Jorge view
Ribeirinha
10.0 out of 10, Exceptional, (1 review)
"Nous étions 2 familles et avons passé une superbe semaine. Les chambres sont bien divisées et il y avait le nécessaire pour notre séjour. La maison est très propre et très belle."
United States
Amélie T.
$344 nightly
The price is $344
Nov 3 - Nov 4
Total with taxes and fees
Pico Azores - Family house S. Jorge view
A stone building with a stone wall, a window, and a door leading to an interior with a cow-patterned wall.

10. 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
$171 nightly
The price is $171
Oct 17 - Oct 18
Total with taxes and fees
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi
A spacious living area with a high wooden ceiling, a black leather sofa, and a dining area in the background.

11. Vista da Baía - Casa do Aniceto Apartment with Sea View, Private Terrace & Wi-Fi

Vista da Baía - Casa do Aniceto Apartment with Sea View, Private Terrace & Wi-Fi
Santo António SRP
$282 nightly
The price is $282
Oct 20 - Oct 21
Total with taxes and fees
Vista da Baía - Casa do Aniceto Apartment with Sea View, Private Terrace & Wi-Fi
A rectangular pool with clear blue water, surrounded by a tiled deck.

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

Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
Ribeiras
$196 nightly
The price is $196
Oct 20 - Oct 21
Total with taxes and fees
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
A stone house with a red roof and orange shutters, featuring a patio with lounge chairs and a hammock.

13. Casa Baleia Laranja Ocean-Front

Casa Baleia Laranja Ocean-Front
Madalena
10.0 out of 10, Exceptional, (5 reviews)
"The location of the property was wonderful. We could hear the waves crashing throughout our stay. Thank you again "
United States
Sebastien B.
$390 nightly
The price is $390
Oct 17 - Oct 18
Total with taxes and fees
Casa Baleia Laranja Ocean-Front
A stone wall with a wooden fence.

14. Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning

Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
Prainha
$384 nightly
The price is $384
Oct 14 - Oct 15
Total with taxes and fees
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
A room with a wooden ceiling, a bed, a desk with a lamp, a fan, and a window.

15. Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
$167 nightly
The price is $167
Oct 17 - Oct 18
Total with taxes and fees
Holiday Home 'Adega Pérola' with Wi-Fi
A stone building with a red door, green shutters, and a balcony.

16. 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
7.0 out of 10, Good, (2 reviews)
"Nicley updated and clean but damp/musty smell. Location was good but required a drive to any attractions, restaurants, or markets. Balcony was nice but required access through the main bedroom. No communications on check-out procedures. Price was a bit high for what was offered."
United States
Eugene S.
$377 nightly
The price is $377
Oct 14 - Oct 15
Total with taxes and fees
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
A compact kitchen with wooden beams, a built-in oven, a microwave, and a refrigerator.

17. Apartment 'Ribeirinha 94' with Sea View and Wi-Fi

Apartment 'Ribeirinha 94' with Sea View and Wi-Fi
Ribeirinha
$302 nightly
The price is $302
Oct 20 - Oct 21
Total with taxes and fees
Apartment 'Ribeirinha 94' with Sea View and Wi-Fi
A hotel room with a bed, a view through a door, and a balcony.

18. 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
$245 nightly
The price is $245
Nov 3 - Nov 4
Total with taxes and fees
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
A modern living room with a wooden staircase, a sofa, a coffee table, and a dining area.

19. 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
$552 nightly
The price is $552
Oct 14 - Oct 15
Total with taxes and fees
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi
A room with a view of the sea through large windows, a dining table with a bowl and a glass, and a hanging light fixture.

20. 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
$676 nightly
The price is $676
Oct 20 - Oct 21
Total with taxes and fees
Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines
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

Porto Velho Boutique Lodge

Porto Velho Boutique Lodge

10/10 Excellent
"This place was amazing! It’s right by the water, with the ferry literally at your doorstep. Waking up each morning was great, especially with the waterfront views of Faial. They have coffee available 24/7 and pastries in the morning, plus a few local shops nearby for food, delicious may I add! I stayed in the basement and it was great. The place was very clean, had a kitchen with plates and dishes, and I absolutely loved the terrace. Yes, you can hear the church bells since the place is directly across from a church, and you can hear people if they’re loud upstairs, but that’s pretty normal for a basement. I’m not a light sleeper, and I slept like a baby here. The room did get a bit humid at night, but they had an AC unit, which was perfect. The location is central to everything in Madalena. The grocery store is about a 5-minute walk, and you’re within walking distance of pretty much anything you need. It’s also only about 10 minutes from the airport. The staff were incredibly kind and gave great recommendations for places to see. Entry and exit were easy, they had secure places for your bags in the room which is important to me. I cannot praise this place enough. If you need somewhere to stay in Madalena, I honestly wouldn’t recommend looking anywhere else. The location, the views, the staff, and the place itself were all perfect. I would absolutely stay here again!"
Tania 1-night trip
Posted 3 days ago
Porto Velho Boutique Lodge

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 $81 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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