Pico Island Vacation Rentals from $81: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

Sao Roque do Pico

Nicholas

$78 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden table and bench in a garden with a hot tub and a glass door leading to a room.

2. Aldeia dos Caldeirões

Madalena

"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...

Evan

$84 nightly

Nov 23 - Nov 24

Total with taxes and fees

A rectangular pool with clear blue water, surrounded by a tiled deck.

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

Ribeiras

$191 nightly

Dec 1 - Dec 2

Total with taxes and fees

A spacious living area with a high wooden ceiling, a black leather sofa, and a dining area in the background.

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

Santo António SRP

$282 nightly

Nov 18 - Nov 19

Total with taxes and fees

A stone building with a red door, green shutters, and a balcony.

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

Pontas negras

Eugene S.

$378 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

Prainha

$334 nightly

Nov 18 - Nov 19

Total with taxes and fees

A poolside dining area with a view of the ocean, featuring burgers and fries on the table.

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

Lajes do Pico

$82 nightly

Dec 9 - Dec 10

Total with taxes and fees

A stone building with a stone wall, a window, and a door leading to an interior with a cow-patterned wall.

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

Lajido

$172 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Ribeirinha

Amélie T.

$344 nightly

Nov 23 - Nov 24

Total with taxes and fees

A modern living room with a wooden staircase, a sofa, a coffee table, and a dining area.

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

Pontas Negras

$552 nightly

Nov 23 - Nov 24

Total with taxes and fees

11. ValverdeApart - 1.7 km from the center of Madalena, Pico Island

Madalena

$154 nightly

Nov 23 - Nov 24

Total with taxes and fees

A stone-walled room with a white chair and table, a window, and a view of a landscape.

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

Lajes do Pico

Anonymous traveler

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.

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

São Roque do Pico

$643 nightly

Nov 24 - Nov 25

Total with taxes and fees

A compact kitchen with wooden cabinets, a built-in oven, and a dining area with a table and chairs.

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

Ribeirinha

$302 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

Cais do Galego

$168 nightly

Nov 13 - Nov 14

Total with taxes and fees

A modern room with wooden beams, a white sofa, a round table, and a view of the sea through a window.

16. Lofts Azul Pastel

Horta

Cathy

$63 nightly

Nov 18 - Nov 19

Total with taxes and fees

A modern interior with a large sliding glass door leading to a balcony, wooden beams on the ceiling, and a dark wall.

17. Porto Pim Bay

Horta

Joseph

$63 nightly

Nov 20 - Nov 21

Total with taxes and fees

A coastal view with a mountain in the background, a pier, and a clear sky.

18. Horta Bay

Horta

samuel

$63 nightly

Nov 14 - Nov 15

Total with taxes and fees

A modern room with a sofa, a bed, a small table, and a view of the outdoors.

19. Apartment 'Apartamento T2 Praia Do Almoxarife' with Sea View, Wi-Fi and Air Conditioning

Horta

Tajmohammed

$204 nightly

Nov 24 - Nov 25

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Pico Island Hotel Reviews

Pico Vineyards

10/10 Excellent

"Everything was top notch!!!"

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!"

My Bed in Pico

10/10 Excellent

"Débora est au top. A l'écoute elle nous a sur classé pour notre anniversaire de mariage, elle a fait tout ce qu'elle a pu pour nous satisfaire. Très jolie et grande chambre avec frigo, café, thé, eau et plein de petites attentions. Literie très bonne avec un grand lit double. Bravo pour la décoration de notre chambre des voyageurs. Merci pour tout."

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.

Explore a world of travel with Expedia

Expedia's Latest Trends

Hotels

Flights

Cars

Activities

Things to do in São Miguel Island

Packages

Vacation Rentals

Vacation Rental São Miguel Island

General

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Pico Island vacation rentals

1. Aldeia das Adegas

2. Aldeia dos Caldeirões

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

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

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

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

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

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

9. Pico Azores - Family house S. Jorge view

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

11. ValverdeApart - 1.7 km from the center of Madalena, Pico Island

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

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

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

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

16. Lofts Azul Pastel

17. Porto Pim Bay

18. Horta Bay

19. Apartment 'Apartamento T2 Praia Do Almoxarife' with Sea View, Wi-Fi and Air Conditioning

Find vacation rentals that suit your style

Top Pico Island Hotel Reviews

Pico Vineyards

Pico Dreams - Sportfish

Porto Velho Boutique Lodge

Hotel Caravelas

Vinhas do Calhau

Aldeia da Fonte Hotel

My Bed in Pico

AL Novavista by BPX

Blue Almance - T2 Apartment

Find out more about Pico Island

Explore a world of travel with Expedia

Expedia's Latest Trends

Go further with the Expedia app