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Pico Island Vacation Rentals

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Our top choices for Pico Island vacation rentals

Villa in Madalena

Pico Terrace
3.0 star property
9.8 out of 10, Exceptional, (8)
"We had a good time in this comfortable place. "
Canada
Arianne
Pico Terrace
9.8 out of 10, Exceptional, (49)
"We had such a relaxing stay at this beautiful home. My two kids loved the pool and the location next to the natural pools was amazing. Highly recommend!"
United States
Kris S.
Cliff-Top Ocean-Fronted Villa With Gardens And Private Pool

Apartment in Sao Roque do Pico

Aldeia das Adegas
4.0 star property
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 $117
Jan 2 - Jan 3, 2026
Total with taxes and fees
Aldeia das Adegas

Villa in Sao Roque do Pico

A Casa do Ouvidor
4.0 star property
9.8 out of 10, Exceptional, (29)
"Asan was a great host. Quiet place, very roomy and clean, the view is amazing. Every thing was in place to enjoy a confortable stay. "
Canada
Sébastien
A Casa do Ouvidor

Cottage in Sao Roque do Pico

Adegas do Pico
4.0 star property
9.0 out of 10, Wonderful, (38)
"Very nice rural property "
United States
Mario
Adegas do Pico

Vacation Home in São Roque do Pico

AtlanticWindow - Modern House, Stunning View
10.0 out of 10, Exceptional, (49)
"The house was very comfortable for 4 adults and had everything needed for a great stay. The view is spectacular. Helena was very accommodating. I would recommend AtlanticWindow for anyone looking to stay on Pico for a few days. "
Portugal
Doyle B.
AtlanticWindow - Modern House, Stunning View

Vacation Home in Prainha de Cima

Pike Cliffs - Amazing view to S. Jorge
9.6 out of 10, Exceptional, (8)
"We stayed at Pike Cliffs in July. The house is lovely and suitable for 4-6 people. We really like the views, and were able to reach Francisco when we got lost getting to the place. Thank you Francisco!"
Canada
A C.
Pike Cliffs - Amazing view to S. Jorge

Cottage in Sao Roque do Pico

Refúgio da Montanha
3.0 star property
10.0 out of 10, Exceptional, (3)
"The view, the surroundings, the pool!!! The house is very convenient and has everything you need! "
United States
hilde F. J.
Refúgio da Montanha
8.8 out of 10, Excellent, (5)
"Lovely place, very beautiful and calm, also very clean. Isa is a very nice and extremely helpful host. Absolutely recommend to stay here!"
Austria
Lara Sophie S.
Casa Céu D'Abraão - You can click to enlarge the photo

Vacation Home in São Roque do Pico

Panoramic Ocean Views from your Private Varand
$178 nightly
The price is $184
Dec 16 - Dec 17
Total with taxes and fees
Panoramic Ocean Views from your Private Varand

Villa in Madalena

Aldeia dos Caldeirões
3.5 star property
$99 nightly
The price is $103
Dec 19 - Dec 20
Total with taxes and fees
Aldeia dos Caldeirões

Vacation Home in Santo Amaro, Sao Roque, Ilha do Pico, Azores

Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".
10.0 out of 10, Exceptional, (24)
"Wonderful little house with amazing views and terrific host. Perfect for couples get away. You will love the true Pico Island experience here. "
United States
Austin
Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".
New Family Home with a View of São Jorge Island – Ribeirinha
9.8 out of 10, Exceptional, (21)
"Adega Velha was a perfect place for the two of us while we explored Pico. Although it is a very small house, it was impeccably clean, comfortable and beautifully appointed. Everything you could imagine needing was there, tidily tucked in to its own appointed space. The view from the house is exceptional, and we found the quiet location so charming and restful. Fatima and her husband were extremely gracious, even leaving us a gift basket upon our arrival. I highly recommend this guest house and...
Portugal
Seward O.
Adega Velha holiday home, next to the sea and mountains, ideal for couples

Villa in Sao Roque do Pico, Azores

4 bedrooms & great view
9.8 out of 10, Exceptional, (9)
"The check-in was a breeze and the house has everything you need to stay in and cook and there’s always a nice breeze to keep the house cool "
United States
Steven C.
4 bedrooms & great view

Cottage in Sao Roque do Pico

Houses In Pico
3.0 star property
8.6 out of 10, Excellent, (13)
"Pleasant surprise with gift basket and heater on at arrival! We never saw the host, but very accommodating online. Well equipped and nice location. On the downside, the beds and pillows are very hard."
Norway
Vibeke
Houses In Pico
9.4 out of 10, Exceptional, (6)
"Très bon accueil, grand appartement Très bien équipé avec tous les produits d'entretien disponibles. "
France
PATRICIA
Calm and rest combined with well-being with great views of the mountain and sea

Apartment in Sao Roque do Pico

Casas da Junqueira
4.0 star property
9.2 out of 10, Wonderful, (12)
"A clean modern apartment. Bed was comfortable with nice sheets and pillows. Kitchen had basic cooking utensils but unfortunately not have basic items for cooking like salt, pepper, sugar, oil. Nice welcome basket of goodies was much appreciated."
Canada
Lorne
Casas da Junqueira

Vacation Home in Calheta de Nesquim

Faidoca's Grandfather House - Four-Bedroom House
10.0 out of 10, Exceptional, (20)
"It was a wonderful place and our host was a beautiful caring lady."
Canada
Liz S.
Faidoca's Grandfather House - Four-Bedroom House

Vacation Home in Ribeira de Urze

Casa da Atafona - Quinta da Ribeira da Urze
10.0 out of 10, Exceptional, (1)
"Wir konnten hier eine sehr entspannte Ferienwoche genießen. Das Haus ist geräumig, luftig, sehr sauber. Die Vermieterin Salomé ist super nett und hilfreich."
Germany
Ina M.
Casa da Atafona - Quinta da Ribeira da Urze
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 $103 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.