Pico Island Vacation Packages 2026 from $976

Photo by Brian Scrivner

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Pico Island vacation packages

Price found within the past 48 hours. Click for updated prices.

Sara Village

$976

per person

Oct 3 - Oct 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pico Island (PIX)

8.4/10 Very Good! (65 reviews)

We did not stay and cancellation was not accepted.

Reviewed on Aug 6, 2026

Adegas do Pico

$1,258

per person

Oct 3 - Oct 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pico Island (PIX)

9/10 Wonderful! (39 reviews)

Beautiful house and fantastic host! Loved my time here!

Reviewed on Jun 9, 2026

Areias da Prainha

$1,645

per person

Oct 19 - Oct 25

found 23 hours ago

Roundtrip flight included

Orlando (MCO) to Pico Island (PIX)

10/10 Exceptional! (3 reviews)

Lovely!

Reviewed on Jun 11, 2024

Aldeia da Fonte Hotel

$1,418

per person

Oct 3 - Oct 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pico Island (PIX)

8/10 Very Good! (1 review)

Fantastic room! Newly remodeled ocean view. Listening to ocean waves while falling asleep is amazing. Great breakfast and dinner.

Reviewed on Jul 29, 2026

Pico Dreams - Sportfish

$1,273

per person

Oct 19 - Oct 25

found 23 hours ago

Roundtrip flight included

Orlando (MCO) to Pico Island (PIX)

9.2/10 Wonderful! (70 reviews)

Great stay here! It was clean and quiet and they have all the amenities of home, even a washing machine and clothes line which is very helpful after hiking Pico Mountain

Reviewed on Jul 2, 2026

Don't see what you're looking for?

See all available trips from Des Moines to Pico Island

View all trips

Stay near popular Pico Island attractions

Mount Pico

9.2/10 (65 reviews)

Commune with nature and explore the great outdoors at Mount Pico during your travels in São Caetano. Discover the area's mountain views and sunrises.

See properties

Pico Island Vineyard Culture

9.0/10 (44 reviews)

You can enjoy a tasting or tour at Pico Island Vineyard Culture during your travels to Criação Velha. While you're in the area, stroll along the marina.

See properties

São João Forest Reserve

9.2/10 (21 reviews)

Explore the great outdoors at São João Forest Reserve, a lovely green space in São João.

See properties

Gruta das Torres

9.0/10 (26 reviews)

Explore the great outdoors at Gruta das Torres, a lovely green space in Criação Velha. While you're in the area, stroll along the marina.

See properties

Sao Roque Church

8.6/10 (10 reviews)

After visiting Sao Roque Church, make a plan to see the other sights and activities in Sao Roque do Pico. While you're in the area, stroll along the seaside.

See properties

Azores Wine Company

You can enjoy a tasting or tour at Azores Wine Company during your travels to Bandeiras.

See properties

Whaler’s Museum

8.4/10 (26 reviews)

You can spend time exploring the galleries in Whaler’s Museum during your travels in Lajes do Pico. While you're in the area, stroll along the seaside.

See properties

Caiado Lagoon

8.4/10 (14 reviews)

Explore the great outdoors at Caiado Lagoon, a lovely green space in Lajes do Pico. While you're in the area, stroll along the seaside.

See properties

What to do in Pico Island

Picture 10 for Activity Horta, Faial: University based Whale & Dolphin Expedition

Horta, Faial: Research Whale & Dolphin Expedition

$101

per adult

100% of travellers recommend

Happy Cows Buggy Tour

$344

per traveler

Whale and Dolphin Watching in Pico Island - Half Day

$93

per adult

See all activities in Pico Island

Pico Island Hotel Deals

Pico TERRAMAR & SPA

Rua Dr. Manuel de Arriaga Areia Larga Madalena Azores

$254 nightly

$264 total

Aug 27 - Aug 28

Total with taxes and fees

Hotel Caravelas

Rua Conselheiro Terra Pinheiro, 3 Madalena

$124 nightly

$129 total

Aug 31 - Sep 1

Total with taxes and fees

8/10 Very Good! (240 reviews)

"I have visited 5 of the 9 islands in the archipelago and this was by far the nicest and best hotel stay."

Reviewed on Aug 10, 2026

Azores Youth Hostels - Pico

Rua João Bento Lima Sao Roque do Pico

$67 nightly

$69 total

Sep 10 - Sep 11

Total with taxes and fees

8/10 Very Good! (44 reviews)

"L’emplacement, la vue sur la mer, le charme d’un vieil édifice patrimonial rénové, très propre, personnel vraiment accueillant, stationnement facile, un bon pdj assez simple mais convenable. Seul bémol au niveau de la plomberie de la salle de bain ch101 qui aurait besoin de rénovation car de petites ..."

Reviewed on Jun 14, 2026

See all 392 properties in Pico Island

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.