Pico Island Beach Vacations 2026

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

Top Beach vacation packages in Pico Island

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

Adegas do Pico

$1,252

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Pico Island (PIX)

9/10 Wonderful! (40 reviews)

Wonderful location as a home base to explore the island. Very clean, super helpful staff, and the view was amazing!

Reviewed on Aug 22, 2026

A Casa do Ouvidor

$1,400

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Pico Island (PIX)

9.6/10 Exceptional! (33 reviews)

There is no hottub at this property! We were really disappointed to see this when we arrived as it was one of the main reasons we booked here. The property need to update their expedia profile but please note there hasnt been a hottub there in a while. Otherwise, beautiful view and a nice stay at the property. A bit rough around the edges in places but perfectly adequate for our 4 night stay

Reviewed on Jun 9, 2026

Don't see what you're looking for?

See all available trips from Columbus to Pico Island

View all trips

3 Night Beach vacations in Pico Island

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

Adegas do Pico

$790

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pico Island (PIX)

9/10 Wonderful! (40 reviews)

Wonderful location as a home base to explore the island. Very clean, super helpful staff, and the view was amazing!

Reviewed on Aug 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Pico Island

View all trips

How do I book the best Pico Island beach vacation packages?

Life’s a beach when you dive into our brilliant Pico Island beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Pico Island?

A rental steps from the shore creates an amazingly affordable Pico Island beach vacation. Seaside sojourns during low season start from $790. Prices and availability are subject to change. Additional terms may apply.

When should I book a Pico Island beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Pico Island?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Pico Island beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Pico Island vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Pico Island beach vacation deals?

Sort your search results by deals to delight in amazing Pico Island beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Pico Island beach trip with free cancellation and/or flexible dates?

Just like the Pico Island tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Pico Island beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Pico Island. (OK, maybe not that last part.)

Top Beach Pico Island Hotels

Aldeia da Fonte Hotel

Caminho Da Fonte Silveira Lajes do Pico

35 min drive from Pico Island Vineyard Culture

Book a stay at this beach hotel in Lajes do Pico. Enjoy free WiFi, free parking, and room service. Popular attractions Whaler’s Museum and Cabeço do Ferrobo ...

8/10 Very Good! (5 reviews)

"Personnel très accueillant Très bon service Chambre très confortable"

Reviewed on Sep 27, 2026

Hotel Caravelas

Rua Conselheiro Terra Pinheiro, 3 Madalena

29 min walk from Pico Island Vineyard Culture

Book a stay at this beach hotel in Madalena. Enjoy free WiFi, free parking, and room service. Popular attractions Adega Cooperativa Vitivinícola da Ilha do Pico ...

8/10 Very Good! (250 reviews)

"Location next to ferry is perfect, rooms clean great breakfast. 100%"

Reviewed on Sep 29, 2026

Sara Village

Estrada Regional Nº1 Nº20 Sao Roque do Pico Azorea

26 min drive from Pico Island Vineyard Culture

Book a stay at this beach country house in Sao Roque do Pico. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Convent of Sao Roque ...

8.4/10 Very Good! (66 reviews)

"We did not stay and cancellation was not accepted."

Reviewed on Aug 6, 2026

See all 394 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.