Pico Island Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

Photo by Brian Scrivner

Find your perfect Pico Island beach vacation

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 . 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

Hotel Caravelas

Hotel Caravelas

4 out of 5
Rua Conselheiro Terra Pinheiro, 3 Madalena
  • 4 min drive from Pico Island Vineyard Culture
Book a stay at this beach hotel in Madalena. Enjoy free WiFi, free parking, and room service. Popular attractions Museu do Vinho and Adega do Vulcão are located ...
7.8/10 Good! (216 reviews)
Spacious, clean, quite and amazing breakfast

Reviewed on Nov 4, 2025

Hotel Caravelas
Sara Village

Sara Village

3 out of 5
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 ...
8.2/10 Very Good! (58 reviews)
Exceeded expirations. Owner is beautiful, staff very helpful and customer oriented. On main hwy which is convenient but can be noisy. View is exceptional. Highly recommend!

Reviewed on Oct 14, 2025

Sara Village
Pocinhobay

Pocinhobay

4 out of 5
Pocinho Madalena
  • 26 min walk from Pico Island Vineyard Culture
Book a stay at this beach guesthouse in Madalena. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Pico Island Vineyard Culture and ...
9.2/10 Wonderful! (40 reviews)
A gem of a property - close enough to everything but far enough to enjoy the peacefulness of the island. Staff were helpful, polite, courteous and thoughtful. Highly recommend.

Reviewed on Jul 22, 2025

Pocinhobay
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.