Pico Island Luxury Vacations 2026

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Top Luxury vacation packages in Pico Island

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

Casa do Comendador

$929

per person

Sep 19 - Sep 22

found 14 hours ago

Roundtrip flight included

New York (NYC) to Pico Island (PIX)

8.6/10 Excellent! (29 reviews)

The air was very damp and smelled like mold. There was indeed some black mold on the shower curtain and on the window curtain. Everything felt slightly damp in the room including our pillows. It was therefore extremely uncomfortable and hard to sleep. We woke up in the morning feeling nausea presumably because of the disgusting air. There was also a door to the outside that rattled loudly every time a gust of wind blew which also made it hard to sleep. Overall I would recommend finding different accommodations if you can. It may have just been a problem with this one room though

Reviewed on May 3, 2024

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 1 day 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

A Casa do Ouvidor

$1,036

per person

Sep 19 - Sep 22

found 14 hours ago

Roundtrip flight included

New York (NYC) to Pico Island (PIX)

9.6/10 Exceptional! (32 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

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4 Night Luxury vacations in Pico Island

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

Sara Village

$997

per person

Sep 19 - Sep 22

found 14 hours ago

Roundtrip flight included

New York (NYC) 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

$1,248

per person

Sep 14 - Sep 17

found 9 hours ago

Roundtrip flight included

New York (NYC) to Pico Island (PIX)

9/10 Wonderful! (39 reviews)

Beautiful house and fantastic host! Loved my time here!

Reviewed on Jun 9, 2026

Aldeia da Fonte Hotel

$1,116

per person

Sep 19 - Sep 22

found 14 hours ago

Roundtrip flight included

New York (NYC) 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

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See all available trips from Columbus to Pico Island

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What can I expect from a luxury Pico Island vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Pico Island vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Pico Island?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Pico Island luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $929. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Pico Island?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Pico Island with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Pico Island?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Pico Island with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Pico Island with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.