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Flight and Pet-friendly hotel deals in Pico Island

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

Adegas do Pico

CA $2,384

per person

Aug 3 - Aug 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Pico Island (PIX)

9/10 Wonderful! (39 reviews)

Beautiful house and fantastic host! Loved my time here!

Reviewed on Jun 9, 2026

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Pet-friendly Hotels in Pico Island

Pico Dreams - Sportfish

Rua do Laranjal, 9 A Sao Roque do Pico

25 min drive from Pico Island Vineyard Culture

Stay at this guesthouse in Sao Roque do Pico. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Convent of Sao Roque do Pico and A Buraca ...

9.2/10 Wonderful! (68 reviews)

"Pico Dreams is great! The room was spacious and clean. The staff was great. It is quiet and close enough to everything ( as long as you have a car). We also made use of the beautiful pool and the washing machine and clothes line"

Reviewed on Jun 28, 2026

Vinhas do Calhau

Porto do Calhau 42 Madalena Madalena

5 min drive from Pico Island Vineyard Culture

Book a stay at this family-friendly hotel in Madalena. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Pico Island Vineyard Culture and ...

9.6/10 Exceptional! (53 reviews)

"The location and apartment are simply perfect! The rooms were really clean and the breakfast was plentyfull. Staff (Isabel & Ana) was also very helpful and responsive. 100% recommend!"

Reviewed on Jun 25, 2026

Room-amazing Quadruple Room With Sea Vie

Sao Roque do Pico Azores

26 min drive from Pico Island Vineyard Culture

Stay at this guesthouse in Sao Roque do Pico. Popular attractions Convent of Sao Roque do Pico and A Buraca Winery are located nearby.

See all 381 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.