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Pico Island Holiday Rentals

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Our top choices for Pico Island holiday rentals

1. Aldeia das Adegas

Aldeia das Adegas
4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (68 reviews)
"We had a great stay here."
United States
Nicholas
The price is NZ$248
includes taxes & fees
8 Sept - 9 Sept
Aldeia das Adegas

2. Aldeia dos Caldeirões

Aldeia dos Caldeirões
4.0 star property
Madalena
8.8 out of 10, Excellent, (3 reviews)
"The place is beautiful, in a great location, private and secluded, with nice amenities such as hot tubs, pool, wood BBQ. It looks just like the pictures and overall, we enjoyed our stay. But, - very limited hot water. Takes long to warm up and then only lasts 5 minutes. Not enough for 2 showers. We could only fill the amazing bath up a few inches before it got cold, so kind of useless. - lots of ants, and when we complained, we were told to deal with it ourselves - there was a birds nest...
Canada
Evan
The price is NZ$210
includes taxes & fees
2 Sept - 3 Sept
Aldeia dos Caldeirões

3. Silveira House

Silveira House
Lajes do Pico
The price is NZ$173
includes taxes & fees
16 Sept - 17 Sept
Silveira House

4. SKY MOUNTAIN & SEA SMS-AZORES

SKY MOUNTAIN & SEA SMS-AZORES
São Roque do Pico
2.0 out of 10, (1 review)
"Airline canceled our flight. I emailed the host i had no response. "
United States
Thomas M.
The price is NZ$515
includes taxes & fees
27 Aug - 28 Aug
SKY MOUNTAIN & SEA SMS-AZORES

5. Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
Lajes do Pico
The price is NZ$156
includes taxes & fees
4 Sept - 5 Sept
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

6. Apartment 'Valverdeapart' with Private Terrace and Wi-Fi

Apartment 'Valverdeapart' with Private Terrace and Wi-Fi
Madalena
The price is NZ$359
includes taxes & fees
6 Sept - 7 Sept
Apartment 'Valverdeapart' with Private Terrace and Wi-Fi

7. Casa do Jardim

Casa do Jardim
Santo Amaro
The price is NZ$403
includes taxes & fees
18 Sept - 19 Sept
Casa do Jardim

8. Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning

Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
Prainha
The price is NZ$673
includes taxes & fees
4 Sept - 5 Sept
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning

9. Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi
Lajido
The price is NZ$431
includes taxes & fees
5 Sept - 6 Sept
Holiday Home 'Adega Maciel' with Sea View, Private Terrace and Wi-Fi

10. Casa do Laureano

Casa do Laureano
Santo Amaro
Casa do Laureano

11. Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is NZ$465
includes taxes & fees
2 Sept - 3 Sept
Holiday Home 'Adega Pérola' with Wi-Fi

12. Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
Lajes do Pico
6.0 out of 10, (1 review)
"Pros: Die Ruhe, der Ausblick, der private Parkplatz, die schnelle Unterstützung durch die Ansprechperson, der Insektenschutz an Fenstern Cons: Schwierigkeit gehabt das Haus zu finden, da das einzige Schild am Haus selbst hängt und von der Straße aber nicht zu erkennen war; leichter Schimmel in der Dusche; penetranter Duft der Duftspender in Küche und Bad; Bettwäsche roch nicht sehr frisch"
Germany
Anonymous traveller
The price is NZ$431
includes taxes & fees
22 Aug - 23 Aug
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

13. Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace & Wi-Fi

Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace & Wi-Fi
Santo António SRP
The price is NZ$518
includes taxes & fees
4 Sept - 5 Sept
Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace & Wi-Fi

14. Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
Ribeiras
The price is NZ$527
includes taxes & fees
20 Sept - 21 Sept
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

15. Casa Baleia Laranja Ocean-Front

Casa Baleia Laranja Ocean-Front
Madalena
10.0 out of 10, Exceptional, (3 reviews)
"The location of the property was wonderful. We could hear the waves crashing throughout our stay. Thank you again "
United States
Sebastien B.
The price is NZ$880
includes taxes & fees
8 Sept - 9 Sept
Casa Baleia Laranja Ocean-Front

16. Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
Engrade
10.0 out of 10, Exceptional, (1 review)
"Pros: The house was recently renovated, everything was nice and clean, very kind host, peaceful place with view of the ocean and vineyards"
United States
Anonymous traveller
The price is NZ$551
includes taxes & fees
7 Sept - 8 Sept
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

17. Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
Pontas negras
7.0 out of 10, Good, (2 reviews)
"Nicley updated and clean but damp/musty smell. Location was good but required a drive to any attractions, restaurants, or markets. Balcony was nice but required access through the main bedroom. No communications on check-out procedures. Price was a bit high for what was offered."
United States
Eugene S.
The price is NZ$1,108
includes taxes & fees
1 Sept - 2 Sept
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

18. Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines

Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines
São Roque do Pico
The price is NZ$1,159
includes taxes & fees
20 Sept - 21 Sept
Pico Island Villas 22 - Ocean Front & UNESCO Heritage Century-Old Grapevines

19. Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi
Pontas Negras
The price is NZ$1,279
includes taxes & fees
1 Sept - 2 Sept
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

20. Bearsu Nature Almoxarife

Bearsu Nature Almoxarife
2.0 star property
Horta
8.6 out of 10, Excellent, (7 reviews)
"Nice camping near the sea"
Italy
Leonardo
The price is NZ$86
includes taxes & fees
19 Sept - 20 Sept
Bearsu Nature Almoxarife
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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Top Pico Island Hotel Reviews

Find out more about Pico Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pico Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pico Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pico Island. Seeing all the best attractions is bound to make you fall in love with Pico Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pico Island short-term rentals, that won’t be hard to do.