Calheta Vacation Rentals from $146: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Calheta?

Pico Island Villas 20 · Private Pool, Sea & Pico View : You might want to consider this vacation home rental near Calheta, which offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

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Our top choices for Calheta vacation rentals

1. Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

São Jorge

David B.

$326 nightly

Sep 4 - Sep 5

Total with taxes and fees

2. Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

São Jorge

Pedro E.

$316 nightly

Sep 1 - Sep 2

Total with taxes and fees

3. Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

São Jorge

$231 nightly

Sep 4 - Sep 5

Total with taxes and fees

4. Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Calheta

$246 nightly

Sep 2 - Sep 3

Total with taxes and fees

5. Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

São Jorge

$299 nightly

Sep 1 - Sep 2

Total with taxes and fees

6. Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

Topo Calheta São Jorge Açores

$187 nightly

Aug 22 - Aug 23

Total with taxes and fees

7. Casa da Petra – Our Casa is your Casa

Urzelina

$520 nightly

Aug 23 - Aug 24

Total with taxes and fees

8. Carpe Diem Apartment

Urzelina

$157 nightly

Sep 1 - Sep 2

Total with taxes and fees

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Top Calheta Hotel Reviews

São Jorge Garden

10/10 Excellent

"WE LOVED THE HOTEL POOL. AC WORKED WELL IN THE ROOMS"

Quinta dos Mistérios

10/10 Excellent

"The stay at this property was awesome!! The historic property and structure are very unique and provide a wonderful stay. The interior and grounds are really beautiful and we feel lucky to have stayed here. The rooms have everything you need and are clean, quiet, safe and comfortable. Breakfast was really good, too. The owner and her concierge are extremely nice and helpful and I look forward to staying here again in the future. "

Casa d'Avó Guesthouse

10/10 Excellent

"Our room had a patio with sliding doors overlooking the ocean! Gorgeous!!! There is a central kitchen that guests can use to make meals and lots of great places to sit. The staff are amazing. They help to call taxis, provide laundry service and any other help you may need. The owner came by regularly to check on how things were going and was easy to access."

Azores Youth Hostels - Pico

8/10 Good

"L’emplacement, la vue sur la mer, le charme d’un vieil édifice patrimonial rénové, très propre, personnel vraiment accueillant, stationnement facile, un bon pdj assez simple mais convenable. Seul bémol au niveau de la plomberie de la salle de bain ch101 qui aurait besoin de rénovation car de petites odeurs."

A Casa do Ouvidor

10/10 Excellent

"A spacious space with a lovely view. We were looking for a place to relax on a quieter island, and this set the perfect tone for our time on Pico. The villa is in a lovely location - less than 2k from a bakery, coffee shops, and a small grocery store if you want nearby options. Or you're 15 minutes from Madelena for more options. You're right off the ring road, and there are several beautiful miradoros nearby - or enjoy the views from your window or the back yard. The kitchen was well-equipped, and there are lots of spaces to lounge inside and out. We were excited to use the space as a home base and space to recharge for active days around the island and visits to Faial. It was exactly that, and we are recommending spot to friends."

Find out more about Calheta

Everything you need to know about Calheta vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Calheta vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Calheta vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Calheta vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Calheta. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Calheta in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $146 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Calheta rentals

At Expedia, we put the best Calheta vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Calheta rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Calheta vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Calheta. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Calheta?

Yes, there are vacation rentals near popular sights in Calheta, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Calheta?

Pico Island Villas 20 · Private Pool, Sea & Pico View: You might want to consider this vacation home rental near Calheta, which offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals will I find in Calheta?

Choose from 13 Expedia vacation rentals in Calheta for a memorable vacation.

What can I see and do in Calheta?

Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge and Cascata do Cruzal are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Fajã dos Cubres and Pico da Esperanca.

What are vacation rentals like in Calheta?

Vacation rentals are privately owned properties you can reserve for several days or more in Calheta. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.

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Check prices for these dates

Our top choices for Calheta vacation rentals

1. Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

2. Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

3. Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

4. Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

5. Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

6. Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

7. Casa da Petra – Our Casa is your Casa

8. Carpe Diem Apartment

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

10. Aldeia das Adegas

11. Casa da Terra Alta

12. Casa do Laureano

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

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

15. Carpe Noctem Apartment

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

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

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

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

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

Top Calheta Hotel Reviews

São Jorge Garden

Kuanza Nature Experience

Quinta dos Mistérios

Cabanas da Viscondessa

Casa d'Avó Guesthouse

Pico Dreams - Sportfish

Azores Youth Hostels - Pico

Adegas do Pico

A Casa do Ouvidor

Find out more about Calheta

Frequently asked questions

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