Calheta Holiday Rentals from €72: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Calheta has to offer?

Matilde's House, in the paradise Fajã de São João : This highly rated holiday home rental in Calheta is located by the ocean, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Calheta holiday rentals

A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

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

São Jorge

includes taxes & fees

2 Nov - 3 Nov

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

Calheta

includes taxes & fees

2 Nov - 3 Nov

A coastal landscape with a stone wall, a grassy area, and a view of the ocean and mountains.

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

São Jorge

David B.

includes taxes & fees

2 Nov - 3 Nov

4. Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

São Jorge

Kimberly

includes taxes & fees

2 Nov - 3 Nov

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

São Jorge

Pedro E.

includes taxes & fees

2 Nov - 3 Nov

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

São Jorge

includes taxes & fees

2 Nov - 3 Nov

A stone building with a red roof, a paved pathway, and a stone wall with a red railing.

7. Aldeia das Adegas

Sao Roque do Pico

Nicholas

includes taxes & fees

1 Nov - 2 Nov

A stone building with a tiled roof, a staircase leading to a seating area with chairs, and lush greenery surrounding the property.

8. Casa do Laureano

Santo Amaro

includes taxes & fees

17 Oct - 18 Oct

View all properties

Find holiday rentals that suit your style

Apartments

Condos

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Calheta Hotel Reviews

Casa do Zé - AL

10/10 Excellent

"C’est la dernière maison au bout du chemin. La terrasse sur la photo est en haut à gauche sur le chemin de pierre , non annexée à la maison. La vue est incroyable."

Azores Youth Hostels - Pico

10/10 Excellent

"The hostel is such a lovely place, very good located and the staff was really helpful, wherever you need they are always there to help you. Very nice and peaceful place. 100% recommended. The unic thing that I missed was a kitchen so you can cook your own food. But there are very nice local restaurants beside the hostel."

Quinta da Magnólia

10/10 Excellent

"The property is situated in a beautiful location and very close to the airport. The staff was super helpful and kind. Breakfast was delicious. Room was big with great view. I would advise to bring your own toiletries. It only has shower cap and soap. I was prepared so it wasn't a big deal."

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

10/10 Excellent

"Luca was an excellent host! We so appreciated his timely responses and baked bread. He has a talent for hospitality. The view was amazing! I can’t imagine being any closer to the Atlantic Ocean. The walk to Faga do Santa Cristo and the sweet restaurant therein was delightful. The bed was a bit hard for my taste, but it was easy to pile up the comforters from the bunk beds. This was a special place to celebrate life with my family. Obrigado!!!"

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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Calheta holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Calheta holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Calheta holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Calheta holiday rentals we have selected for you start as low as €72 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Calheta rentals

At Expedia, we put the best Calheta holiday 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 holiday.

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 holiday rentals in Calheta?

Yes, there are holiday rentals close to the most popular sights in Calheta, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Calheta has to offer?

Matilde's House, in the paradise Fajã de São João: This highly rated holiday home rental in Calheta is located by the ocean, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Calheta?

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

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 wider area, you’ll find Fajã dos Cubres and Pico da Esperanca.

What are holiday rentals like in Calheta?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Calheta. Holiday rentals feature extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family trip.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Calheta holiday rentals

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

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

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

4. Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

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