Calheta Holiday Rentals from €150: Search Short-Term Rentals

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Holiday Rentals in Calheta

"serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso."

"location, location, location plus the thoughtful design, adaptive reuse of structures, and the evident and abundant care of ownership and staff all added up to bliss for our group perhaps not for everyone, but the adventure of getting there and provisioning one’s stay can make for an even more satisfying stay."

"Haus ist etwas dunkel, aber ansonsten sehr gut eingerichtet und sauber. Blick von der Terrasse aufs Meer und auf die Insel Pico. Wer Katzen mag, ist hier sehr gut aufgehoben."

includes taxes & fees

23 Jun - 24 Jun

"A fajã da Caldeira de Santo Cristo é um dos lugares de visita obrigatório em S. Jorge. Embora não tenha acesso de carro, existem dois trilhos que permitem o acesso ao lugar. Fizemos o trilho mais pequeno e demorámos aproximadamente 1 hora (levávamos crianças connosco). Alternativamente, este trilho pode ser feito com moto4. Vários habitantes locais fornecem esse serviço aos turistas para facilitar a entrada e saída da fajã. O nosso anfitrião (o Miguel), também se disponiblizou para nos facilitar...

"Very unique property. Great view. Loved the layout of property. For additional cost provided breakfast basket each day. Town has a well stocked grocery store nearby. Very picturesque village with a wonderful wine bar."

"Wonderful stay. Beautiful units with great hospitality"

includes taxes & fees

8 Jul - 9 Jul

"Asan was a great host. Quiet place, very roomy and clean, the view is amazing. Every thing was in place to enjoy a confortable stay. "

"We had a very peaceful and enjoyable stay, using the house as a base to climb Mt Pico, enjoy a whale watch and a wine tour. The host was very helpful with advice and helped arrange the wine tour and driver. The view out the back is beyond gorgeous and it’s a perfect deck to eat all your meals."

"The location was beautiful and the host was very friendly. The apartment was clean and well stocked; however, we booked this location to sleep and to shower and both experiences were sub par. The bed is so hard, it offers little comfort after climbing Mt. Pico. The shower set up is odd, splashing water all over the toilet and provided toilet paper. There was no a/c as advertised and we couldn't locate the washer; however, we didn't look hard. All in all the place was nice, but the bed was the...

"L'appartamento ha un potenziale enorme, se solo fosse gestita come si dovrebbe Ho prenotato ad aprile per 4 giorni ad agosto...ho contattato l'host 3 giorni prima di arrivare ma non mi ha risposto...il giorno dopo l'ho contattata con wattsapp e dopo vari messaggi e telefonate sono riuscita ad avere risposta per l'orario del check-in La casa e' nolto bella e il posto e' favoloso, immerso nei vigneti"

Indoor pool, outdoor pool, pool umbrellas, pool loungers

"Beautiful property overlooking Velas harbor…don’t hesitate to book!"

"We Love place and location Everything is perfectly peaceful Not so many restaurants in this area though And mosquitoes were there 😉"

On the beach, sun-loungers, beach towels

"It was a wonderful place and our host was a beautiful caring lady."

"Friendly, very well situated, very calm and safe neighbourhood."

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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 €150 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.

Recent reviews of Calheta properties

5/5 Excellent

"Beautifully maintained historic property, the owner is very hospitable. The breakfast is is all you need to start your day."

A verified traveller stayed at Quinta dos Mistérios

Posted 4 days ago

4/5 Good

"We were warmly welcomed by Miguel, the owner/manager of the place. We experienced a slight inconvenience with our room at arrival, but Miguel quickly offered us a solution, which was suitable and much appreciated. The view from the terrace was incredible! This is related to the town and not to the lodging, but for dining options, at the time of the year that we went (early June) there were not much choices. But overall, a good experience! :)"

A verified traveller stayed at Sara Village

Posted 2 weeks ago

5/5 Excellent

"I had a great stay at this hotel. The room was comfortable and clean, and everything was well-maintained. The breakfast was absolutely perfect—fresh, delicious, and with a good variety of options to choose from. The staff were very friendly, attentive, and always ready to help, which made the experience even more enjoyable. I would definitely recommend this hotel and look forward to staying here again."

A verified traveller stayed at São Jorge Garden

Posted 1 month ago

5/5 Excellent

"This property is in a spectacular location overlooking the magnificent Atlantic Ocean. You have to coordinate the resorts ATV transportation but it's we'll with the effort. This is a perfect place to escape so stay at least a few days if not more. You should stop at the grocery store and be fully stocked for meals although you're greeted with homemade bread, local cheese and the owners produced wine. "

A verified traveller stayed at Kuanza Nature Experience

Posted 2 months ago

5/5 Excellent

Wonderful stay in Urzelina

"Nice area to sit outside, well stocked kitchen, each room has a cabinet for items, basket of fruit from owner’s garden and lovely cake was on one of the tables for guests to enjoy. Diana works very hard keeping the place clean and is always available if have any questions. Short walk to two excellent local restaurants, small but well stocked supermarket and the Trilho Ecologico da Urzelina (TEU), a beautiful 3 KM coast path. "

A verified traveller stayed at Casa d'Avó Guesthouse

Posted 6 months ago

5/5 Excellent

"Kind people operating it. The property has a great view to the Pico Mountain, there are multiple houses lined up on a small street. It's a very peaceful vibe. It's within walking distance (an a beautiful walk - nice village with flowers, and fruits) to a cafe/bakery, a couple of restaurants, and a nice natural pool for swimming."

A verified traveller from Maywood stayed at Aldeia das Adegas

Posted 11 months ago

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?

Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista): This highly rated holiday home rental in Calheta is located by the ocean, and has an outdoor pool, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals will I find in Calheta?

Choose from 11 Expedia holiday rentals in Calheta for a memorable holiday.

What can I see and do in Calheta?

While you're exploring the area, Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge and Pico da Esperanca are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Caiado Lagoon and Velas Marina.

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.

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Holiday Rentals in Calheta

Check prices for these dates

Holiday Rentals in Calheta

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

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

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

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

Matilde's House, in the paradise Fajã de São João

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

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

Fajã da Caldeira House - AL

Adegas do Pico

Aldeia das Adegas

A Casa do Ouvidor

Pike Cliffs - Amazing view to S. Jorge

Casa Céu D'Abraão - You can click to enlarge the photo

Cantinho do Avô - Pico Island - Prainha, São Roque do Pico

Cantinho das Buganvillias

Casa das Pereiras - Rural Tourism T2

Casas da Junqueira

Faidoca's Grandfather House - Four-Bedroom House

Férias de Sonho na Ilha do Pico, nos Açores

4 bedrooms & great view

Find out more about Calheta

Recent reviews of Calheta properties

Quinta dos Mistérios

Sara Village

São Jorge Garden

Kuanza Nature Experience

Pico Dreams - Sportfish

35th Atlantic View

Casa d'Avó Guesthouse

Aldeia das Adegas

Azores Youth Hostels - Pico

Frequently asked questions