Calheta Vacation Rentals from $162: Search Short-Term Rentals

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

Matilde's House, in the paradise Fajã de São João : Visitors give good reviews to this Calheta vacation home rental, which is located by the ocean and has a selection of games, a hot tub, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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Vacation Rentals in Calheta

$162 nightly

Sep 1 - Sep 2

Total includes taxes and fees

"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."

$321 nightly

Sep 19 - Sep 20

Total includes taxes and fees

$454 nightly

Sep 1 - Sep 2

Total includes taxes and fees

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

$321 nightly

Sep 19 - Sep 20

Total includes taxes and fees

"Wonderful stay. Beautiful units with great hospitality"

$168 nightly

Sep 14 - Sep 15

Total includes taxes and fees

"Adorable apartment!"

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

"Adorable local cottage in a very small town. We stayed in the 2 bedroom apartment on the second floor. Neighbors gave us a walking tour and showed us their garden and taught us history of the area. "

Adega da Atafona, 1 Bedroom, Ocean View | Terrace/patio

"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."

"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."

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

"We loved our stay and immediately fell in love with the house. It had all the amenities you would need and more and the views were absolutely astounding. It was definitely the best part of our stay while visiting the Azores."

Indoor pool, outdoor pool, pool umbrellas, sun loungers

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

"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. "

"Pleasant surprise with gift basket and heater on at arrival! We never saw the host, but very accommodating online. Well equipped and nice location. On the downside, the beds and pillows are very hard."

"We only stayed for one night, but the house is very well located and clean."

"Lovely place, very beautiful and calm, also very clean. Isa is a very nice and extremely helpful host. Absolutely recommend to stay here!"

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Top Calheta Hotel Reviews

Casa d'Avó Guesthouse

10/10 Excellent

"Ben arredata; pulitissima e personale gentilissimo"

Pico Dreams - Sportfish

10/10 Excellent

"We had a truly lovely stay at this charming guesthouse. The owner and her husband are without a doubt the sweetest people we met during our trip. On the morning of our departure, her husband even offered, completely on his own initiative, to drive us to the ferry. That level of kindness and hospitality is rare these days and deserves to be recognized. The place itself is spotless, cozy, and thoughtfully arranged. There’s a warm, welcoming atmosphere throughout, with a beautiful common area where you can relax and unwind after a day of exploring. You can tell that a lot of care goes into maintaining the property, it feels like a home, not just a rental. One of the highlights is the stunning view of Pico from the house. Waking up to that view each morning was a gift. Whether you’re enjoying your coffee outside or just soaking in the peace and quiet, the setting is perfect. Everything was well-organized, from check-in to check-out. The room was comfortable, the linens were fresh, and all the small details were in place. It’s clear that the owners take great pride in what they do and it shows. We would return in a heartbeat. Highly recommended if you’re looking for a genuine, heartwarming stay in the Azores. "

Sara Village

8/10 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! :)"

Kuanza Nature Experience

10/10 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. "

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 $162 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.

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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?

Matilde's House, in the paradise Fajã de São João: Visitors give good reviews to this Calheta vacation home rental, which is located by the ocean and has a selection of games, a hot tub, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Calheta?

Choose from 12 Expedia vacation rentals in Calheta for a memorable vacation.

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 larger area, you’ll find Velas Marina and Igreja de Sao Jorge.

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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Calheta Vacation Rentals

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Vacation Rentals in Calheta

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

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

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

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

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

Aldeia das Adegas

Cantinho do Mar - Holiday Home

4 bedrooms & great view

Casa do Zé - AL

Adegas do Pico

Casa das Pereiras - Rural Tourism T2

Pike Cliffs - Amazing view to S. Jorge

Faidoca's Grandfather House - Four-Bedroom House

AtlanticWindow - Modern House, Stunning View

Cantinho das Buganvillias

Férias de Sonho na Ilha do Pico, nos Açores

A Casa do Ouvidor

Houses In Pico

House Santana Pico Island Garden

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

Top Calheta Hotel Reviews

Casa d'Avó Guesthouse

Quinta dos Mistérios

Pico Dreams - Sportfish

São Jorge Garden

Azores Youth Hostels - São Jorge

Quinta da Magnólia

Cabanas da Viscondessa

Sara Village

Kuanza Nature Experience

Find out more about Calheta

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Frequently asked questions