Calheta Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Calheta

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

The price is AU$235
includes taxes & fees
30 Sept - 1 Oct
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

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

9.0 out of 10, Wonderful, (4)
"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."
Matilde's House, in the paradise Fajã de São João

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

The price is AU$498
includes taxes & fees
16 Sept - 17 Sept
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

Herdade das Hortênsias

The price is AU$209
includes taxes & fees
21 Sept - 22 Sept
Herdade das Hortênsias

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

The price is AU$476
includes taxes & fees
26 Sept - 27 Sept
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

Fajã da Caldeira House - AL

10.0 out of 10, Exceptional, (1)
"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...
Fajã da Caldeira House - AL

Aldeia das Adegas

4.0 star property
9.4 out of 10, Exceptional, (60)
"Beautiful and quiet, excellent amenities, comfortable and private, great location in São Roque. Highly recommend. "
The price is AU$223
includes taxes & fees
21 Sept - 22 Sept
Aldeia das Adegas

Casa do Zé - AL

3.0 star property
9.2 out of 10, Wonderful, (5)
"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. "
Casa do Zé - AL

Cantinho do Mar - Holiday Home

9.4 out of 10, Exceptional, (10)
"Adorable apartment!"
Cantinho do Mar - Holiday Home

AtlanticWindow - Modern House, Stunning View

10.0 out of 10, Exceptional, (48)
"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."
AtlanticWindow - Modern House, Stunning View

Pike Cliffs - Amazing view to S. Jorge

9.8 out of 10, Exceptional, (6)
"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."
Pike Cliffs - Amazing view to S. Jorge

Adegas do Pico

4.0 star property
9.0 out of 10, Wonderful, (38)
"Very nice rural property "
Adegas do Pico

4 bedrooms & great view

9.8 out of 10, Exceptional, (9)
"Friendly, very well situated, very calm and safe neighbourhood."
4 bedrooms & great view

Faidoca's Grandfather House - Four-Bedroom House

10.0 out of 10, Exceptional, (20)
"It was a wonderful place and our host was a beautiful caring lady."
Faidoca's Grandfather House - Four-Bedroom House

Cantinho das Buganvillias

4.0 star property
9.6 out of 10, Exceptional, (35)
"Beautiful property overlooking Velas harbor…don’t hesitate to book!"
Cantinho das Buganvillias

Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".

10.0 out of 10, Exceptional, (22)
"Perfect"
Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".

A Casa do Ouvidor

4.0 star property
9.8 out of 10, Exceptional, (28)
"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. "
A Casa do Ouvidor

Houses In Pico

3.0 star property
8.6 out of 10, Excellent, (13)
"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."
Houses In Pico

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

8.6 out of 10, Excellent, (4)
"Lovely place, very beautiful and calm, also very clean. Isa is a very nice and extremely helpful host. Absolutely recommend to stay here!"
Casa Céu D'Abraão - You can click to enlarge the photo

Casa Baía da Feteira

10.0 out of 10, Exceptional, (1)
"We enjoyed the three days we stayed at Casa Baía de Feteira. The house was well stocked with towels and kitchen supplies and the welcome basket was a nice touch. Note Google maps does not take you to the driveway when using the “directions” feature within the vrbo app but rather a nearby location. This was easily and quickly corrected by a note to the host. "
Casa Baía da Feteira
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Calheta Hotel Reviews

Find out more about Calheta

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, 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 favourite 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 depend 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 AU$209 per night. Entering your travel dates in the search wizard might find you 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 selection of games, 1 hot tub 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 12 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 Velas Marina and Igreja de Sao Jorge.

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.