Calheta Vacation Rentals

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Sep 30 - Oct 1
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Oct 1 - Oct 2
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Oct 3 - Oct 5
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Oct 10 - Oct 12

Vacation Rentals in Calheta

Matilde's House, in the paradise Fajã de São João
Fridge, microwave, oven, stovetop

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

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

$150 nightly
The price is $150
Oct 6 - Oct 7
Total with taxes and fees
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
Herdade das Hortênsias
Beach

Herdade das Hortênsias

10.0 out of 10, Exceptional, (1)
"Ruhig gelegen mit genügend Platz."
$133 nightly
The price is $133
Oct 5 - Oct 6
Total with taxes and fees
Herdade das Hortênsias
Aldeia das Adegas
Exterior

Aldeia das Adegas

4.0 star property
9.4 out of 10, Exceptional, (61)
"Beautiful and quiet, excellent amenities, comfortable and private, great location in São Roque. Highly recommend. "
$141 nightly
The price is $146
Oct 3 - Oct 4
Total with taxes and fees
Aldeia das Adegas
Casa do Zé - AL
View from property

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

Adegas do Pico

4.0 star property
9.0 out of 10, Wonderful, (38)
"Very nice rural property "
Adegas do Pico
Casas da Junqueira
House (Água) | Living room | Flat-screen TV

Casas da Junqueira

4.0 star property
9.2 out of 10, Wonderful, (11)
"We Love place and location Everything is perfectly peaceful Not so many restaurants in this area though And mosquitoes were there 😉"
Casas da Junqueira
A Casa do Ouvidor
Outdoor pool

A Casa do Ouvidor

4.0 star property
9.8 out of 10, Exceptional, (29)
"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
AtlanticWindow - Modern House, Stunning View
Smart TV, DVD player, books

AtlanticWindow - Modern House, Stunning View

10.0 out of 10, Exceptional, (48)
"Staying at this beautiful home with amazing views has made our vacation one we will never forget! We highly recommend staying her when you vacation in Pico. It will be one of the highlights of your trip"
AtlanticWindow - Modern House, Stunning View
Faidoca's Grandfather House - Four-Bedroom House
Property grounds

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
Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar
1 bedroom, iron/ironing board, WiFi, bed sheets

Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar

Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar
Pike Cliffs - Amazing view to S. Jorge
Interior

Pike Cliffs - Amazing view to S. Jorge

9.6 out of 10, Exceptional, (7)
"Great views and good mid island location. House had all amenities needed. We had beautiful weather and enjoyed the food, wine and friendly Puco people. Good memories had by all."
Pike Cliffs - Amazing view to S. Jorge
4 bedrooms & great view
TV, fireplace

4 bedrooms & great view

9.8 out of 10, Exceptional, (9)
"Friendly, very well situated, very calm and safe neighbourhood."
4 bedrooms & great view
Laura's Cottage AL
Fridge, microwave, oven, stovetop

Laura's Cottage AL

Laura's Cottage AL
Casa Céu D'Abraão - You can click to enlarge the photo
Exterior

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

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

10.0 out of 10, Exceptional, (23)
"Wonderful little house with amazing views and terrific host. Perfect for couples get away. You will love the true Pico Island experience here. "
Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".
Casa da Esquila 2
Microwave, oven, stovetop, dishwasher

Casa da Esquila 2

Casa da Esquila 2
Adega Velha holiday home, next to the sea and mountains, ideal for couples
Terrace/patio

Adega Velha holiday home, next to the sea and mountains, ideal for couples

9.6 out of 10, Exceptional, (20)
"Adega Velha was a perfect place for the two of us while we explored Pico. Although it is a very small house, it was impeccably clean, comfortable and beautifully appointed. Everything you could imagine needing was there, tidily tucked in to its own appointed space. The view from the house is exceptional, and we found the quiet location so charming and restful. Fatima and her husband were extremely gracious, even leaving us a gift basket upon our arrival. I highly recommend this guest house and...
Adega Velha holiday home, next to the sea and mountains, ideal for couples
Houses In Pico
Front of property

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
Vacation Home "Casas Dos Vinagreiros - Umbelina" with Sea View, Private Terrace & Wi-Fi
Fridge, microwave, oven, stovetop

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

$292 nightly
The price is $292
Oct 31 - Nov 1
Total with taxes and fees
Vacation Home "Casas Dos Vinagreiros - Umbelina" with Sea View, Private Terrace & Wi-Fi
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.
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Top Calheta Hotel Reviews

35th Atlantic View

35th Atlantic View

10/10 Excellent
"It would be great if the room just had a closet to store your clothes away. We had to use the couch to leave our lugage and clothes."
Jose Moises 2-night trip
Posted 3 days ago
35th Atlantic View

Find out more about Calheta

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 $133 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar: You might want to consider this vacation home rental near Calheta, which is by the ocean and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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?

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.