Search Vacation Homes in Calheta

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 148 Vacation Homes in Calheta with updated reviews, rates, and availability.

AtlanticWindow - Modern House, Stunning View

10.0 out of 10, Exceptional, (41)
"Absolutely stunning property & views! Stay was fantastic all around."
AtlanticWindow - Modern House, Stunning View

Pike Cliffs - Amazing view to S. Jorge

10.0 out of 10, Exceptional, (3)
"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

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

10.0 out of 10, Exceptional, (18)
"Very good! Everthing was wonderful"
Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".

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

3.4 out of 10, (3)
"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"
Cantinho do Avô - Pico Island - Prainha, São Roque do Pico

Casa da Esquila 2

Casa da Esquila 2

PICO Hollidays Rentals- Mountain and sea view for families or groups

10.0 out of 10, Exceptional, (11)
"Adelina was the most gracious and friendly host! Supplying us with incredible fruit and eggs from her gardens and chickens. The house had spectacular views of Sao Jorge and had tons of room for a family of 6. It also had a well appointed kitchen. Loved the location. A great stay. "
PICO Hollidays Rentals- Mountain and sea view for families or groups

Faidoca's Grandfather House - Four-Bedroom House

10.0 out of 10, Exceptional, (19)
"It was a wonderful place and our host was a beautiful caring lady."
Faidoca's Grandfather House - Four-Bedroom House

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

10.0 out of 10, Exceptional, (2)
"Isa was so amazing with communication and helping me set up any needs that I had for my trip. There was a welcome basket with bread and cheese and tea and coffee and water which was so much appreciated. A beautiful setting on their banana farm and close to an amazing restaurant and nice hiking. I love that the property has a bathtub for after a long day of hiking. Outdoor patio and barbecue we're a lovely place to end the day as well. I can't recommend this property more for a quiet place on...
Casa Céu D'Abraão - You can click to enlarge the photo

Quinta do Lago

Quinta do Lago

Great Tranquility Holiday Home

10.0 out of 10, Exceptional, (1)
"This place is a treasure. I highly recommend staying here. The hosts are amazing people and treat you like family. "
Great Tranquility Holiday Home

Casa da TerraltaView Pico Island Superb View over the São Jorge Azores Canal

9.2 out of 10, Wonderful, (5)
"A five star cottage for the scenery but you are entitled to expect much more confort when you pay more than 200 euros per night, especially when you are 5 or six. Big windows with no shutters + uncomfortable mattresses... The living room is quite small for a family since the garden furniture is stored inside (at least it was during our stay). Last but not least, some basic stuff was missing to cook and wash. Once again, too expensive for the level of service. Still, in spite of all that, we...
Casa da TerraltaView Pico Island Superb View over the São Jorge Azores Canal

House Santana Pico Island Garden

9.6 out of 10, Exceptional, (5)
"We only stayed for one night, but the house is very well located and clean."
House Santana Pico Island Garden

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

The price is AED 1,761
AED 1,939 total
includes taxes & fees
3 May - 4 May
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

Casa da Avó - Quinta da Ribeira da Urze

10.0 out of 10, Exceptional, (2)
"Nice large rental property in rural Prainha de Cima. Host was very nice and accommodating. Clean apartment with everything you need for comfortable stay. Day trips are easy to Horta or Velas on the ferries. Recommended. Great value."
Casa da Avó - Quinta da Ribeira da Urze

Holiday house Santa Bárbara for 1 - 4 persons with 2 bedrooms - Holiday house

9.0 out of 10, Wonderful, (2)
Holiday house Santa Bárbara for 1 - 4 persons with 2 bedrooms - Holiday house

Adega do Mirante

8.0 out of 10, Very Good, (1)
"The basic necessities are provided; beds are comfortable and the place is clean. Need to Whatsapp owner to get information to get onto the property because messaging in Portugese otherwise. Property said air conditioning but the air conditioning was broken. It was cool enough though so not a problem. Walkable to the ocean and natural pool and nice restaurant down the street. It is located in Sao Roque which is in the middle of the island so nothing is far away if you are driving. Parking ample...
The price is AED 749
AED 1,136 total
includes taxes & fees
1 Jun - 2 Jun
Adega do Mirante

Pico Formoso Vínea Lava Azores

9.8 out of 10, Exceptional, (6)
"Vinea lava was our favorite property we stayed in the Azores! A converted winery situated among Picos old stone-walled vines, photos do not do the view from the backyard justice. Kitchen was very new and updated. Bed was comfortable. Convenient, quiet location- a short walk from a lovely pool and wine bar with good food. Short 30 min drive to airport. Would love to stay there again!"
Pico Formoso Vínea Lava Azores

Cagarra Nest Winery

10.0 out of 10, Exceptional, (6)
"Beautiful view and sounds of the ocean waves. A short walk to the ocean."
Cagarra Nest Winery

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

The price is AED 957
AED 1,094 total
includes taxes & fees
2 May - 3 May
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

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

10.0 out of 10, Exceptional, (4)
"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."
The price is AED 998
AED 1,167 total
includes taxes & fees
2 May - 3 May
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
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.
Don't see what you're looking for?
See all available properties in Calheta
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Calheta

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

10.0 out of 10, Exceptional, (4)
"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."
The price is AED 998
AED 1,167 total
includes taxes & fees
2 May - 3 May
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

The price is AED 957
AED 1,094 total
includes taxes & fees
2 May - 3 May
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

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

The price is AED 732
AED 811 total
includes taxes & fees
2 May - 3 May
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
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.