Owner Direct Vacation Rentals in Calheta

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  3.  Portugal

  4.  Azores
  5.  Calheta

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25 Calheta Vacation Homes From $62

Looking for the ideal vacation rental in Calheta? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Vistalinda Farmhouse
Vistalinda Farmhouse
House
Fajã dos Vimes, Portugal
1.7k from Calheta center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms5 Guests
10.0

Exceptional

6 reviews

$128
Average price / night
Check Availability
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
House
São Jorge, 9850-209, Portugal
4.8k from Calheta center

AC, Crib, Fireplace, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$323
Average price / night
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Vistalinda Cabins
Vistalinda Cabins
Apartment
Calheta, Portugal
1.7k from Calheta center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom2 Guests
9.9

Exceptional

20 reviews

$92
Average price / night
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Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
House
São Jorge, 9850-209, Portugal
4.8k from Calheta center

AC, Crib, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$308
Average price / night
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Casas Dos Vimes
Casas Dos Vimes
House
Calheta, Azores, Portugal
1.9k from Calheta center

Cheap, Accommodations, Farm stays, Parking, Cottages, Lodgings, Vacation rentals, Places to stay, Self-catering

10 Bedrooms28 Guests
9.3

Superb

70 reviews

$77
Average price / night
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Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
House
São Jorge, 9850-209, Portugal
4.8k from Calheta center

AC, Balcony, Crib, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom3 Guests
New to Booking
$227
Average price / night
Check Availability
Casa Grão de Café AL
Casa Grão de Café AL
House
Fajã dos Vimes, Portugal
2.1k from Calheta center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

3 Bedrooms8 Guests
9.6

Exceptional

46 reviews

$62
Average price / night
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Beautiful 2 Bedroom Ocean Front Stone House In São Jorge,  Azores (Belo Canto)
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
House
São Jorge, 9850-209, Portugal
4.8k from Calheta center

AC, Internet, Kitchen, Living Area, No Smoking, Outdoor Space, Patio, Pool

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$313
Average price / night
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Casa da Eira
Casa da Eira
House
Portugal
2.2k from Calheta center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
8.6

Fabulous

29 reviews

$92
Average price / night
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Beautiful 2 Bedroom Ocean Front House In São Jorge,  Azores - Mamba
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba
House
São Jorge, 9850-209, Portugal
4.8k from Calheta center

AC, Internet, Kitchen, Living Area, No Smoking, Outdoor Space, Pool

2 Bedrooms5 Guests
New to Booking
$285
Average price / night
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Abrigo da Cascata - Casas de Campo - São Jorge
Abrigo da Cascata - Casas de Campo - São Jorge
House
Calheta, Portugal
2.5k from Calheta center

Accommodations, Farm stays, Parking, Cottages, Lodgings, Vacation rentals, Places to stay, Family

5 Bedrooms16 Guests
9.5

Superb

182 reviews

$139
Average price / night
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Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
House
Calheta, 9850-209, Portugal
5.1k from Calheta center

AC, Internet, Kitchen, No Smoking, Pool

1 Bedroom3 Guests
New to Booking
$249
Average price / night
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Caldeira Guesthouse
Caldeira Guesthouse
House
Calheta, Azores, Portugal
3.3k from Calheta center

B&bs, Cheap, Accommodations, Guest houses, Homestays, Pet-friendly, Lodgings, Vacation rentals, Beach

7 Bedrooms13 Guests
9.7

Exceptional

212 reviews

$98
Average price / night
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Casa de São João - Oceanfront 3BR/3BA Sunset View - Fajã de São João, São Jorge
Casa de São João - Oceanfront 3BR/3BA Sunset View - Fajã de São João, São Jorge
House
São Tomé, 9875027, Portugal
6.6k from Calheta center

Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$330
Average price / night
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Casa da Lagoa AL 416
Casa da Lagoa AL 416
House
Calheta, Azores, Portugal
3.6k from Calheta center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms6 Guests
9.2

Superb

16 reviews

$79
Average price / night
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Matilde's House, in the paradise Fajã de São João
Matilde's House, in the paradise Fajã de São João
House
Santo Antão, São Jorge, 9875-027, Portugal
7.0k from Calheta center

Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
9.0

Fabulous

6 reviews

$69
Average price / night
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Casa da Fajã - RRAL nº 635
Casa da Fajã - RRAL nº 635
House
Fajã da Caldeira de Santo Cristo, Portugal
3.7k from Calheta center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms6 Guests
9.0

Fabulous

14 reviews

$71
Average price / night
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Herdade das Hortênsias
Herdade das Hortênsias
House
São Jorge, 9875-029, Portugal
9.5k from Calheta center

Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$129
Average price / night
Check Availability
Kuanza Nature Experience, Fajã do Belo
Kuanza Nature Experience, Fajã do Belo
Apartment
Fajã da Caldeira de Santo Cristo, Portugal
4.8k from Calheta center

Apartments, Cheap, Accommodations, Pools, Lodgings, Vacation rentals, Beach, Places to stay, Family

16 Bedrooms42 Guests
9.7

Exceptional

157 reviews

$425
Average price / night
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Vista de Sonho
Vista de Sonho
Apartment
Calheta, Portugal
4.9k from Calheta center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms10 Guests
8.8

Fabulous

5 reviews

$87
Average price / night
Check Availability
Vista do Horizonte
Vista do Horizonte
Apartment
Calheta, Portugal
4.9k from Calheta center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom4 Guests
8.8

Fabulous

4 reviews

$71
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Calheta.

Where to stay in Calheta? Best neighborhoods & areas

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Calheta Vacation Rentals on the Map

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What makes our vacation rentals stand out?

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Verified Properties

Every vacation rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

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Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

There are a lot of options in Calheta. If you plan on staying in the Calheta area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Calheta

You can explore 25 verified vacation rentals in Calheta. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Calheta vary depending on the season, property size, and location. Rates typically start from around $62 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Calheta include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Calheta welcome pets. Currently, 5 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Calheta often include amenities such as View, Balcony/Terrace, and Child Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.