Waterwine Travel - Vacation Rentals in Calheta

Quinta dos Encantos by AnaLodges From US $96
         

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9.8 (21 Reviews)
Apartment
  • Parking
  • Pool
  • Designated Smoking Area
Villa ElDoMar From US $895
         

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New
Villa
  • Pet Friendly
  • Pool
  • Designated Smoking Area

Luxury Places to Stay in Calheta

Over 2130+ Luxury Places to Stay in or Near Calheta
Cyane & Vigo's Cottage, Caminho do Massapez, n.º40 From US $3,155
         

10.0 (11 Reviews)
Ski Chalet
  • Parking
  • Balcony/Terrace
  • Child Friendly
Mea Suna From US $2,769
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pool
Villa Camacho - Ultra Luxury From US $1,930
         

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8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
Villa Sea Colors by An Island Apart From US $1,724
         

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10.0 (19 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Calheta

Over 946+ Top-Rated Vacation Rentals with a Pool in or Near Calheta
Casa Mar Azul From US $130
         

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10.0 (51 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Mango House From US $195
         

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10.0 (20 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Searenity Vacation Home II by An Island Apart From US $192
         

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10.0 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Vila Aguarelas with pool by Stay Madeira Island From US $109
         

Pet-Friendly Vacation Rentals in Calheta

Over 206+ Pet-Friendly Vacation Rentals in or Near Calheta
Homerez - Apartment in Prazeres From US $728
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Spectacular Cottage ECO-25 Fontes From US $122
         

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9.8 (5 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Mansion Almond From US $137
         

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10.0 (1 Review)
Villa
  • Parking
  • Pet Friendly
  • TV
Homerez - Apartment in Prazeres From US $609
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Homerez - Apartment in Prazeres From US $608
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Homerez - Apartment in Prazeres From US $596
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Typical Madeiran House - 23919 / AL From US $149
         

10.0 (41 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Santa Catarina House Madeira From US $129
         

10.0 (44 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Calheta on PetFriendly.io

Large Vacation Homes & Villas in Calheta

Over 558+ Large Vacation Homes & Villas in or Near Calheta
Stunning Villa w/Ocean Views & Heated Pool From US $494
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Villa da Silva - Heated Pool From US $113
         

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9.3 (7 Reviews)
Villa
  • Parking
  • Pool
  • Designated Smoking Area
Tranquil stone villa in Calheta | Casa Florenças From US $376
         

Villa Pinheira I, two bedrooms and sea view From US $213
         

9.8 (70 Reviews)
Villa
  • TV
  • Security/Safety
  • Bedding/Linens

Wheelchair Accessible Vacation Homes in Calheta

Over 77+ Wheelchair Accessible Vacation Homes in or Near Calheta
Villa Violetta From US $111
         

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8.4 (7 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Saccharum Resort From US $302
         

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9.4 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Calheta Hills I – With pool and sea view From US $916
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Calheta Hills III – Modern Retreat with Sea View From US $812
         

Calheta Hills II – Relax with Sea View and Pool From US $1,006
         

Calheta Hills IV – Apartment with Sea View From US $727
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Plaza Bay Luxury Apartment with Swimming Pool From US $139
         

8.6 (4 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible

Calheta Vacation Rentals and Airbnb Places to Stay Under $200

Over 1153+ Calheta Vacation Rentals and Airbnb Places to Stay Under $200
Maison Blanche with panoramic views of the sea, mountains and village From US $175
         

9.8 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Villa do Mar III From US $155
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Casa da Felicidade by LovelyStay From US $164
         

10.0 (3 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Recanto das Florenças (3) – Stone House From US $128
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Holiday house by the sea. From US $174
         

9.8 (11 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace

Instantly Bookable Vacation Homes in Calheta

Over 849+ Instantly Bookable Vacation Homes in or Near Calheta
Casa da Manta Fajã da Ovelha From US $463
         

Homerez - Studio - Ponta do Pargo From US $344
         

Angel's Sunset T1 From US $160
         

New
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities

About Calheta Vacation Rentals

With more than 2139 Calheta vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Waterwinetravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Calheta.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Waterwinetravel Calheta, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Calheta. Places to stay near Calheta are 1218.79 ft² on average, with prices averaging US $268 a night.

Waterwinetravel makes it easy and safe to find and compare vacation rentals in Calheta with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Calheta

Type Count
Vacation Homes 983
Holiday Apartments 524
Villas 482
Cottages 74
Ski Chalet Rentals 29
Others 15
Hotels 13
B&B 7
Cabin Rentals 5
Hostels 3
Resorts 3

Use these Quick Filters to Find a Vacation Rental in Calheta

Pro Tip: Waterwinetravel makes it easy to compare the best listings on Waterwinetravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Waterwinetravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Calheta.

Weather in Calheta

View the weather forecast for Calheta before booking your Calheta Vacation Rentals to confirm your best time to go.

December - February
High 73°F       Low 55°F
March - May
High 77°F       Low 59°F
June - August
High 83°F       Low 67°F
September - November
High 82°F       Low 64°F

Calheta Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Calheta?
How many vacation rentals are available in Calheta?

Currently, the total number of properties listed in 2026 is over 2139 in the Calheta area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Calheta.