Calheta Holiday Rentals

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Our top choices for Calheta holiday rentals

Holiday Home in Calheta

Casas da Levada
9.8 out of 10, Exceptional, (17)
"Very nice place, clean and cosy little house. Well equipped, very friendly and helpful owner. Highly recommend."
United Kingdom
Grzegorz
Casas da Levada

Holiday Home in Calheta

Quinta das Vinhas
3.0 star property
9.2 out of 10, Wonderful, (59)
"Lovely location. Beautiful views and excellent food. I highly recommend it."
Canada
Ian
Quinta das Vinhas

Villa in Estreito da Calheta

Villa ElDoMar Heated Pool and Barbecue
10.0 out of 10, Exceptional, (3)
"Super"
Germany
Stefan S.
The price is NZ$713
includes taxes & fees
16 Jan - 17 Jan 2026
Villa ElDoMar Heated Pool and Barbecue

Cottage in Fajã da Ovelha

Ocean View Cottage, a Home in Madeira
8.0 out of 10, Very good, (1)
"Bon logement conforme à l’annonce avec une belle vue sur l’océan. Le propriétaire sérieux et agréable est facile à joindre. Bon séjour. "
France
Donovan D.
The price is NZ$537
includes taxes & fees
4 Jan - 5 Jan 2026
Ocean View Cottage, a Home in Madeira

Apartment in Calheta (Madeira)

Casa Ribeirinho by Madeira Real
The price is NZ$193
includes taxes & fees
13 Jan - 14 Jan 2026
Casa Ribeirinho by Madeira Real
10.0 out of 10, Exceptional, (2)
"Pros: Excellent location..."
United States
Anonymous traveller
The price is NZ$783
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Home 'Do Porto' with Sea View, Balcony and Wi-Fi

Apartment in Estrela da Calheta

Pool and sea view - Calheta Victory View
10.0 out of 10, Exceptional, (6)
"Super clean and modern apartment. Good and modern check-in and transparent communication. Would highly recommend and will book again inter future."
United States
Dennis E.
The price is NZ$622
includes taxes & fees
12 Jan - 13 Jan 2026
Pool and sea view - Calheta Victory View
10.0 out of 10, Exceptional, (31)
"Very nice place"
United States
Bernhard M.
The price is NZ$796
includes taxes & fees
30 Jan - 31 Jan 2026
Felicidade Rocha I, for families, with a pool.

Holiday Home in Arco Da Calheta

Villa Lilian - Three Bedroom House, Sleeps 6
10.0 out of 10, Exceptional, (1)
"Die Lage und der Sonnenuntergang mit Blick von der Terasse sind traumhaft. Der Villa fehlt es an nichts und die Ausstattung ist sehr stilvoll mit Liebe zum Detail. Es war alles wunderbar."
United States
Annika
The price is NZ$749
includes taxes & fees
21 Jan - 22 Jan 2026
Villa Lilian - Three Bedroom House, Sleeps 6

Apartment in Ilha da Madeira

Calheta Countryside - Studio with Terrace
8.0 out of 10, Very good, (1)
"Room clean, needed to play around with tv to get it working. Easy parking."
United States
Marco C.
The price is NZ$216
includes taxes & fees
2 Jan - 3 Jan 2026
Calheta Countryside - Studio with Terrace
8.8 out of 10, Excellent, (9)
"The house and Jacuzzi and BBQ were fantastic. I would recommend the owners install a dishwasher and provide a bbq grill tongs and bbq grill spatula as well as a better bbq grill grate over the fire."
United States
Jonathan W.
The price is NZ$842
includes taxes & fees
27 Jan - 28 Jan 2026
Swimming pool in Fajã da Ovelha - Casa da Maloeira

Apartment in Calheta

Discover Magical Calheta
The price is NZ$259
includes taxes & fees
5 Jan - 6 Jan 2026
Discover Magical Calheta

Apartment in Ilha da Madeira

Calheta Countryside - Studio with Balcony
The price is NZ$216
includes taxes & fees
2 Jan - 3 Jan 2026
Calheta Countryside - Studio with Balcony

Holiday Home in Arco da Calheta

With pool in Calheta - Villa Island Roots
10.0 out of 10, Exceptional, (2)
"Such a gem! This little house in the mountains is so cool. The pool, the view, the cinematic living room... it all combined for a wonderful family stay. The kids loved the pool and the parents loved the calmness of the surroundings. Totally recommended!"
Portugal
André L.
The price is NZ$704
includes taxes & fees
7 Jan - 8 Jan 2026
With pool in Calheta - Villa Island Roots
10.0 out of 10, Exceptional, (3)
"Pros: het zicht is fantastisch, het verblijf is mooi en proper Cons: -"
Netherlands
Anonymous traveller
The price is NZ$1,009
includes taxes & fees
18 Jan - 19 Jan 2026
Holiday Home 'Casa Homem Do Mar' with Sea View, Balcony and Wi-Fi
8.0 out of 10, Very good, (1)
"Pros: Ruime woonruimte met tuin gedeeltelijk in de zon waardoor niet al te warm. Altijd parkeergelegenheid voor de deur. Haven met restaurants waar je elke avond voor weinig en veel keuze heerlijk kunt eten. Cons: Slaapkamer is beneden aan de straat/parkeerterrein waar ook werklieden met vrachtauto's en trekkers langskomen; dit leverde veel geluid op. Voor verblijf met >2 personen onhandige verdeling met badkamer toilet alleen bereikbaar via slaapkamer beneden."
Netherlands
Anonymous traveller
The price is NZ$515
includes taxes & fees
9 Jan - 10 Jan 2026
Holiday Home 'Calheta Beach House T1' with Mountain View, Private Terrace and Wi-Fi
10.0 out of 10, Exceptional, (1)
"Wir waren insgesamt 10 Nächte in dieser wunderschönen Unterkunft. Wir fanden die Lage ideal zur Erkundung der Insel und haben den Aufenthalt sehr genossen. Ein besonderes Highlight ist die Aussicht vom Balkon und der Pool. Die Küche war auch sehr gut ausgestattet fürs Kochen. Wir würden immer wieder diese Unterkunft buchen!"
Germany
Greta S.
The price is NZ$719
includes taxes & fees
2 Jan - 3 Jan 2026
Calheta Hills II – Relax with Sea View and Pool
9.8 out of 10, Exceptional, (8)
"All in all a very good Place to be on holidays"
Germany
Robin S.
The price is NZ$376
includes taxes & fees
12 Jan - 13 Jan 2026
In the west - Intelsol Calheta Apartments II

Villa in Calheta

Casa Mozart II
4.0 star property
The price is NZ$697
includes taxes & fees
8 Jan - 9 Jan 2026
Casa Mozart II
10.0 out of 10, Exceptional, (4)
"Pros: La situation de la maison; l'équipement, complet et en parfait état; la gentillesse des hôtes."
France
Anonymous traveller
The price is NZ$1,058
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home 'Maravilha Da Costa' with Private Pool, Wi-Fi and Air Conditioning
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

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 favorite 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 depends 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 NZ$673 per night. Entering your travel dates in the search wizard you might find 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. Discover why Calheta is known for its spas and seaside. Allow some time to check out the marina during your trip.

What are some of the best holiday rentals that Calheta has to offer?

Casas da Levada: This highly rated holiday home rental in Calheta is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. It offers a furnished patio, a terrace and a private garden so that you can immerse yourself in your holiday. Other favourite homes for rent in Calheta are Home for Nature Tourism, Madeira Island LAURISHOUSE, Nature and Sea and Home for Nature Tourism, Madeira Island LEAHOUSE, Nature and Sea.

How many holiday rentals are there in Calheta?

With 343 Expedia holiday rentals, you're guaranteed to find just the right place for your Calheta stay.

What’s there to see and do in Calheta?

Paul do Mar Beach and 25 Fontes and Cascada da Risco are a couple of scenic spots to enjoy the outdoors, whereas Casa das Mudas Arts Center is one of the cultural attractions. Other places in town to visit include Eglise de Faja da Ovelha and Levada Pedregal.

What’s a holiday rental in Calheta like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Calheta. Holiday rentals feature amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for families.