Calheta Vacation Rentals from CA $243: Short-Term Rentals for 2026

Q: What are some of the best vacation rentals in Calheta?

Casas da Levada : Visitors give good reviews to this Calheta vacation home rental, which is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. It offers a furnished patio, a terrace, and a private yard so you can immerse yourself in your vacation. Other favorite homes for rent in Calheta are Casa Félix, Calheta: Villa with unique view! Private Pool! and Villa Tomito, Arco da Calheta .

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Our top choices for Calheta vacation rentals

A clear blue pool with a view of the ocean.

1. Casas da Levada

Calheta

Jin-Ah

CA $274 total

includes taxes & fees

Nov 18 - Nov 19

A modern living room with a white sofa, a glass coffee table, and a colorful rug. A kitchen with white cabinets and a large window is visible in the background.

2. Villa ElDoMar Heated Pool and Barbecue

Estreito da Calheta

Stefan S.

CA $554 total

includes taxes & fees

Nov 25 - Nov 26

A bedroom with a bed, pillows, a bedside table, a mirror, and a view of a kitchen and bathroom through a sliding door.

3. Apartment "Calheta Lofts I" with Mountain View, Private Balcony & Wi-Fi

Lombo Do Doutor

CA $183 total

includes taxes & fees

Nov 18 - Nov 19

4. Apartment "Calheta Lofts II" with Mountain View, Private Balcony & Wi-Fi

Lombo Do Doutor

CA $183 total

includes taxes & fees

Nov 16 - Nov 17

A swimming pool with lounge chairs, a lifebuoy, and a stone wall.

5. Vila Maria Quinta 6 "Os Borracheiros "

Calheta

anneke v.

CA $181 total

includes taxes & fees

Nov 30 - Dec 1

A sandy beach with a rocky shoreline and a mountain in the background.

6. Private room with en-suite and private access

Estrela da Calheta

CA $73 total

includes taxes & fees

Nov 25 - Nov 26

A balcony with a view of the sea, a railing, and a building entrance.

7. GuestReady - Casa das Estrelas

Estreito da Calheta

CA $353 total

includes taxes & fees

Nov 29 - Nov 30

An infinity pool with clear blue water and a view of the ocean.

8. Calheta Hills V – Sea View and Pool in Calheta

Estrela da Calheta

CA $449 total

includes taxes & fees

Nov 21 - Nov 22

9. Calheta Hills III – Modern Retreat with Sea View

Estrela da Calheta

Christopher U.

CA $497 total

includes taxes & fees

Nov 26 - Nov 27

10. Calheta Hills I – With pool and sea view

Calheta

erin p.

CA $948 total

includes taxes & fees

Dec 9 - Dec 10

A modern living room with a flat-screen TV, a white console table, a grey sofa, and a large plant.

11. West of the island - Intelsol Calheta Apartments I

Calheta

Sharon W.

CA $498 total

includes taxes & fees

Dec 2 - Dec 3

12. Calheta Hills IV – Apartment with Sea View

Estrela da Calheta

Giada P.

CA $483 total

includes taxes & fees

Nov 30 - Dec 1

A room with two windows, a painting, a lamp, and a table with a plant.

13. Holiday Home 'Calheta Beach House T1' with Mountain View, Private Terrace and Wi-Fi

Lombo Do Doutor

"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."

Anonymous traveller

CA $367 total

includes taxes & fees

Nov 13 - Nov 14

A modern living room with a sofa, TV, and coffee table. A kitchen is visible in the background.

14. Relax Garden House – Tranquility & Comfort

Arco da Calheta

Michel B.

CA $408 total

includes taxes & fees

Nov 12 - Nov 13

A patio with outdoor furniture, a dining table, and a potted plant.

15. Apartment 'Casinha Gomes' with Sea View

Calheta

CA $242 total

includes taxes & fees

Dec 2 - Dec 3

A residential area with houses, a winding road, and a construction crane.

16. Palmasol II – Peaceful, Spacious 3-Bed in Calheta

Estrela da Calheta

CA $622 total

includes taxes & fees

Dec 1 - Dec 2

A balcony with a potted plant, overlooking a coastal landscape with houses and greenery.

17. Calheta Countryside - Studio with Balcony

Ilha da Madeira

CA $157 total

includes taxes & fees

Nov 11 - Nov 12

A balcony with outdoor furniture, a table with a cup and saucer, and a view of the sea.

18. Apartment 'Casa Gomes' with Sea View, Wi-Fi and Air Conditioning

Calheta

CA $246 total

includes taxes & fees

Dec 9 - Dec 10

A pool area with lounge chairs, palm trees, and a view of the ocean at sunset.

19. Suite Bela Vigia 4 Room with Sea View, Wi-Fi, and Air Conditioning

Jardim do Mar

CA $282 total

includes taxes & fees

Nov 12 - Nov 13

A yellow building with a red-tiled roof and a small balcony.

20. Calheta Countryside - Studio with Terrace

Ilha da Madeira

Marco C.

CA $157 total

includes taxes & fees

Nov 15 - Nov 16

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Top Calheta Hotel Reviews

SPECIAL OFFER VISIT Madeira FebruaryWarm Pool Gardens terraces comfort

10/10 Excellent

"Absolutely incredible villa to stay in for a family of 4, with a hire car who did lots of hiking! The space was lovely, kids loved the heated pool, and everything was provided! And so many towels!!! Which was sooo useful Thank you Sandra for always communicating with us! We will be back!"

Villa Tomito, Arco da Calheta

10/10 Excellent

"We stayed at Villa Tomito for our honeymoon and absolutely loved it. Thomas and Jhonny went above and beyond in preparing an amazing surprise for us!! The apartment itself is brilliant - we have never seen such a well equipped kitchen, and it is very spacious and clean. The balcony has beautiful views down to the coast and is very well located for the PR6 Levada trails and Fanal Forest in particular. We would highly recommend."

Calheta Beach - All Inclusive

8/10 Good

"The food was very interesting. Some overcooked. There were ants in the dessert. We often resorted to the restaurants along the pier. They also forgot to put my birthday amenity until after we arrived but all in all the hotel was beautiful and had a very scenic view to gaze upon the mountains, oceans and sunsets. I wish it was closer to Funchal as it’s 40 minutes away and quite expensive to frequently travel to. The area is quite limited with activities so having a shorter stay would’ve been a better idea to see more of the island. But nice if you’re looking to just relax."

Spacious villa, 180* ocean view, large heated pool, 5 min from Calheta beach

10/10 Excellent

"Wonderful home with plentiful amenities. Great location on island and communication with owner was superb. Only complaint was that we paid extra for a heated pool and didn’t get to use it, bummer!"

Casa Félix, Calheta: Villa with unique view! Private Pool!

10/10 Excellent

"Casa Felix is an outstanding property. Alferdo, and Celia have impeccable taste the home has all you will need for your stay in Madeira. The welcome basket is a very nice touch. One you stay at Casa Felix you will see why they are premier hosts. Thank you for a fantastic stay,Paul & Elizabeth"

Beautiful large property with private heated pool

10/10 Excellent

"The property was comfortable and peaceful with sea views, and well-located for levada walks. We mostly stayed in of an evening, rather than eating out, to enjoy the ambience. Access was steep, so if hiring a car, we would recommend taking account of that. The pool was a little cooler than we are used to, but was fine in the daytime early October sunshine. We would book it again."

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Calheta vacation rentals we have selected for you start as low as CA $243 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 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.

Frequently asked questions

Are there vacation rentals in Calheta?

Yes, you can find vacation rentals in Calheta close to Casa das Mudas Arts Center, or you can choose a secluded option if you'd like a relaxing place to 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 vacation rentals in Calheta?

Casas da Levada: Visitors give good reviews to this Calheta vacation home rental, which is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. It offers a furnished patio, a terrace, and a private yard so you can immerse yourself in your vacation. Other favorite homes for rent in Calheta are Casa Félix, Calheta: Villa with unique view! Private Pool! and Villa Tomito, Arco da Calheta.

How many vacation rentals are there in Calheta?

With 320 Expedia vacation rentals, you're sure to find just the right place for your Calheta stay.

What’s there to see and do in Calheta?

25 Fontes and Cascada da Risco and Paul do Mar Beach 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 Calheta Beach.

What’s a vacation rental in Calheta like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Calheta. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for families.

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Check prices for these dates

Our top choices for Calheta vacation rentals

1. Casas da Levada

2. Villa ElDoMar Heated Pool and Barbecue

3. Apartment "Calheta Lofts I" with Mountain View, Private Balcony & Wi-Fi

4. Apartment "Calheta Lofts II" with Mountain View, Private Balcony & Wi-Fi

5. Vila Maria Quinta 6 "Os Borracheiros "

6. Private room with en-suite and private access

7. GuestReady - Casa das Estrelas

8. Calheta Hills V – Sea View and Pool in Calheta

9. Calheta Hills III – Modern Retreat with Sea View

10. Calheta Hills I – With pool and sea view

11. West of the island - Intelsol Calheta Apartments I

12. Calheta Hills IV – Apartment with Sea View

13. Holiday Home 'Calheta Beach House T1' with Mountain View, Private Terrace and Wi-Fi

14. Relax Garden House – Tranquility & Comfort

15. Apartment 'Casinha Gomes' with Sea View

16. Palmasol II – Peaceful, Spacious 3-Bed in Calheta

17. Calheta Countryside - Studio with Balcony

18. Apartment 'Casa Gomes' with Sea View, Wi-Fi and Air Conditioning

19. Suite Bela Vigia 4 Room with Sea View, Wi-Fi, and Air Conditioning

20. Calheta Countryside - Studio with Terrace

Find vacation rentals that suit your style

Top Calheta Hotel Reviews

SPECIAL OFFER VISIT Madeira FebruaryWarm Pool Gardens terraces comfort

Villa Tomito, Arco da Calheta

Quinta das Vinhas

Saccharum Resort

Calheta Beach - All Inclusive

Spacious villa, 180* ocean view, large heated pool, 5 min from Calheta beach

Casa Félix, Calheta: Villa with unique view! Private Pool!

Hotel Jardim Atlantico

Beautiful large property with private heated pool

Find out more about Calheta

Frequently asked questions

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