Calheta Vacation Rentals from CA $284: Short-Term Rentals for 2025

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 an espresso 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 Villa Tomito, Arco da Calheta and Casa Félix, Calheta: Villa with unique view! Private Pool! .

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Vacation Rentals in Calheta

Enjoy a serene retreat in this house surrounded by lush greenery and a pool.

"Really lovely hotel and room, very quiet and peaceful setting within the vines. "

CA $308 total

includes taxes & fees

Jul 19 - Jul 20

Relax by the serene pool surrounded by a natural landscape and ocean views.

"Very nice place, clean and cosy little house. Well equipped, very friendly and helpful owner. Highly recommend."

CA $422 total

includes taxes & fees

Jul 24 - Jul 25

CA $289 total

includes taxes & fees

Jul 26 - Jul 27

Relax in this charming room with a plush bed, wooden headboard, and cozy bench.

CA $361 total

includes taxes & fees

Jul 28 - Jul 29

"Pros: Sehr hell, großzügige Räume. Alles sauber und freundlich eingerichtet. Dankeschön"

CA $614 total

includes taxes & fees

Jul 19 - Jul 20

"Pros: het zicht is fantastisch, het verblijf is mooi en proper Cons: -"

CA $1,247 total

includes taxes & fees

Jul 31 - Aug 1

Relax by the pool with a view of the surrounding hillside, surrounded by lounge chairs and towels.

"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!"

CA $3,707 total

includes taxes & fees

Aug 10 - Aug 11

CA $3,372 total

includes taxes & fees

Aug 2 - Aug 3

Relax by the serene pool surrounded by lush greenery and a clear sky.

"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."

Relax in this serene space with a wooden dining table, wicker chairs, and a stunning stained glass chandelier.

"Great Place To Stay. Good value for money. Very clean. Quiet neighbourhood (except barking dogs). You definitely need a car to get around. Staff was helpful and friendly. Would come here again anytime again!"

CA $1,210 total

includes taxes & fees

Jul 27 - Jul 28

CA $1,917 total

includes taxes & fees

Aug 8 - Aug 9

"Pros: Excellent location..."

CA $863 total

includes taxes & fees

Jul 23 - Jul 24

CA $7,363 total

includes taxes & fees

Jul 23 - Jul 24

Enjoy a refreshing swim with a breathtaking view of the surrounding landscape from our rooftop pool.

"The house is beautifully located and the views from the terrace are stunning. It is a small but very lovely stone house with all the necessary comfort and with a lot of charme. The very steep road to get there and the narrow entrance to the parking space required some getting used to, but after a few days this was not worth a thought anymore (but we were happy to have a mini SUV...). We were very pleased and would come back again anytime."

CA $1,677 total

includes taxes & fees

Jul 22 - Jul 23

Enjoy a serene swim with ocean views and a hillside backdrop.

"Stay for 5 days and was amazing I recommend 😍"

CA $3,254 total

includes taxes & fees

Aug 4 - Aug 5

"Stayed in this beautiful modern home with my friend. We had some trouble locating this unit as it is slightly hidden from the main road and the address does not bring you to the door front. We were greeted by the owner just 5-10min after our scheduled check-in time. It was more than enough space for the two of us, so it will definitely accommodate a small family of four, a family of 3 adults/2 children, or a group of 3-5 friends comfortably. The two washrooms on both levels were convenient...

CA $861 total

includes taxes & fees

Jul 19 - Jul 20

Enjoy a meal under the shade of a large tree in this serene outdoor dining area.

"altes Häuschen, einfach gehalten, die Ausstattung ist auch eher einfach, zu wenig zweckmäßige Küchengerätschaften, in den Schränken riecht es sehr stark nach Schimmel, die Lage ist sehr schön und abgelegen, allerdings könnte man den Garten etwas mehr pflegen und es fehlen unbedingt Sonnenliegen, die wir zwar nachgefragt haben aber nicht erhielten, schade..."

CA $1,410 total

includes taxes & fees

Aug 3 - Aug 4

Relax by the serene pool, surrounded by lush flowers and a beautiful statue.

"Ein Ort zum entspannen , ein Ort für absolute Ruhe, für Spaziergänge, Wanderungen jeglicher Art - Ponta do Pargo , 4 Minuten Autofahrt , tolles Kaffee mit tollem Frühstück ( gato legal ) - Pendravista eine portugiesische Bar mit ehrlichem portugiesischem Essen und toller Musik aus den 80‘iger Jahre !"

CA $2,519 total

includes taxes & fees

Jul 30 - Jul 31

CA $727 total

includes taxes & fees

Jul 27 - Jul 28

"Pros: Geschmackvoller Wohnbereich, gute Ausstattung Cons: Schlafzimmer zur Straße sehr laut"

CA $1,323 total

includes taxes & fees

Jul 25 - Jul 26

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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 $284 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.

Recent reviews of Calheta properties

5/5 Excellent

"We arrived late in the evening after our transfer from the airport. The resort had arranged the transfer for us and the driver was waiting at arrivals for the 8 of us in our group. He was great and gave us a bit of a tour on the way to Calheta. Our reception at the resort went well and the woman on duty made sure we got down to the buffet before it closed. She was very friendly and attentive to our needs after a long day of travel. Our rooms were modern and clean and cleaned and tidied well each day by the cleaning staff, The buffet was great with a large selection of food items. Drinks at the bar were served quickly and were good. The "drink of the day" by the pool was excellent on the 2 days we had them. The resort is in a beautiful location, nestled below a cliff. There is a public beach next to the resort which has great sand and water access. Evening entertainment was fairly low key but pleasant as we enjoyed the evening by the pool while listening to a musician or watching the dancers. We had no complaints about the staff at the resort. They were friendly and did their job well. All in all I would recommend staying at this all inclusive Calheta Beach Hotel on the beautiful island of Madeira."

A verified traveller stayed at Calheta Beach - All Inclusive

Posted 5 days ago

Home for Nature Tourism, Madeira Island LEAHOUSE, Nature and Sea

5/5 Excellent

First connection with the island

"Três bien située pour nos vacances,la tranquillité de l endroit nous a permis de faire ce que nous avions de prévu. Les commodités étaient proches et atteindre les points de visite sur l île se faisait sans encombres. "

A verified traveller stayed at Home for Nature Tourism, Madeira Island LEAHOUSE, Nature and Sea

Posted 8 days ago

Take full advantage of a relaxing atmosphere with gorgeous sea/ mountain views

5/5 Excellent

Stunning little property

"Location was superb for exploring the island as well as evening walks. The local cafe's were great for snacks and poncha! We made use of the pool and garden room most days. Views from the villa were lovely and it was very quiet and peaceful. Alberto was a fantastic host - very responsive. Would definitely recommend. "

A verified traveller stayed at Take full advantage of a relaxing atmosphere with gorgeous sea/ mountain views

Posted 2 weeks ago

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

5/5 Excellent

Great communication

"Beautiful houseVery comfortable Great owners and the property manager! "

A verified traveller from Canada stayed at Spacious villa, 180* ocean view, large heated pool, 5 min from Calheta beach

Posted 3 weeks ago

Luxury villa by the sea with private pool, terrace and sea view

5/5 Excellent

"My husband and I stayed at this lovely villa to celebrate our anniversary. The villa is a gem of a home. The views out over the sea are splendid. We spent a lot of time outdoors on the terrace and cooking in the brilliant outdoor kitchen (which we loved). We also swam in the pool every day and the loungers are a great place to relax. The gardens are wonderful with mature trees and shrubs. The setting is very peaceful and we loved coming back to the serenity of the villa. We spent more time there than we thought that we would just because it is so nice. The villa itself is spacious, clean and well equipped with great views from every room. The beds are very comfortable and the en-suite showers are powerful and hot. Emanuel is a very kind and helpful host. We arrived very late in the night and Emanuel had left us some lovely gifts for our anniversary. We met him later in the week and he is very friendly and a lovely man. Communication was great. He couldn't have done more to make us feel welcome.Would definitely recommend this villa and we would love to stay again on another visit to Madeira. "

A verified traveller stayed at Luxury villa by the sea with private pool, terrace and sea view

Posted 1 month ago

Quinta Pereira ... beautiful panoramic views and ocean sunsets

5/5 Excellent

The Sunsets Linger On...

"We spent 6 nights in Funchal and 3 nights at Quinta Pereira. QP was a wonderful counter-balance to a busy first week. Contemporary and tastefully appointed villa, gorgeous patios and terraces, lovely pool and hot tub, and stunning views. Amenities, restaurants et al are a 10-15 minute drive away. A surreal retreat for two couples."

A verified traveller stayed at Quinta Pereira ... beautiful panoramic views and ocean sunsets

Posted 2 months ago

Frequently asked questions

Are there vacation rentals in Calheta?

Yes, you can find vacation rentals close to popular local attractions in Calheta, or you can choose a more remote option if you want 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 an espresso 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 Villa Tomito, Arco da Calheta and Casa Félix, Calheta: Villa with unique view! Private Pool!.

How many vacation rentals are there in Calheta?

With 395 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?

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 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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Calheta Vacation Rentals

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Vacation Rentals in Calheta

Quinta das Vinhas

Quinta das Vinhas

Casas da Levada

Casas da Levada

Room 'Suite Bela Vigia 3' with Shared Pool, Shared Garden and Wi-Fi

Room 'Suite Bela Vigia 3' with Shared Pool, Shared Garden and Wi-Fi

Palheiro Mar by Olá Madeira

Palheiro Mar by Olá Madeira

Holiday Home 'Mother's House' with Sea View, Private Terrace and Wi-Fi

Holiday Home 'Mother's House' with Sea View, Private Terrace and Wi-Fi

Holiday Home 'Casa Homem Do Mar' with Sea View, Balcony and Wi-Fi

Holiday Home 'Casa Homem Do Mar' with Sea View, Balcony and Wi-Fi

With pool in Calheta - Villa Island Roots

With pool in Calheta - Villa Island Roots

Holiday Home "Villa Camacho iv - Mansion House" with Sea View, Pool & Wi-Fi

Holiday Home "Villa Camacho iv - Mansion House" with Sea View, Pool & Wi-Fi

Pool and comfort in Fajã da Ovelha - Casa da Maloeira

Pool and comfort in Fajã da Ovelha - Casa da Maloeira

Country House in Fajã da Ovelha - Casa da Raposeira

Country House in Fajã da Ovelha - Casa da Raposeira

Holiday Home 'Maravilha Da Costa' with Private Pool, Wi-Fi and Air Conditioning

Holiday Home 'Maravilha Da Costa' with Private Pool, Wi-Fi and Air Conditioning

Holiday Home 'Do Porto' with Sea View, Balcony and Wi-Fi

Holiday Home 'Do Porto' with Sea View, Balcony and Wi-Fi

Holiday Home "Villa Camacho - Ultra Luxury" with Sea View, Pool & Wi-Fi

Holiday Home "Villa Camacho - Ultra Luxury" with Sea View, Pool & Wi-Fi

Refúgio da Serra - By Wehost

Refúgio da Serra - By Wehost

House with pool and sea view, Pearl of Calheta

House with pool and sea view, Pearl of Calheta

Holiday Home 'Melblue' with Sea View, Private Terrace and Wi-Fi

Holiday Home 'Melblue' with Sea View, Private Terrace and Wi-Fi

Um Refúgio Para Férias em Família, Quinta da Fonte

Um Refúgio Para Férias em Família, Quinta da Fonte

With pool and barbecue - Villa Roque

With pool and barbecue - Villa Roque

Country House 'Serrão' with Private Terrace, Private Garden and Wi-Fi

Country House 'Serrão' with Private Terrace, Private Garden and Wi-Fi

Holiday Home 'Calheta Beach House T2' with Mountain View, Private Terrace and Wi-Fi

Holiday Home 'Calheta Beach House T2' with Mountain View, Private Terrace and Wi-Fi

Find out more about Calheta

Find out more about Calheta

Recent reviews of Calheta properties

Recent reviews of Calheta properties

Calheta Beach - All Inclusive

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Explore a world of travel with Expedia

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