Calheta Vacation Rentals from CA $420: 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 .

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Calheta vacation rentals

A cobblestone path leading to a stone building with a red door, surrounded by lush hydrangea bushes.

1. Quinta das Vinhas

Calheta

Simon

CA $290 total

includes taxes & fees

Oct 26 - Oct 27

A rustic stone building with a wooden door marked "B2" and a wooden window with a cross-shaped shutter.

2. Palheiro Jardim by Olá Madeira

Paúl do Mar

Dominic G.

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.

3. Villa ElDoMar Heated Pool and Barbecue

Estreito da Calheta

Stefan S.

CA $625 total

includes taxes & fees

Oct 4 - Oct 5

A clear blue pool with a view of the ocean.

4. Casas da Levada

Calheta

Jin-Ah

CA $420 total

includes taxes & fees

Oct 2 - Oct 3

A stone building with a tiled roof overlooking the sea.

5. Palheiro Mar by Olá Madeira

Paúl do Mar

CA $302 total

includes taxes & fees

Oct 4 - Oct 5

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

6. Calheta Countryside - Studio with Terrace

Ilha da Madeira

Marco C.

CA $179 total

includes taxes & fees

Oct 13 - Oct 14

7. Home Thomas - Calheta o Conforto na Natureza

Lombada dos Marinheiros

Pierre A.

CA $212 total

includes taxes & fees

Sep 29 - Sep 30

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

8. Calheta Countryside - Studio with Balcony

Ilha da Madeira

CA $172 total

includes taxes & fees

Oct 11 - Oct 12

View all properties

Find vacation rentals that suit your style

Villas

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Calheta Hotel Reviews

Saccharum Resort

10/10 Excellent

"The Evening buffet didn’t meet our expectations. It had overdone meat in several different options. The food wasn’t hot and the salads were almost gone. We both didn’t think it was worth the money. The breakfast buffet was much higher standard. Couldn’t fault anything else. Design, staff, cleanliness and facilities were exceptional"

Calheta Beach - All Inclusive

8/10 Good

"Lovely hotel, with great sea view rooms. We had premium All inclusive which was well worth it for the al carte breakfast and additional nights at the restaurants. Swimming pools are great, mostly couples there, a few young children as not a child friendly hotel really. It's 4 euros to play pool for an hour, which is fair. One critisim is the number of flies and bugs. At the buffet/drink stations there are a lot of flies, with cakes/lemons/honey left out. It was a bit off putting, however it was always cleaned if something left out / causing the issue. We did get a lot of bites at night as well, including inside and mostly around ankles and feet - take bug spray. The shuffle service to Funchal isn't worth it, better to get an uber if a couple, can come and go as you please and the same money, choose CR7 as the drop off point. Lots of vegetarian options in the buffet also and proper drinks brands served. Entertainment was okay, mostly live music."

SPECIAL OFFER VISIT Madeira FebruaryWarm Pool Gardens terraces comfort

10/10 Excellent

"This villa was everything and more than we could have wished for. Sandra met us on arrival to show us round and continued to communicate well throughout our stay. The villa it self was extremely clean and the facilities there is everything you need for the perfect stay. The highlight for us was the outdoor kitchen bbq area where we spend most of our time in the evenings and when we weren’t out seeing the sights. The pool was perfect for cooling off in the hot afternoons. The views are absolutely perfect and the area is very quiet. The marina is only a short drive away which is nice for evening strolls and has some wonderful restaurants to dine in. We found it to be the perfect location for our holiday in Madeira. We would highly recommend a stay here and would definitely want to stay here again in the future."

Quinta Pereira ... beautiful panoramic views and ocean sunsets

10/10 Excellent

"We had an amazing stay at Quinta Pereira, which is beautifully positioned in a peaceful spot commanding amazing views of the coastline. The property has multiple areas to sit in the gardens and enjoy the views and offers lots of different ways to keep guests entertained, from pool and table football through to the piano (a very welcome surprise), board games and even an XBOX (latest model, which our 17yo managed to leave alone for once, thrashing us at table football instead!). A hire car is essential as the area's very hilly and we'd recommend a small car or an SUV - our saloon estate was too long and low to clear the bump at the gate and park on the drive - but Wendy was only too happy for us to use the parking space by the road.Walking the levadas and a trip to the lava pools of Porto Moniz were real highlights, as were the Sunshine Pub & Grill and Restaurante O Forno.Wendy was a really responsive host and we'd have no hesitation in returning to this tranquil spot, or recommending to others."

ANGEL'S SUNSET T2 ESTRITO DA CALHETA

10/10 Excellent

"Had mostly everything that we needed. Clean and comfortable and with good facilities including designated parking.The only things I would like to see added:1. A kettle - us Brits like a cup of tea and some of us even like instant coffee.2. Fans for the bedrooms. As they don't have windows it can get stuffy and hot overnight.Our host, Elisabete, was wonderful. Gave us some welcome gifts and advice on where to go and what to do.Be aware that this is a set of 4 apartments that share the outdoor facilities. I didn't cotton onto that when I booked."

House / Villa - Arco da Calheta

8/10 Good

"Sehr gute Unterkunft und vor allem die perfekte Lage ( 5 Minuten und du bist am Strand). Das Haus wie beschrieben, sauber, mit allem notwendigen ausgestattet. Sehr große Terrase mit dem Blick auf die Atlantik. Die Kommunikation lief reibungslos, die Betreuung vor Ort ebenfalls. Viele Dank dafür. Was das Parken angeht, ist generell auf Madeira eine Herausforderung, da die Straßen sehr eng und steil sind, aber machbar. Ein Tipp für den Strand. Wir haben uns für den Strand, wo meistens die Einheimische sind, entschieden. Im Navi einfach Ficus Julia im Madalena do Mar angeben. Der ist zwar steinig, aber mit einem kristall sauberem Wasser und nicht überfüllt wie in Calheta (außer am WE), mit einem großen kostenlosen Parkplatz. Da kann man sich nach dem Schwimmer einen Hotdog oder Hamburger (wirklich zu empfehlen, ist groß, lecker und macht einen richtig satt) holen. Fazit: Preis -Leistungs Verhätnis stimmt. Ich würde die Unterkunft auf jeden Fall weiter empfehlen."

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

10/10 Excellent

"We had an amazing stay at Casa Felix. The property is exactly as shown on the listing and is stunning. It was immaculately clean and very comfortable and well equipped. The master bedroom bed was very comfortable, although quite hard, and there were plentiful towels and good quality bed linen. The outside space is the real wow-factor and allows you to enjoy the spectacular view, which we never tired of looking at. Our check-in process was very smooth, and Celia met us at the property to complete a full hand over. She was very helpful and gave us recommendations for local services we may need. The villa is located at the top of a very steep hill. It is about a 15 minute walk down the hill to the port, but we didn’t attempt the walk back up. On a couple of occasions we got a taxi, but these were hard to find after about 9pm, even at the weekend, and there was no Uber service available. Therefore, most of the time we drove. I would recommend getting the smallest hire-car possible as the road is narrow, precipitous and incredibly twisty, best suited to very experienced drivers. Casa Felix is a stunning property that exceeded our expectations, and we very much enjoyed our time staying there."

Villa ElDoMar Heated Pool and Barbecue

10/10 Excellent

"Beautiful house and really good in communication during our stay. The view vom all rooms is breathtaking und the pool was perfect to jump in after a day out! The kitchen has almost all you need! Just a a little add on. The communication before our stay was a little challenge, which definitely should be improved. I did not receive any answers for weeks on my message during FeWo even contacting FeWe support didn’t help. The answer came serval days later."

Find out more about Calheta

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Calheta. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 318 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Calheta vacation rentals

1. Quinta das Vinhas

2. Palheiro Jardim by Olá Madeira

3. Villa ElDoMar Heated Pool and Barbecue

4. Casas da Levada

5. Palheiro Mar by Olá Madeira

6. Calheta Countryside - Studio with Terrace

7. Home Thomas - Calheta o Conforto na Natureza

8. Calheta Countryside - Studio with Balcony

9. Erdhaus by Interhome

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

11. In the west - Intelsol Calheta Apartments II

12. Casa Maria Bela – 2-Bedroom with Terrace

13. Apartment 'Referta Apartamento T1' with Sea View, Private Terrace and Wi-Fi

14. Casa Fábrica da Manteiga - Historic house

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

16. Room 'Suite Vigia Jardim' with Sea View, Wi-Fi and Air Conditioning

17. Casa Belo Jardim - Studio with garden

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

19. Soulglamping – Rückzugsort – Natur – Meerblick – Sonne

20. Antiga Fábrica da Manteiga – Traditional House

Find vacation rentals that suit your style

Top Calheta Hotel Reviews

Saccharum Resort

Calheta Beach - All Inclusive

SPECIAL OFFER VISIT Madeira FebruaryWarm Pool Gardens terraces comfort

Quinta Pereira ... beautiful panoramic views and ocean sunsets

ANGEL'S SUNSET T2 ESTRITO DA CALHETA

House / Villa - Arco da Calheta

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

Villa Tomito, Arco da Calheta

Villa ElDoMar Heated Pool and Barbecue

Find out more about Calheta

Frequently asked questions

Go further with the Expedia app