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Villa holiday rentals in Calheta

Find and book unique villas on Airbnb

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Popular amenities for villa rentals in Calheta

Private villa rentals

Superhost
Villa in Calheta
4.86 out of 5 average rating, 90 reviews

Villa Fedra - A hidden paradise

HenningRating, 5 stars7 months ago
Lovely garden and my daughter loved picking oranges herself and squeezing them to juice for breakfast.
Guest favourite
Villa in Arco da Calheta
4.88 out of 5 average rating, 16 reviews

Paradise views - Pereira House

DylanRating, 5 stars1 week ago
Nous venons tout juste de rentrer d’une semaine de vacances dans le logement de Luis. Maison impeccable, rien à dire sur la propreté ! Tout correspondait à la description de l’annonce ! Seules petites améliorations : le manque de rangement pour poser les affaires dans les chambres et la salle de bain, et un étendoir un peu petit au vu de la capacité de la maison ! Autrement, notre séjour était parfait, la maison et sa vue étaient top ! Nous vous recommandons grandement ce logement !
Guest favourite
Villa in Arco da Calheta
5 out of 5 average rating, 19 reviews

Ohana Ocean View by LovelyStay

JulietteRating, 5 stars1 week ago
We absolutely loved our stay in Madeira! The property was incredibly clean—honestly one of the cleanest places we've ever stayed. Everything was spotless and so well maintained. The welcome gifts were such a thoughtful touch—local produce that gave us a warm introduction to the island. The house had everything we needed, from great coffee to handy extras like Tupperware, which made day trips really convenient. The sunsets from the property were absolutely stunning—something we looked forward to every evening. The location was great for accessing shops and restaurants nearby, but we’d definitely recommend having a car to explore more of the island comfortably. All in all, a fantastic stay. We’d return in a heartbeat!
Guest favourite
Villa in Machico
4.9 out of 5 average rating, 60 reviews

Casa Privada com 2 suítes - Urban Farm 1

MaryRating, 5 stars2 weeks ago
Luna hat uns geholfen, dass wir mitten in der Nacht anreisen konnten, das war fantastisch! Wir haben sogar einen kleinen Snack bekommen, dass wir nicht hungrig schlafen gehen müssen. Die Küche und Terrasse sind ganz liebevoll eingerichtet, sodass man sich richtig wohlfühlt. Wir hatten nette Nachbarn, die wir beim Frühstück getroffen haben. Abends konnten wir problemlos in die Stadt laufen. Wir sind froh, dass wir in dieser gemütlichen Unterkunft unseren Madeira Urlaub beginnen konnten.
Superhost
Villa in Paul do Mar
4.8 out of 5 average rating, 45 reviews

New! OCEAN PARADISE Beach Villa 100M from beach

JulieRating, 5 stars1 month ago
Grande maison idéale pour une famille, belle cuisine, terrasse et vue sur la mer. Iva est une hote acceuillante qui prends le temps de nous laisser de nombreuses informations pour découvrir cette belle île. Ainsi nous avons pu aller découvrir les dauphins à prix préférentiel et zn passant par une agence locale 😊... Le logement est situé dans le sud ouest de l'île, dans un petit village de pêcheurs au calme, et ou l'on peut facilement garer sa voiture de location et quand on connaît les difficultés de stationnement sur l'île, ce n'est pas négligeable. La voiture de location est nécessaire, mais le village permet un accès à toute l'île par de belles routes et nous avons particulièrement apprécier le calme et la douceur de vivre en rentrant de nos journées sportives, ou l'on croisait beaucoup de monde. Petit supermarché, boulangerie, restos, petit cafés typiques, autant de petits plus qui ont rendu notre séjour hyper agréable. excellent rapport qualité/prix... nous recommandons ++
Superhost
Villa in Sao Vicente
4.76 out of 5 average rating, 92 reviews

Casa junto ao mar

EthanRating, 5 stars2 days ago
Really enjoyable stay in a stunning location. House and outside was perfectly clean and comfortable. The host was very friendly and accommodating - even helped fix our car when it broke down! Would definitely recommend staying here
Top guest favourite
Villa in Santa Cruz
4.97 out of 5 average rating, 76 reviews

Sunrise Bay Balcony

ChangwenRating, 5 stars4 days ago
We really enjoyed our stay at Rui's beautiful home! We were in awe of the view the moment we arrived. The house was in pristine condition and looked exactly as in the pictures. Our family of 5 was very comfortable. Rui also left lots of goodies for us, which was appreciated, since we arrived late in the evening. There was also lots of books and toys that our kids played with everyday before and after we went to explore the island. I would not hesitate to come back and would definitely recommend it to anyone thinking of booking!
Guest favourite
Villa in Ponta do Sol
4.95 out of 5 average rating, 21 reviews

Luxury Haven: Heated Pool, AC & Sun

WilliamRating, 5 stars3 weeks ago
One of the best I’ve ever stayed at. The place was so spacious and open, yet felt like at home and cozy. Everything we needed was readily available/ easily accessible. The home is perched up in Ponta do Sol, so the view is of the homes below, and then the drop off to the ocean. Private pool was clean and big enough for our family of 7. Private parking is a gamechanger anywhere in Portugal, and you have a whole driveway which fit our enormous van. Lots of good hikes in every direction so you never feel like you’re driving too much, everything is about 40 minutes from this location, even the other side of the island. Host was so great responsive despite the hour difference from where she is located. Thank you so much for our stay we loved it.

Luxury villa rentals

Top guest favourite
Villa in Funchal
5 out of 5 average rating, 31 reviews

Villa Vera Downtown

MaryRating, 5 stars1 month ago
Our first visit to Madeira and we had a great time. The villa is immaculate, plenty space, very clean and comfortable and equipped with everything you could need. It’s in a great location to explore Funchal and the wider island. There’s quite a hill to climb on the way back up from the town but it was manageable for a group of 65-75 year olds. And if you decide not to walk Bolt taxis are easily available and not expensive. Nuno and Rubina are excellent hosts. Nuno had sent us lots of information before our trip. Very helpful as we were only there for a week so could make some plans in advance. He came to meet us when we arrived to show us where everything was. Any questions were answered quickly with helpful replies. All of the things Nuno suggested that we tried were very good. I would add an evening at Sabor a Fado to his list of places to try. We had a great night there, but it’s a small place so definitely book. I would highly recommend a stay at Nuno and Rubina’s. Excellent!
Superhost
Villa in Prazeres
5 out of 5 average rating, 3 reviews

Villas Fauna & Flora - Nature & Tranquility - Infinity Pool

ThierryRating, 5 stars10 months ago
The property easily lives up to the description and the pictures. The houses are fully equipped, very nicely decorated and comfortable. The swimming pools offer stunning unobstructed views of the ocean during the day and of the sky at night. There are no road noises, the place is truly calm. Grocery stores are a few minutes away by car, as are restaurants. Numerous hikes can be found in the region. The host is very reactive and will provide many recommandations related to restaurants and activities. Renting both houses to two families is a great way to spend time together while also having some privacy. I would go back there without any hesitation.
Guest favourite
Villa in Ribeira Brava
4.82 out of 5 average rating, 28 reviews

Luxury villa for 6 to 8 people, full ocean view

KennethRating, 5 stars3 months ago
Karine and her family have been super sweet and helpful. We were a family of 6 spanning several generations, and the house is perfect for this. Highly recommended. Everything was new and worked flawlessly. Best recommendations from Kenneth.
Superhost
Villa in Sao Goncalo
4.79 out of 5 average rating, 77 reviews

Casa Crerital - By Wehost

MiguelRating, 5 stars1 month ago
A casa está extremamente bem localizada, numa zona tranquila e com uma vista deslumbrante para o mar. É o local ideal para descansar e aproveitar a paisagem. A casa está equipada com tudo o que é necessário para uma estadia confortável e sem preocupações. Foi uma excelente experiência — recomendo vivamente!
Top guest favourite
Villa in Funchal
4.99 out of 5 average rating, 84 reviews

The Bay House.:full ocean and Funchal bay view

BarbaraRating, 5 stars1 week ago
Sehr empfehlenswert, da traumhafte Aussicht aufs Meer und Funchal. Sehr ruhig gelegen. Äusserst grosszügige Unterkunft mit viel Platz und Stauraum. Eigene Auffahrt mit gedecktem Parkplatz. Für uns zu zweit kostenmässog am oberen Limit, wir bereuen aber keine Sekunde, die letzten Tage/Nächte unserer Madeira Reise dort verbracht zu haben. João hat auf unsere Anreisezeit sehr flexibel reagiert, Danke dafür!
Superhost
Villa in Funchal
4.95 out of 5 average rating, 21 reviews

Amazing villa FUNCHAL, panoramic sea view

CathyRating, 5 stars34 months ago
Nos hôtes, Jeanne et Cristiano, nous ont réservé un accueil chaleureux, avec des produits locaux à notre arrivée ! La maison est très bien située sur les hauteurs de Funchal, avec une vue incroyable sur l'océan (y compris depuis la douche italienne !). La piscine était très agréable (étant frileux, nous avons choisi de la chauffer), la cuisine parfaitement équipée, les chambres très spacieuses et confortables .... Nous avons aussi aimé la déco, les livres (notamment la collection de guides sur Madère en français !)... Tout était parfait, nous avons adoré notre séjour !
Superhost
Villa in Fajã da Ovelha
5 out of 5 average rating, 3 reviews

Blue Sea Tower & Guest Villa. Private Heated Pool

AgneesRating, 5 stars5 months ago
Blue Sea Tower & Guest Cottage w Fajã da Ovelha to wyjątkowe miejsce, które oferuje niepowtarzalne doświadczenia. Położone wśród zapierających dech w piersiach krajobrazów, zapewnia gościom ciszę i spokój, z dala od miejskiego zgiełku. Obiekt łączy nowoczesne udogodnienia z urokiem tradycyjnej maderskiej architektury, a jednocześnie oferuje spektakularne widoki na ocean i góry. Pokoje są przestronne, komfortowe i urządzone w wysokim standardzie, a sama przestrzeń jest bardzo dobrze wyposażona, co sprawia, że pobyt staje się prawdziwą przyjemnością. Dodatkowym atutem jest podgrzewany basen, który pozwala cieszyć się relaksem przez cały rok, niezależnie od pogody. Właściciele i personel są niezwykle gościnni, dbając o każdy szczegół, aby goście czuli się jak w domu. Blue Sea Tower & Guest Cottage to idealne miejsce dla osób szukających odpoczynku w otoczeniu natury, a jednocześnie ceniących komfort, wysoką jakość obsługi i dodatkowe udogodnienia. To prawdziwa perła na mapie Madery!
Superhost
Villa in Funchal
4.71 out of 5 average rating, 7 reviews

Heated Pool • Gym • BBQ • Luxury • Outdoor Dining

AdriannaRating, 5 stars2 months ago
Beautiful house overlooking Funchal & ocean. House was well equipped with everything you may need during your stay (pool towels, baby high chair, gym equipment, fresh linens & very well stocked kitchen appliances). Short drive to shops & restaurants. The house is on a steep hill, you will likely need a car to get around town. Host was responsive and communicative. Would stay again.

Villa rentals with a pool

Guest favourite
Villa in Prazeres
4.8 out of 5 average rating, 10 reviews

Maison vue mer piscine d'eau salée chauffée

FerencRating, 5 stars1 month ago
Tökéletes hetet toltottunk Didier csodalatos házában es nagyon jól éreztük magunkat! Nagyon jól átgondolt, jól felszerelt, tiszta ház volt, minden igényt kielegitoen a konyhától, furdoszoban at a 29 fokra felfutott medenceig! Meg gym matrac, kettlebell, meg petanque is volt! 😉 Nagyon könnyű volt bejutni, idokorlatozas nélkül, nagyon részletes, érthető leírással, könnyű, ingyenes parkolással, akar 2 kocsi részére is. Nagy terekkel, nagyobb családoknak is tökéletes választás! Didier mindig gyorsan válaszolt, segitokesz, barátságos volt!
Villa in Estreito da Calheta
5 out of 5 average rating, 3 reviews

Lake House

JulienRating, 5 stars2 months ago
De hosts van deze fantastische plek hebben ons heel fijn ontvangen. Na een rondleiding door het mooie huis en de tuin, lieten ze de accommodatie aan ons om van te genieten. Ze hebben aan alles gedacht en er is zoveel in het huis aanwezig om een onbezorgde vakantie te hebben. Er stonden lokale lekkernijen klaar voor het hele gezin. We konden niets verzinnen wat beter kan en hebben genoten van ons verblijf. De omgeving is erg goed te verkennen vanuit deze plek en in de middag/avond is het dan fijn thuis komen in dit huis. Bedankt jullie beide!
Superhost
Villa in Arco da Calheta
4.9 out of 5 average rating, 71 reviews

SUNNYSIDE VILLA

CathyRating, 5 stars3 weeks ago
Nous avons passé un excellent séjour dans la Villa de Carmina. Tout était parfait. La maison dispose de toutes les fonctionnalités nécessaires à la réussite de nos vacances en famille. La piscine est un réel atout. Merci à Carmina pour le petit déjeuner d'arrivée.
Guest favourite
Villa in Madeira
4.97 out of 5 average rating, 37 reviews

Design-Villa by the sea/The Banana House

BenRating, 5 stars4 weeks ago
Great location, very peaceful. Fantastic getaway! Hopefully we’ll be back again!
Guest favourite
Villa in Ponta do Sol
4.89 out of 5 average rating, 18 reviews

Heaven's Nest by LovelyStay

MetteRating, 5 stars8 months ago
Yderst attraktiv luksus villa med udsigt over havet. Rummelige værelser og mulighed for opvarmet pool. Vi følte os godt hjemme og kommer helt sikkert tilbage til dette skønne sted på Madeira.
Top guest favourite
Villa in Campanário
5 out of 5 average rating, 6 reviews

Arbor Villa: Nature Retreat

WilRating, 5 stars2 days ago
Where to begin with Arbor Villa? I'll start by saying that it surpassed all our expectations and was far and away the best AirBnb stay we have ever experienced. About the home - It is stunning , luxurious, and welcoming with all the comforts of home. The design is impeccable. Emma and the architect/designers thought of everything and there was no detail overlooked. The materials, color palettes, furnishings, art and decoration combined with the beautiful setting in Campanario create an experience that is in harmony with nature and create a serene and relaxing environment. After long days of exploring the island and hiking the PR's it was so wonderful to come home to this beautiful sanctuary. And the view - Breathtaking. Then there's Emma, our superb host. Her care and attention to detail is second to none. She was forthcoming with excellent recommendations and accommodated our requests to make our stay even more special. She has elevated the AirBnb experience. Highly recommend!
Guest favourite
Villa in Calheta
5 out of 5 average rating, 8 reviews

Villa Gia: Your Home Away from Home

ChristianRating, 5 stars5 days ago
Hands down one of the best Airbnbs I’ve ever stayed at. The property was spotless and the view is unreal. Incredibly peaceful and great for a recharge. A rental car is properly your best bet for getting around the area, although you can get lucky and find Ubers occasionally. There is a parking spot available with a gate to enclose the property. That said, the area is incredibly safe and tranquil. Henrique was incredibly responsive, which I greatly appreciated. Overall, an amazing time. I highly recommend the place to anyone coming to Madeira.
Guest favourite
Villa in Raposeira Do Logarinho
4.91 out of 5 average rating, 32 reviews

Raposeira 22 - Moradia com piscina

AnneRating, 5 stars2 weeks ago
We had a wonderful holiday at Zé Carlos’s place. The house is as described, spacious, clean, comfy beds and everything you need from extra pool towels to shower gel and fully equipped kitchen. Zé Carlos was very reactive and helpful in his communication. The location is peaceful with beautiful views of the mountains and the ocean. We could reach the best hikes, beaches and natural pool all in about 30 minutes drive. The pool is big and clean, we were end of May and used it every single days. We absolutely loved it and hope to come back to Madeira one day!

Quick stats about villa rentals in Calheta

  • Total rentals

    40 properties

  • Nightly prices starting at

    $103 SGD before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Portugal
  3. Madeira
  4. Calheta
  5. Villa rentals