
Villa holiday rentals in Calheta
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Top-rated villa rentals in Calheta
Guests agree: These villas are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Calheta villa rentals
Private villa rentals

Villa Fedra - A hidden paradise
Lovely garden and my daughter loved picking oranges herself and squeezing them to juice for breakfast.

Quinta Marefe - On the stunning west coast
This is how AirBNB should be. The house is stacked with everything. How often are you in an Airbnb and they only have 6 plates? Here they have 20+, they have Great knives, tons of kitchenware, enough toilet paper, plenty of dishwasher tabs and also cleaner for the washing machine. Things you normally expect but somehow got lost in the making money machine Airbnb is now. Not here!! A absolute crazy welcome basket (have not had such a big one ever), friendly crew and absolute amazing place - can only recommend

Paradise views - Pereira House
We have just returned from a week's vacation in Luis' accommodation. Impeccable house, nothing to say about the cleanliness! Everything matched the description of the listing! Only small improvements: the lack of storage to put things in the bedrooms and bathroom, and a drying rack a little small given the capacity of the house! Otherwise, our stay was perfect, the house and its view were great! We would highly recommend this place!

Ohana Ocean View by LovelyStay
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!

Morning Glory - Penthouse
Very pretty and big apartment, with a great balcony and ocean view. A lot of furniture. Marlene was very responsive. The town is super close by car (5 min) and very enjoyable. It is very calm, however they are building some houses in front of the apartment, starts quite early even the Saturday… Except this detail we enjoyed our stay very much. Thank you !

The Old Caboz House
we’ve had an amazing experience staying at this place! the view is great, location is easy to find. house is extra clean and well equipped. Beatriz was always answering immediately and ready to help. thank you for having us 🩷

Sunrise Bay Balcony
The accommodation is amazing, a very modern and homely feel with all the amenities that you'd need for a stay in Madeira! Rui went consistently above and beyond to communicate with us his recommendations of things to do, places to go/eat, and to update us on aspects of the accommodation (such as the newly installed BBQ). We'd love to come back soon!

Arbor Villa: Nature Retreat
Well what can I say about abor villa- By far the best air bnb we have ever stayed in. Absolutely exceptional and decorated beautifully, so artistic and clean and akin to a boutique hotel. Emma was a fantastic host, she made the whole stay exceptional for our young family. Personal touches such as a mini chair for our two year old with suitable cutlery, cups etc ready for us, even taking the trouble to remove the legs of the children’s bed so not too high from the ground. She provided a box of toys for our children and ensured staples were ready for us after a late flight so that the children had food and milk- something we whole heartedly appreciated. The position of the villa was ideal- close to the capital, excellent views , close to restaurants and local towns and ideally situated so easy to get to the northern sites of the island which really wasn’t far when renting a car. Emma was easily reachable and offered lots of recommendations. The pool and views exceptional, we will return!
Luxury villa rentals

Villas Fauna & Flora - Nature & Tranquility - Infinity Pool
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.

Casa Crerital - By Wehost
The house is extremely well located, in a quiet area with a stunning sea view. It is the ideal place to rest and enjoy the scenery. The house is equipped with everything needed for a comfortable and worry-free stay. It was a great experience — I highly recommend it!

The Bay House.:full ocean and Funchal bay view
Fantastic views, really quiet but easy to get to places. Great villa, would be happy to stay again when next in beautiful Madeira

Amazing villa FUNCHAL, panoramic sea view
Beautiful, clean, open and inviting home! Jeanne and her family were wonderful hosts! Quick and easy trip into Funchal but so nice to have the privacy! Thank you so much!!

Blue Sea Tower & Guest Villa. Private Heated Pool
Blue Sea Tower & Guest Cottage in Fajã da Ovelha is a unique place that offers a unique experience. Nestled amongst breathtaking landscapes, it provides guests with peace and quiet, away from the hustle and bustle of the city. The property combines modern amenities with the charm of traditional Maderian architecture while offering spectacular ocean and mountain views. The rooms are spacious, comfortable, and decorated to a high standard, and the space itself is well-equipped, which makes your stay a real pleasure. An additional advantage is the heated pool, which allows you to enjoy relaxation all year round, no matter the weather. The owners and staff are extremely welcoming, taking care of every detail so that guests feel at home. Blue Sea Tower & Guest Cottage is the perfect place for those seeking a respite surrounded by nature, while appreciating comfort, high quality service, and additional amenities. It's a real pearl on Madeira's map!

Islander - Funchal Seaside Villas
We stayed at Patricia’s villa for 9 days and had a great time. The view overlooking the ocean with the infinity pool was beautiful! We loved waking up to this gorgeous view each morning. It was also a plus that we had the use of house cleaners that came during our stay to make the place extra tidy after we stayed halfway through! All the balcony’s outside connected and lead directly to the downstairs pool. There’s also a “secret” access to the bottom of the cliff which was very cool! Everything was perfect! All in, I’d give this a 5 star stay, everyone was extremely happy and we would definitely stay again in the future! Thank you for hosting us

Luxury Haven: Heated Pool, AC & Sun
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.

Heated Pool • Gym • BBQ • Luxury • Outdoor Dining
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

House with sea view and heated saltwater pool
We had a perfect week in Didier's wonderful house and had a great time! It was a very well thought out, well-equipped, clean house, from the kitchen to the pool that ran up to 29 degrees! There was also a gym mattress, kettlebell, and petanque! 😉 It was very easy to get in, without a time series, a very detailed, understandable description, easy, free parking, and want for 2 cars. With large spaces, it's perfect for larger families! Didier was always quick to respond, helpful, friendly!

Lake House
The hosts of this fantastic place welcomed us very nicely. After a tour of the lovely house and garden, they left the accommodation to us to enjoy. They have thought of everything and there is so much in the house to have a carefree vacation. There were local delicacies ready for the whole family. We couldn't think of anything that could be better and loved our stay. The area is very easy to explore from this place and in the afternoon/evening it is then nice to come home to this house. Thank you both!

Luxury Villa Bianca by Holiday Rental Madeira
Fantastic villa. We stayed there as a family of four and loved the accommodation. The villa was spacious, clean and well equipped. The view was incredible looking out to sea from all the bedrooms, the living space and the pool area. The location was wonderful and close to beaches and hiking areas, less than a 20 minute drive to Calheta or the trekking areas in the mountains behind the house. Not really that far to anywhere on Maderia and we also had days out in Porto Moniz and even Canical was less than an hours drive. House was easy to find, check in was easy and hosts were very helpful throughout. Would highly recommend.

Villa Nunes, Big Holiday house with private pool
Big villa for us three tht went would definitely book again and could take the whole family. Lot of room and was an easy home base to explore the island.

Luxury villa for 6 to 8 people, full ocean view
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.

Villa Noelia Ocean View
Amazing property! Loved every moment of the stay. Airbnb fully equipped with everything you need. Marco the host was wonderful and really helped us and made us feel welcomed and offered local spots and helped with everything we needed. Defo recommend and will come back again. Thank you very much for having us

Heated pool, hot & cold AC, BBQ, views & parking
I had a very pleasant and good stay at the Hillside Villa. At arrival I got very well received by Elvio at the villa. He explained everything good and gave some tips and advice for my stay. The communication is very good with Mandy an Elvio. Friendly and respons was fast. They give you the feeling your stay is important to them. The Hillside Villa was very clean and very well equipped. The pool is heated and nice also to use on a bit colder day. The garage is big enough for a medium to big size car. The street to the garage is a bit small but doable. So a bit of a challenge with a big size. Further the outside door space was clean and very useable with different place to seat during the day with sun. The neighbors are very nice people. Thank you for everything Elvio and Mandy.

Villa Casa das Orquídeas with superb sun exposure
Thank you for a wonderful stay. The apartment was beautiful and all the advice and tips were much appreciated and helped our stay.
Quick stats about villa rentals in Calheta
Total rentals
40 properties
Nightly prices starting at
$133 NZD 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
- Porto Santo Holiday rentals
- Ponta do Sol Holiday rentals
- Machico Holiday rentals
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