
Villa holiday rentals in Calheta
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Top-rated villa rentals in Calheta
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Popular amenities for villa rentals in Calheta
Private villa rentals

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

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!

Private House with 2 en-suites - Urban Farm 1
Luna helped us to arrive in the middle of the night, which was fantastic! We even got a small snack that we don't have to go to sleep hungry. The kitchen and terrace are lovingly furnished, so you feel really comfortable. We had nice neighbors who we met at breakfast. In the evening we could easily walk into town. We are glad that we were able to start our Madeira vacation in this cozy place.

New! OCEAN PARADISE Beach Villa 100M from beach
Large house ideal for a family, beautiful kitchen, terrace and sea view. Iva is a welcoming host who takes the time to leave us lots of information to discover this beautiful island. So we were able to discover the dolphins at a preferential and zn price passing through a local agency😊... The accommodation is located in the southwest of the island, in a small quiet fishing village, and where you can easily park your rental car and when you know the parking difficulties on the island, it is not negligible. The rental car is necessary, but the village allows access to the whole island by beautiful roads and we particularly appreciated the calm and sweetness of living when we returned from our sports days, where we met a lot of people. Small supermarket, bakery, restaurants, small typical cafes, so many little extras that made our stay super pleasant. great value for money... we recommend it ++

House by the sea
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

Sunrise Bay Balcony
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!

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.
Luxury villa rentals

Villa Vera Downtown
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!

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.

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.

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!

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!

SUNNYSIDE VILLA
We had a great stay at Villa de Carmina. Everything was perfect. The house has all the features necessary for the success of our family vacation. The pool is a real asset. Thanks to Carmina for the breakfast on arrival.

Design-Villa by the sea/The Banana House
Great location, very peaceful. Fantastic getaway! Hopefully we’ll be back again!

Heaven's Nest by LovelyStay
wonderful place, beautiful views! The house is very modern with great amenities and has everything you need.

Arbor Villa: Nature Retreat
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!

Villa Gia: Your Home Away from Home
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.

Raposeira 22 - Villa with pool
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
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