
Villa vacation 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.
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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.

Villa with pool in a wooded setting with sea view
Very good stay, impeccable house on two levels, barbecue with all the accessories, pool out of sight, Quiet place for a good restful night. Recommended

Allure Alannas Villa by LovelyStay
Thoroughly enjoyed our stay. The property was exactly like the description in every way and it often exceeded expectations. Spotlessly clean and amazing views out to sea. I would book again.

Luxury Villa in City Center Private Pool & Rooftop
Really lovely accommodation with great views. The host was very responsive and was super helpful when we had a bit of an emergency. Highly recommended.

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.

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 ++

Beautifully presented Villa in stunning location.
We had a wonderful time at the Villa. It had everything you needed, was comfortable and very quiet. A good supermarket in walking distance a great view over the sea. We can highly recommend this villa and will definetly be back.

Geo Calheta with Swimming Pool and Jacuzzi
Perfect location! The villa is clean, quiet, and well equipped. The pool was such a treat and the views of the ocean are spectacular. The walk into town is only about 20 minutes. The walk back up is steep but doable with young children. The neighborhood is also lovely. It was a great place to stay as a family. We loved our time here and would absolutely book again.
Luxury villa rentals

Ohana Ocean View by LovelyStay
A beautiful place, peaceful and with stunning views. The host Jun pays attention to the details when it comes to the amenities which makes all the difference. It was a perfect, restful stay, would highly recommend.

Luxury views w/climate control, parking, dryer
Just returned from a 4 night stay at Kents apartment with a group of friends. Apartment was spacious with great views over Funchal. The apartment is around 10 minutes taxi drive or bus journey (takes a little longer) from the centre of Funchal or up to the tropical gardens at Monte. There is a little shop for essentials around 10 minutes walk away, just a step hill walk back up. Kent was an excellent communicator from first booking. Would definitely recommend.

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
We had an unforgettable stay at this stunning home in Madeira! The views were absolutely out of this world—waking up to sweeping panoramas of the ocean and Funchal every day felt like a dream. The house itself has a modern, stylish aesthetic that made it feel both luxurious and comfortable. João was an incredibly warm and welcoming host—he made us feel right at home and was always happy to help with anything we needed. Highly recommend this spot if you’re looking for beauty, comfort, and a truly special Madeira experience.

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!

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!!

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
Villa rentals with a pool

Villa Retiro
Fantastic to stay in really beautifull area. The villa had plenty of rooms and was spotless. Hosts very kind and helpfull highly recommended :))

Luxury Villa Bianca by Holiday Rental Madeira
Perfect quiet location with everything needed for pleasant stay. Sunset view is 10/10!!

Villa Mar Lindo - Sea View Lombada Ponta Do Sol
A beautiful house with stunning views, well equipped with plenty of space for everyone. Clive always responded quickly to any requests. The property is within 30mins of Funchal and perfect position to go and explore the coastline and mountains of Madeira Would thoroughly reccomend !

Villa Fanny, beautiful house with pool.
Amazing accommodation, with great ocean views. Friendly, available, and responsive host. I would recommend it without second thought:-)

VILLA Valhalla Private heated swimming- pool
Soraia's villa is a great place to stay in, very good when travelling in group. The house was impeccable, really big and has everything to offer for a great trip (swimming pool, outdoor kitchen, rooftop ..). Ideally located near the center, perfect for visiting Funchal effortlessly. I highly recommend ☺️

Villa Hansen - Pool, Sea-views, Beach, Garden, BBQ
We rented Jan's villa for a week and got to know Jan as an accommodating and great landlord. The house fully met our wishes and ideas and was as described in the listing. We didn't miss anything - except a coffee maker with capsule system. But that is now available ;-) The villa was very clean including all rooms and bathrooms were very clean. We really appreciated it, everyone had their own bathroom and two of the three bedrooms even had pool and sea views. The kitchen is huge and gave us so much pleasure that we never went out to eat the whole week. Another highlight is of course the pool and the lounge with sea views as well as the grill (BBQ). For us as very active athletes, the washing machine was awesome; so we could wash every evening after our sporting activities and didn't have to take so much clothing from home. Long story short; it was just BRILLIANT. Thank you Jan

Villa Calheta Charm by Villa Plus
Beautiful house, amazing view, great location. The host super professional, easy contact. 5 stars! Thank you

Villa Lamayer - Stunning Ocean Views, Private pool
Great stay! Host is very responsive and the person (Yvonne) who manages the property was very friendly. Beautiful villa, magnificent view, peaceful, and very bright! The pool was great! The kitchen is very well equipped and spacious! A real holiday home! We will surely be back to Lauri's if we go back to Madeira!
Quick stats about villa rentals in Calheta
Total rentals
40 properties
Nightly prices starting at
$80 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
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