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Villa vacation rentals in Calheta

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Popular amenities for Calheta villa rentals

Private villa rentals

Superhost
The villa's exterior is showcased at dusk, highlighting its stone facade and charming architecture. Outdoor seating is arranged on the lawn, surrounded by the garden's greenery. Warm light emanates from the windows, creating a welcoming atmosphere as the surrounding landscape is subtly illuminated.
Villa in Calheta
4.87 out of 5 average rating, 89 reviews

Villa Fedra - A hidden paradise

HenningRating, 5 stars6 months ago
Lovely garden and my daughter loved picking oranges herself and squeezing them to juice for breakfast.
Top guest favorite
The villa features a modern two-story structure with large glass doors opening to a patio. A sparkling pool reflects the evening sky, surrounded by stone landscaping and sun loungers. Green mountains provide a serene backdrop, enhancing the peaceful atmosphere of the outdoor space.
Villa in Paul do Mar
5 out of 5 average rating, 16 reviews

Quinta Marefe - On the stunning west coast

FabianRating, 5 stars1 week ago
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
Guest favorite
The exterior view showcases a modern two-story structure with a contrasting orange-tiled roof. A spacious balcony equipped with outdoor furniture overlooks the surrounding landscape. A well-maintained garden borders the property, adding a touch of greenery to the inviting entrance.
Villa in Arco da Calheta
4.88 out of 5 average rating, 16 reviews

Paradise views - Pereira House

LisaRating, 5 stars2 weeks ago
We had a very nice stay! The place was clean, well appointed and exactly as described. The location is quiet and ideal for relaxing. The contact with the host was friendly and straightforward. A small note: A dishwasher would be a helpful addition, and the drain in the bathroom should possibly be checked, as there were occasional problems there. Otherwise everything was wonderful – we would love to come again!
Guest favorite
A private swimming pool is surrounded by sun loungers, offering expansive ocean views. The pool area features well-maintained tiles, and large glass doors lead into the interior of the home, allowing for an abundance of natural light.
Villa in Canhas
4.88 out of 5 average rating, 17 reviews

Canhas Views Pool and Barbecue

Luana BaioniRating, 5 stars4 months ago
This house is a dream coming true! They are the best hosts too. The only bad thing about that house is that I had to leave (lol). I would stay there many many times more. Lots of restaurants and groceries stores close. My family and I loved staying in there.
Superhost
A wooden dining table is set for two on a balcony with a stunning ocean view. Two plates with bread and fruit are arranged alongside a glass of water and a bottle. The mountainsides in the distance complement the serene coastal landscape.
Villa in Estreito da Calheta
5 out of 5 average rating, 8 reviews

Morning Glory - Penthouse

NolwennRating, 5 stars1 month ago
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 !
Guest favorite
A terrace area showcases a glass dining table surrounded by four metal chairs. The view highlights the expanse of the sea under a pastel sky during sunset. Green plants are placed strategically, enhancing the outdoor ambiance.
Villa in Madeira
4.87 out of 5 average rating, 45 reviews

The Old Caboz House

KaterynaRating, 5 stars1 week ago
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 🩷
Superhost
A clear view of a serene salt-water pool surrounded by a sun terrace. A yellow umbrella provides shade for two lounge chairs positioned nearby. The ocean stretches into the horizon, with the sky bright and unobstructed.
Villa in Sao Vicente
4.76 out of 5 average rating, 91 reviews

House by the sea

AnneRating, 5 stars3 weeks ago
The view from the garden was truly beautiful. The cottage is so close to the sea that you could hear the surf in your bedroom. Otherwise, it was very quiet. A wonderful swimming pool and garden with different seats and also sunbeds so you could always choose where you wanted to sit. There was even a BBQ!
Top guest favorite
A serene balcony setting features a glass-top table with two woven chairs, offering a panoramic view of the coastline under a colorful sky at dusk. The horizon showcases subtle hues of orange and purple as the landscape lights begin to twinkle.
Villa in Santa Cruz
4.97 out of 5 average rating, 75 reviews

Sunrise Bay Balcony

BenjaminRating, 5 stars4 weeks ago
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!

Luxury villa rentals

Guest favorite
A modern outdoor space is presented with two hanging chairs positioned on a stone patio, facing the ocean. A private pool is visible in the background, surrounded by manicured grass. Expansive windows reflect the blue sky and enhance the connection to the surrounding landscape.
Villa in Arco da Calheta
5 out of 5 average rating, 18 reviews

Ohana Ocean View by LovelyStay

OliverRating, 5 stars2 weeks ago
This is one of the most beautiful AirBnB's I've ever stayed in. The house itself is modern, clean, spacious and very beautiful. It sits high up in the hills and we were greeted by a stunning sunset when we arrived. You won't be disappointed by the sunset! You definitely need a car to get to this location, but it's only around 10 mins from Arco de Calheta. The host was really responsive, friendly and always willing to help. We really have no complaints about this place!
Superhost
An aerial view reveals a two-story family home featuring a terracotta roof and multiple balconies. Surrounding greenery includes mature palms and shrubs. A spacious outdoor terrace with lounge chairs is seen in the foreground, providing ample space for relaxation and gatherings.
Villa in Funchal
4.92 out of 5 average rating, 37 reviews

Charming Villa, spacious, with beautiful views!

BenoitRating, 5 stars3 weeks ago
Great villa ! Spacious, well equiped, comfortable beds, close to Funchal's center, this was perfect !
Superhost
Two independent villas are positioned harmoniously on a landscaped property. Each villa features an inviting porch and is complemented by infinity swimming pools, surrounded by lounge chairs. A flourishing garden with neatly arranged greenery leads to the edge of the property, enhancing the natural setting.
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.
Top guest favorite
The villa's contemporary exterior features a smooth concrete structure with large glass panels and multiple windows. The building is situated on a hillside, surrounded by greenery and offering unobstructed views. The sunset casts warm light on the facade, enhancing its modern design.
Villa in Funchal
4.99 out of 5 average rating, 84 reviews

The Bay House.:full ocean and Funchal bay view

DavidRating, 5 stars2 weeks ago
Fantastic views, really quiet but easy to get to places. Great villa, would be happy to stay again when next in beautiful Madeira
Superhost
A serene infinity pool offers a panoramic view of the ocean and coastal landscape. Two individuals are seen enjoying the warm waters, with lush greenery framing the scene and the horizon blending into the azure sky.
Villa in Funchal
4.95 out of 5 average rating, 21 reviews

Amazing villa FUNCHAL, panoramic sea view

HeleneRating, 5 stars34 months ago
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!!
Guest favorite
Villa in Funchal
5 out of 5 average rating, 6 reviews

Islander - Funchal Seaside Villas

JonathanRating, 5 stars3 months ago
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
Superhost
A view of the villa showcases an inviting infinity pool in the foreground, surrounded by sunbeds with blue cushions. The two-story villa features large windows and balconies, highlighting the modern design against a clear blue sky.
Villa in Fajã da Ovelha
4.9 out of 5 average rating, 90 reviews

Blue Sea Villa. Private Heated Pool. Garden. Quiet

LauraRating, 5 stars1 week ago
Really enjoyed our stay at blue sea villa. Grandparents loved spending a holiday with the grandkids. Pool was a big hit! The area was very quiet and peaceful. The house itself was well equipped and like a home from home. Thanks for being a great host!!
Guest favorite
A private pool area features a clear blue swimming pool surrounded by stone tiles. Two wooden lounge chairs, adorned with blue and white striped cushions, are positioned beside the pool, inviting relaxation under the sun.
Villa in Ponta do Sol
4.95 out of 5 average rating, 20 reviews

Luxury Haven: Heated Pool, AC & Sun

WilliamRating, 5 stars2 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.

Villa rentals with a pool

Guest favorite
Villa in Prazeres
4.89 out of 5 average rating, 9 reviews

House with sea view and heated saltwater pool

FerencRating, 5 stars3 weeks ago
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!
Villa in Estreito da Calheta
5 out of 5 average rating, 3 reviews

Lake House

JulienRating, 5 stars1 month ago
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!
Guest favorite
A clear view of the infinity pool is framed by lush greenery and vibrant yellow umbrellas. Comfortable seating aligns beside the pool, offering a relaxed atmosphere with stunning views of the ocean.
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.
The image features a modern villa with large glass doors that provide a view of the interior dining area. A sparkling pool is situated in the foreground, reflecting the sky above. Lush greenery is visible in the background, enhancing the tranquil atmosphere.
Villa in Prazeres
5 out of 5 average rating, 4 reviews

Villa Noelia Ocean View

ShaquilleRating, 5 stars1 week ago
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
Guest favorite
A private heated swimming pool is set within a modern exterior. Clear blue water glistens under the sun, surrounded by sleek glass railing. Views of greenery and the distant sea can be seen beyond the pool, contributing to a serene outdoor environment.
Villa in Arco da Calheta
4.93 out of 5 average rating, 208 reviews

Heated pool, hot & cold AC, BBQ, views & parking

RonRating, 5 stars1 week ago
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.
Guest favorite
Villa in Calheta
4.98 out of 5 average rating, 59 reviews

Villa Casa das Orquídeas with superb sun exposure

GillianRating, 5 stars3 months ago
Thank you for a wonderful stay. The apartment was beautiful and all the advice and tips were much appreciated and helped our stay.
Villa in Lombo Do Doutor
4.88 out of 5 average rating, 8 reviews

VILLA CAMACHO - ULTRA LUXURY

TamasRating, 5 stars9 months ago
We have loved every moments in the villa.
Top guest favorite
Villa in Funchal
4.98 out of 5 average rating, 132 reviews

Quinta do Alto

MelanieRating, 5 stars1 month ago
Everything they say is true. If you can find space in Henrique’s crowded calendar, do not hesitate. So much private outdoor space! Our trip was early May and weather was variable, including some rain and a ferocious storm overnight. But we still managed to sit outside by the pool most evenings, just enjoying the exotic surroundings and watching the mist move about over the hills. So peaceful. Indoors is everything you need: the bedroom is large with reading lamps (quite rare in Airbnbs) and a huge wardrobe as well as a desk. The bathroom is also a good size with walk-in rain shower. The kitchen / diner / lounge is also well-equipped (there is a bread knife in the kitchen drawer, another Airbnb rarity) and the wifi works well. Everything top quality and ultra comfortable. We walked both up and down the hills into Funchal (although there is a bus service from right outside the door), as well as up to the Botanical Gardens. A very peaceful setting and a perfect host in every way.

Quick stats about villa rentals in Calheta

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 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