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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.
Superhost
An outdoor dining area is presented, featuring a table set for four, accompanied by dishes and glassware. A vase with flowers adds a touch of greenery. The expansive view showcases the village and ocean, with a clear blue sky forming the backdrop.
Villa in Arco da Calheta
4.74 out of 5 average rating, 27 reviews

Villa with pool in a wooded setting with sea view

CelineRating, 5 stars3 weeks ago
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
Superhost
The exterior of the villa is shown, featuring a modern two-story structure with large windows and a welcoming front entry. A neatly landscaped area includes a vibrant red flowering plant and decorative stones, while lush greenery is visible in the background under a clear blue sky.
Villa in Funchal
4.93 out of 5 average rating, 14 reviews

Allure Alannas Villa by LovelyStay

AlexRating, 5 stars1 month ago
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.
Top guest favorite
A large white villa is surrounded by palm trees, featuring an outdoor pool with clear blue water. The house displays spacious windows, allowing natural light to illuminate the interior. A patio area with lounge chairs is visible, inviting guests to relax in the peaceful garden.
Villa in Funchal
4.93 out of 5 average rating, 75 reviews

Luxury Villa in City Center Private Pool & Rooftop

DavidRating, 5 stars2 weeks ago
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.
Superhost
A private swimming pool is framed by a wooden deck, surrounded by lush tropical plants and flowers. The villa's modern exterior stands nearby, with large windows allowing natural light. A scenic view of the hills and coastline can be seen in the distance under a clear sky.
Villa in Arco da Calheta
4.79 out of 5 average rating, 14 reviews

Villa Nunes, Big Holiday house with private pool

TomiRating, 5 stars6 days ago
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.
Superhost
An expansive coastal view captures the charming village nestled between lush green hills and the Atlantic Ocean. The coastline is dotted with colorful houses, and the vibrant hues of the sea contrast against the clear blue sky with wispy white clouds.
Villa in Paul do Mar
4.8 out of 5 average rating, 45 reviews

New! OCEAN PARADISE Beach Villa 100M from beach

JulieRating, 5 stars3 weeks ago
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 ++
Guest favorite
A suspended orange and white hammock is positioned on a wooden terrace, offering sweeping views of the sea and surrounding landscape. Clear skies and sunlight enhance the tranquil atmosphere, inviting relaxation in this serene outdoor space.
Villa in Estreito da CalhetaCalheta
4.93 out of 5 average rating, 42 reviews

Beautifully presented Villa in stunning location.

MarcRating, 5 stars2 months ago
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.
Guest favorite
An inviting outdoor space features a heated pool, surrounded by a spacious patio. Comfortable lounge chairs are arranged nearby, and a glass railing offers unobstructed views of the serene sea and hillside. Lush greenery is visible in the background, enhancing the tranquil setting.
Villa in Estreito da Calheta
4.97 out of 5 average rating, 61 reviews

Geo Calheta with Swimming Pool and Jacuzzi

KarlyRating, 5 stars1 month ago
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

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, 17 reviews

Ohana Ocean View by LovelyStay

MarieRating, 5 stars2 months ago
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.
Guest favorite
A modern living room is presented, featuring a spacious sectional sofa in light gray. Large glass doors open to a panoramic view of the ocean and Funchal, allowing natural light to illuminate the space. A decorative wall clock and a small plant add subtle accents.
Villa in Funchal
4.96 out of 5 average rating, 26 reviews

Luxury views w/climate control, parking, dryer

TrudyRating, 5 stars2 months ago
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.
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.
Superhost
The villa features a modern architectural design with large windows and a vibrant red roof. A spacious swimming pool is encompassed by a well-maintained terrace, furnished with lounge chairs and umbrellas. Lush greenery surrounds the property, enhancing the private outdoor space.
Villa in Sao Goncalo
4.8 out of 5 average rating, 76 reviews

Casa Crerital - By Wehost

MiguelRating, 5 stars2 weeks ago
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!
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, 83 reviews

The Bay House.:full ocean and Funchal bay view

KristenRating, 5 stars1 month ago
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.
Superhost
A panoramic view of the villa and guest cottage illustrates scenic ocean vistas. The outdoor setting features a large pool and well-maintained gardens, with wooden deck chairs arranged for relaxation. The whitewashed buildings exhibit traditional architecture adorned with terracotta roofs.
Villa in Fajã da Ovelha
5 out of 5 average rating, 3 reviews

Blue Sea Tower & Guest Villa. Private Heated Pool

AgneesRating, 5 stars4 months ago
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!
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
An aerial view showcases a private infinity pool surrounded by a patio area. Lounge chairs and sun umbrellas are arranged on the terrace, bordered by vibrant greenery. The layout emphasizes the connection between outdoor relaxation spaces and the luxurious villa.
Villa in Funchal
5 out of 5 average rating, 5 reviews

Islander - Funchal Seaside Villas

JonathanRating, 5 stars2 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

Villa rentals with a pool

A vintage car sculpture is placed on the lush green lawn, surrounded by the garden. The two-story villa stands in the background, featuring a light exterior with multiple windows and a terracotta roof. A paved pathway leads to the entrance against a scenic mountain backdrop.
Villa in Canhas
4.75 out of 5 average rating, 4 reviews

Villa Retiro

PawelRating, 5 stars12 months ago
Fantastic to stay in really beautifull area. The villa had plenty of rooms and was spotless. Hosts very kind and helpfull highly recommended :))
The exterior view of the modern house reveals large glass doors leading to a private pool. The pool is surrounded by sun loungers and features a backdrop of lush green hills. Large balconies offer seating areas with impressive views of the landscape.
Villa in Arco da Calheta
5 out of 5 average rating, 8 reviews

Luxury Villa Bianca by Holiday Rental Madeira

АнастасияRating, 5 stars3 weeks ago
Perfect quiet location with everything needed for pleasant stay. Sunset view is 10/10!!
Guest favorite
Villa in Ponta do Sol
5 out of 5 average rating, 5 reviews

Villa Mar Lindo - Sea View Lombada Ponta Do Sol

NickyRating, 5 stars11 months ago
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 !
Guest favorite
A spacious villa is depicted with a large pool in the foreground. Sun loungers with blue towels are arranged around the pool area, complemented by an umbrella providing shade. The villa features multiple balconies and windows, contributing to a relaxed outdoor atmosphere.
Villa in Ribeira Brava
4.86 out of 5 average rating, 14 reviews

Villa Fanny, beautiful house with pool.

JulienRating, 5 stars3 weeks ago
Amazing accommodation, with great ocean views. Friendly, available, and responsive host. I would recommend it without second thought:-)
Guest favorite
An inviting outdoor area features a private infinity pool surrounded by colorful plants and potted palms. The pool is framed by modern stonework, and sunlight reflects off the water, enhancing the peaceful setting. The villa’s exterior displays a vibrant color that complements the serene surroundings.
Villa in Funchal
4.85 out of 5 average rating, 26 reviews

VILLA Valhalla Private heated swimming- pool

FlorianRating, 5 stars2 weeks ago
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 ☺️
Guest favorite
A private swimming pool, surrounded by a sun terrace, reflects the clear blue sky and the shimmering sea. Tall cypress trees stand nearby, and colorful planters are positioned around the pool area. A retractable awning provides shade over one side of the pool.
Villa in Caniço
5 out of 5 average rating, 9 reviews

Villa Hansen - Pool, Sea-views, Beach, Garden, BBQ

ThomasRating, 5 stars19 months ago
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
An outdoor terrace features a modern pool surrounded by sun loungers and an umbrella. Floor-to-ceiling glass doors provide a view into the spacious living area. The backdrop showcases the hillside with homes and greenery, creating a relaxed setting for leisure.
Villa in Arco da Calheta
4.77 out of 5 average rating, 13 reviews

Villa Calheta Charm by Villa Plus

JacekRating, 5 stars2 months ago
Beautiful house, amazing view, great location. The host super professional, easy contact. 5 stars! Thank you
The exterior of the villa is showcased, featuring a light-colored facade with decorative tiles. A spacious terrace extends from the upper level, framed by iron railings. Palm trees are positioned near the entrance, and a view of the sea is visible in the background.
Villa in Arco da Calheta
4.75 out of 5 average rating, 4 reviews

Villa Lamayer - Stunning Ocean Views, Private pool

JulienRating, 5 stars21 months ago
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

Destinations to explore

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