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Holiday Rentals with Pools in Estreito da Calheta

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    Travellers to Estreito da Calheta are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    30 Matching Rentals in Estreito da CalhetaView all 59 rentals
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    Calheta Heights1 / 18
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Villa Pinheira III1 / 83
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Villa Rouge1 / 27
    (4)Very good
    3 Bedrooms, 6 Bathrooms, Sleeps 6 Quick View
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    Rosemary Cottage1 / 24
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • Grill
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    Finding the right accommodation can make or break a trip - we knew from the the moment Heather greeted Sue & I, after a long day travelling - that Rosemary Cottage was perfect...
    Reviewed 16 October 2015
    For self-catering accommodation, it would be difficult to find anything superior at anything like this price. The cottage has a superb location on a terrace overlooking the...
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    About this property
    Gulf Stream waters lap the shores of Madeira resulting in fantastic summers and mild winters making the island an exquisite holiday destination all year round. Our spacious cottages enjoy a privileged location in Estreito da Calheta which is to be found on the sunny west coast of this idyllic...
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    9370 221, Estreito da Calheta, Calheta
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Banda do Sol Self Catering - LAVENDER COTTAGE1 / 12
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Mountain Views
    • Internet Access
    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 2017
    We stayed in Lavender cottage, a two bedroom, two bathroom cottage, for a week in September 2017.The cottage is beautifully appointed, very clean, of a very high standard and...
    Reviewed 13 May 2015
    It's a very good Place to relax and we felt from the beginning like at home.the clean Bungalow is well equipped and in the kitchen you'll find everything.the view from the...
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    About this property
    Our spacious cottages enjoy a privileged location on the sunny west coast of the island. Each cottage has its own private terrace and the panoramic views are spectacular! All the windows and glass doors are double glazed with comfort in mind. Within walking distance there is a mini market, a...
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    9370 221, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Lavender Cottage1 / 18
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Grill
    • Ocean Views
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2015
    This was our second visit to Madeira, and it will not be the last. We have rented many cottages over the years, in different parts of Europe. Lavender Cottage was no doubt the...
    Reviewed 28 December 2014
    Heather and her family were really welcoming and gave plenty of tips and advice on how to maximise our short week on the island. She certainly goes the extra mile. Thank you...
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    About this property
    Gulf Stream waters lap the shores of Madeira resulting in fantastic summers and mild winters making the island an exquisite holiday destination all year round. Our spacious cottages enjoy a privileged location in Estreito da Calheta which is to be found on the sunny west coast of this idyllic...
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    9370 221, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casa Palheiro at Casas Da Vereda1 / 53
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Housekeeping Included
    • Mountain Views
    • Cable/satellite TV
    • Patio
    • Ocean Views
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 November 2017
    We spent the week here for our honeymoon, with 3 kiddies at home and another on the way we wanted somewhere we could really relax and make the most of our last week of adult...
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    About this property
    Relax in Class at 200m high on the Sunny South West Coast of Madeira and enjoy the Sunset and Ocean View from the Pool! You can rent Casa Palheiro - studio, Casa Rural - 1 bedroom, Casa Eco - 2 bedrooms, or any combination. Have a look on the Picture Galleries to make sure that you select the best...
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    9370 225, Estreito da Calheta, Calheta
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Modern luxury 4 bed house with large pool and gard1 / 20
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 November 2016
    We had a fantastic holiday at villa frangipani, we were a group of 8 and did not feel crowed at all as the house is very spacious. The house really was a lot better then we...
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    About this property
    4 bedrooms, 3 bathrooms, separate WC, sleeps 8 Casa Frangipani is an outstanding modern villa standing on a large level site in the hamlet of Estreito da Calheta on the south-west coast of the beautiful sub-tropical island of Madeira. Designed in a contemporary style by Miguel Santos of the...
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    9370 239, Estreito da Calheta, Calheta
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Ocean Views
    • Balcony
    • Washer
    • Mountain Views
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern, self-catering penthouse apartment situated amongst the quiet banana groves of Calheta, with magnificent views of the sea,beach, Marina, and the hills.Overlooking the center of Vila da Calheta with its beautiful golden sandy beaches,this apartment is in a few minutes walking distance to...
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    9370 146, Estreito da Calheta, Calheta
    Holiday Rental House - 1 Bathroom, Sleeps 4
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    Cliffscape1 / 26
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 December 2017
    We were a party of four and had a wonderful week in Maderia. The villa is perfect. Modern and spacious and with everything you need. The expansive terrace and pool area had...
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    About this property
    With outstanding panoramic sea-views and offering privacy and seclusion, surrounded by tranquil countryside, Cliffscape is a superb quality air-conditioned villa with heated pool that fully lives up to its name, with the great advantage that it is located in the sunniest area of Madeira and only...
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    Location Information
    9370 268, Estreito da Calheta, Calheta
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Ocean Views
    • Washer
    • Wi-Fi
    • Balcony
    • Mountain Views
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Don't be fooled by the photos. This villa is even more charming than it looks! A high class build with a location that is postcard perfect! The villa is part of small suburban development that has all the modern amenities of a top class neighborhood! This house is for leisure and comfort. Being a...
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    9370 145, Estreito da Calheta, Calheta
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Parking
    • Washer
    • Wi-Fi
    • Ocean Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Atlântico is a luxurious modern property located in the tranquil and sunny Calheta. With 650 m² this stunning villa has heated swimming pool, free Wi-Fi, a surrounding garden, barbecue, 3 spacious bedrooms, modern kitchen, elegant living room and a fantastic view to the Atlantic Ocean....
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    9370 763, Estreito da Calheta, Calheta
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    VILLA SAPATINHO - POOL, SEA VIEW, WIFI, BBQ1 / 18
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Mountain Views
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    9370 227, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Cable/satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedroom typical Madeiran villa cottage in stone rocks with glass pool, big barbecue room with table, modern full kitchen, 1 bathrooms, garden, 5 min to Calheta sand golden beach, close to walking nature levadas, 25 min to Funchal centre, 45 min to the airport. A real living Madeira Island style....
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    Location Information
    9370 058, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Mountain Views
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The pet-friendly Paraíso das Flores offers self-catering villas in Estreito da Calheta, between the picturesque villages of Calheta and Jardim do Mar, Madeira Island. It includes an outdoor swimming pool. The modern 3 self-catering villas offer panoramic views of the surrounding landscape. The...
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    9370 227, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Mountain Views
    • Cable/satellite TV
    • Patio
    • Washer
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    9370 253, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Terrace
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 2 bedroom super 'Penthouse' apartment located in Calheta in a small, quiet and privat building. The property has 2 generous bedrooms, 2 luxurious bathrooms and a modern kitchen with laundry area etc... The property was recently decorated with high quality furniture which is extremely...
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    9370 146, Estreito da Calheta, Calheta
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Ocean Views
    • Washer
    • Patio
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    located in a pleasant area of Calheta, with a fantastic view over the sea and the mountain. The house is composed by: Ground-floor - room where clients have at its disposal a washing machine, as well as a football table.2 double bedrooms ,2 twin bedroom 1 single room sitting room with kitchenette...
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    9370 249, Estreito da Calheta, Calheta
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    VILLA ORCHID - POOL, SEA VIEW, WIFI, BBQ1 / 18
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Central Heating
    • Mountain Views
    • Washer
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    9370 227, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    • Balcony
    • Ocean Views
    • Mountain Views
    • Housekeeping Included
    • Cable/satellite TV
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in Class at 200m high on the Sunny South West Coast of Madeira and enjoy the Sunset and Ocean View from the Pool! You can rent Casa Palheiro - studio, Casa Rural - 1 bedroom, Casa Eco - 2 bedrooms, or any combination. Have a look on the Picture Galleries to make sure that you select the best...
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    Location Information
    9370 225, Estreito da Calheta, Calheta
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Vivenda rustica da calheta1 / 17
    (3)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Balcony
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    O chalé rústico construído com pedras naturais foi construído no estilo típico de quinta madeirense com um ambiente acolhedor e confortável. A casa fica perto de uma pequena estrada nas colinas superiores da Calheta cercado por típicos quintas madeirenses. o carácter rústico da casa é sublinhada...
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    9370 159, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Grill
    • Balcony
    • Washer
    • Wi-Fi
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    9370 237, Estreito da Calheta, Calheta
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Mountain Views
    • Ocean Views
    • Washer
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a pleasant area of Calheta, with a fantastic view over the sea and the mountain. The house is composed by: Ground-floor - room where clients have at its disposal a washing machine, as well as a football table.2 double bedrooms ,2 twin bedroom 1 single room sitting room with kitchenette...
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    9370 249, Estreito da Calheta, Calheta
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Wi-Fi
    • Grill
    • Patio
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a pleasant area of Calheta, with a fantastic view over the sea and the mountain. The house is composed by: Ground-floor - room where clients have at its disposal a washing machine, as well as a football table.2 double bedrooms ,2 twin bedroom 1 single room sitting room with kitchenette...
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    Location Information
    9370 249, Estreito da Calheta, Calheta
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Secure Parking
    • Washer
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    9020 000, Estreito da Calheta, Calheta
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Washer
    • Housekeeping Included
    • Balcony
    • Grill
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in Class at 200m high on the Sunny South West Coast of Madeira and enjoy the Sunset and Ocean View from the Pool! You can rent Casa Palheiro - studio, Casa Rural - 1 bedroom, Casa Eco - 2 bedrooms, or any combination! Have a look on the Picture Galleries to make sure that you select the best...
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    9370 255, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Secure Parking
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    9370 255, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Paraiso Das Flores1 / 12
    (1)Terrible
    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Ocean Views
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect place to relax and unwind from your daily routine... Located in the south west of the Island of Madeira, in the village of Estreito da Calheta in the rural country side; surrounded by vineyards, sugar cane and farmland is where you will find Paraiso das Flores. The 3 independant...
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    Location Information
    9370 227, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Ocean Views
    • Balcony
    • Secure Parking
    • Terrace
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located less than 5 minutes away from the Calheta beach, this gorgeous villa, winner of the 2016 Luxury Travel Guide Award has everything to make your holiday memorable. Spread around 900 m² this modern and luxurious property offers a spacious terrace, garden, a large heated swimming pool, free...
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    9370 143, Estreito da Calheta, Calheta
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Mountain Views
    • Wi-Fi
    • Grill
    • Terrace
    • Parking
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fantástica casa reconstruida, Piscina com uma vista infinita para o mar. A área possui um bom acesso ao mar, e a beleza natural do litoral, tornando-o o local de escolha para férias e residências permanentes afins. Calheta também serve como ponto de partida para vários passeios de montanha, com...
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    Location Information
    9370 159, Estreito da Calheta, Calheta
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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