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Smoking Allowed Holiday Rentals in Oia

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    Travellers to Oia are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    30 Matching Rentals in OiaView all 191 rentals
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    Ninetta's house1 / 16
    (11)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Poseidon Mansion in Santorini1 / 22
    (6)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    By the Mill, Caldera, Oia - private, spacious, sunset and volcano views1 / 31
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Hot Tub
    • Terrace
    • Balcony
    • Ocean Views
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gazing the deep blue, Kalidoscope is a complex of three traditional, fully renovated cave houses ideal for all visitors’ who wish to experience a traditional, modern home accommodation in Santorini. The traditional style houses offer a unique view, a comfortable and warm environment and a...
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    847 02, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    The house of the seven ships1 / 26
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Balcony
    • Ocean Views
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2016
    We loved staying here, it was nice to be a little ways outside of Oia (10 minute walk) where it was nice and quite. It has a great view of the ocean and even walking through...
    Reviewed 22 July 2016
    We thoroughly loved our time ag the House of Seven Ships. The views, location and the cave house itself we're all spectacular. Georgia was our host and she went to great lengths...
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    About this property
    This is a 60 sq m house, with panoramic views over the Aegean Sea and the vineyards of Finikia from the terrace-balcony of 30 sq. m House is composed by the main domed chamber (living-dining room), one domed bedroom, sizeable bathroom and a fully equipped kitchen. The “house of the seven ships”...
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    84702, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Garden
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kalidoscope villas is a complex of three new villas overlooking the unique caldera with the famous volcano of Santorini. Nesstled at the beautiful village of Oia, Kalidoscope complex open its doors to guests for the first time in 2016. Nestled on the cliffs of the worldwide famous village of Oia,...
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    84700, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Wineryhouse where dreams live......1 / 96
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Outdoor Dining Area
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 October 2017
    We had fabulous time at the Red wine house. We were a family of 7 including 2 small kids, and the red wine house accommodated us perfectly.Elini was a superb host who helped...
    Reviewed 13 June 2017
    We had the most wonderful stay in Wineryhouse, Oia. We are a family of three, with a grown up daughter. The villa was perfect in every way. Very quiet and calm. Facilities were...
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    About this property
    An old Winery renovated and transformed into a very stylish villa with amazing oriental garden and a tiny swimming pool Situated in the peaceful and traditional village of 'Finikia' in Oia The Winery House (main domain), part of the 'Winery Villa' complex: This was the last winery which operated...
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    84702, Oia, Santorini
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunny Winehouse1 / 38
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Ocean Views
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2015
    We have spend a week of amazing holiday in the Sunset house. I thought I have dreamed of this fantastic place... It is the best place to stay if you want to visit Oia and keep...
    Reviewed 1 October 2014
    Nice house with a big terrace. Off the beaten track but only a few minutes from the bus-stop. Beautiful view to the aegean sea and the sunset ;-)Very cooperative landlady
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    About this property
    The Sunny Winehouse, (Studio apartment on the terrace): This is a small house built in the traditional Santorinial way, on the top of an old winery (“Winery house”). Although connected to the winery's court via step stone stairs, this house has an independent entrance from the pedestrian road. In...
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    84702, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Wineryhouse and 2 guest houses1 / 64
    (10)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Ocean Views
    • Terrace
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2017
    A group of 10 persons including 4 children decided a reunion in Santorini. As I am familiar with the island chose to rent a house in Finikia, so we could be away from the...
    Reviewed 8 August 2016
    This is property is well off the beaten track, and so is a bit if a hike down narrow pathways from the main road with heavy suitcases, however it is well worth it when you get...
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    About this property
    The main house and each one of the 2 independent guesthouses can be rented all together (for families or groups of friends), but also as individual units. This Old winery building complex, is restored to a luxury villa, consisting on 3 houses. It is located on the north-west side of Santorini, at...
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    84702, Oia, Santorini
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Oia Waves Cavehouses complex, caldera view, low winter rates1 / 62
    (41)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Ocean Views
    • Grill
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    We so enjoyed our time here. The house is comfortable and quiet. The view and setting are absolutely stunning. Sea breezes, birds calling, music from the boats below are...
    Reviewed 19 January 2018
    Dear Anastasya and Maria, thank you from all our hearts for this best vacation! Your cave house is the best place in all Santorini !!! It’s romantic place with unbelievable...
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    About this property
    Our house called Oia Waves, is an old traditional cave house of Oia, Santorini, built on the Caldera cliff with a spectacular view of the volcano and Thirassia island in the center of Oia village, just below the picturesque two blue domes. It consists of three units. All the units have the same...
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    Location Information
    84702, Oia, Santorini
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lava Cave with outdoor Hot Tub and Panoramic View1 / 17
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    • Wi-Fi
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2017
    It's only short walk from the most famous dome in Oia , lava cave house is not very big but it's nicely designed . It's very user friendly and comfortable . The jacauzzi was...
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    About this property
    Live the myth by staying in a cave that used to be a sailor's domicile back in 1875. Today after a full restoration, it has been turned into a jewel, keeping its traditional cave-curved Aegean island style with its pearl white walls. Lava Cave used to be a sailor's domicile back in 1875. The...
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    Location Information
    84702, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    The Sunny Winehouse1 / 38
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2015
    We spent an entire week in the Sunset house and had the time of our lives. The place was very clean, cozy, quiet and with a romantic view of the sunset. It's also a 10 minute...
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    About this property
    The 'Sunny Winehouse' (Studio apartment on the terrace): This is a small studio, (38 sq.m), built in the traditional Santorinian way, on the top of an old winery (“Winery house”). Although connected to the winery's court via step stone stairs, this studio is completely independent and has his own...
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    Location Information
    847 02, Oia, Santorini
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    House of the singing birds1 / 37
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Garden
    • Ocean Views
    • Wi-Fi
    • Grill
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2016
    We have just returned from a week at the house iof the singing birds., lovely accommodation and would definitely recommend it.Georgina is very knowledgeable on the area and gave...
    Reviewed 12 October 2015
    We had such an enjoyable stay at the 'singing birds' . The location was a haven of tranquility and Finikia, a delightful traditional settlement, was lovely to retreat to after...
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    About this property
    The House of the Birds (Guest house on the oriental garden)part of the "Winery Villa" complex: This small house is and Independent Studio of 30 sq. m. in three levels. It is including bedroom with “antique” style double bed, sizable bathroom, kitchenette with separate entrance, and private terrace...
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    84702, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Als Mansion for a memorable stay in Oia Santorini!1 / 36
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Private Garden
    • Housekeeping Included
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2016
    what i loved best, the great hospitality, the amazing sheets and the luxury decoration. I adored the little terrace from where i could see the breathtaking sunset and the two...
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    About this property
    Als Mansion (inspired by the word Als meaning “sea” in ancient Greek) is an extravagant captain’s house built with the traditional Oian architecture that gives out an authentic 18th century sense of Santorini! This is a totally private villa that can accommodate up to 7 people. The courtyard and...
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    847 02, Oia, Santorini
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Oia's nest1 / 20
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • Terrace
    • Balcony
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2017
    Oia's Nest is perfect! We could not have picked a better place to stay in all of Oia. The home itself is simply lovely --- it is decorated superbly, it is very comfortable and...
    Reviewed 8 August 2015
    We stayed in the nest house for a week in June. We couldn't have asked for a more wonderful experience. The setting was beautiful, the house was peaceful and hidden away from...
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    About this property
    Oia ,is the most famous village of Santorini. Practically a vertical village on the edge of caldera with amazing view. Except the main street linking with the capital village of Fira, are no streets but only narrow paths between the labyrinth of white houses most of them curved inside volcano's...
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    84702, Oia, Santorini
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Alafouzou Cave Loft1 / 26
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Ocean Views
    • DVD Player
    • Housekeeping Included
    • Hot Tub
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2018
    We along with our teenage boys stayed here for almost a week in July 2017. From reservation to the end of our trip, Sofia was excellent and arranged everything for us - luggage...
    Reviewed 19 June 2017
    This wonderful home was exactly what we wanted for our week stay in Oia. The host was great about picking us up at the airport, porters to handle the bags, stocking the...
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    About this property
    We invite you to spend your holidays in our luxurious villa, on an out of this world scene, in Santorini island.The villa is located in the center of the old part of Oia right next to the spot which is well known worldwide for the sunset. It is an area where you can enjoy your dinner at the...
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    84702, Oia, Santorini
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Architect's house1 / 84
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Waterfront
    • Housekeeping Included
    • Ocean Views
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2015
    The best view in the world. Excellent house and service. I'm happy because I have a chance to visit this house.
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    About this property
    Renowned as Santorini's most celebrated villa, the Architect's House is truly one-of-a-kind! Just minutes away from the vibrant town of Fira, yet worlds apart, this dazzling villa blends the ultimate architectural style and mesmerizing interior design with the eternal exquisite beauty of Santorini!...
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    847 02, Oia, Santorini
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    The Diamond Rock Venue - Weddings1 / 42
    (33)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Waterfront
    • Ocean Views
    • Air Conditioning
    • Hot Tub
    • Housekeeping Included
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We reached out to The Diamond Rock wedding planners about a year and a half before our planned wedding date. Seems like there are a million wedding planners in Santorini, but...
    Reviewed 2 weeks ago
    - Amazing venue & location- Amazing service- Amazing communication- Amazing people - Amazing Organization- Amazing supportAll in all just an amazing experience. We...
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    About this property
    Live your dream wedding at the Diamond Rock Venue, with panoramic views of the mysterious caldera, the stunning volcano and the magnificent blue of the Aegean Sea, feeling the vibrant energy and distinctive character of Santorini. Diamond Rock Venue can accommodate up to 100 guests for ceremony...
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    Location Information
    84700, Oia, Santorini
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Private Garden
    • Wi-Fi
    • Balcony
    • Grill
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Red Winehouse is one individual house: This was one of the last wineries which operated in Finikia village. The winery belonged to a rich family, and it is one exceptional building including a huge canava (domed wine factory) and residential chambers. This impressive construction was built by...
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    84702, Oia, Santorini
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Shared Garden
    • Balcony
    • Terrace
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The House of the Birds (Guest house on the oriental garden) part of the 'Winery Villa' complex: This small house is and Independent Studio of 30 sq. m. in three levels. It is including bedroom with “antique” style double bed, sizable bathroom, kitchenette with separate entrance, and private...
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    847 02, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Housekeeping Included
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ODE is the name of Lyric Poetry, by the ancient Greeks. This poetry was giving praise and was glorifying great events at those days, like Pindar, the ancient poet, did. He wrote the Ode to the Winners of the Olympic Games. Much later, the German poet Friedrich Schiller wrote the Ode to Joy (an die...
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    84702, Oia, Santorini
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Winery Villa1 / 46
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Outdoor Dining Area
    • Terrace
    • Grill
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2015
    It was our first time in Santorini, for us and our friends as well. Island was busy and noisy, crowded with tourists. We got scared about our holiday, as we intended to relax...
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    About this property
    Traditional restored winery consisting of two separate houses with private oriental garden and tiny swimming pool in Finikia (Oia - Santorini). Offers privacy,relax, ocean and sunset view from the terraces Old wine factory complex (Canavas), probably since the middle ages, took its final form in...
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    847 02, Oia, Santorini
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blessed by the Gods, Santorini is a divine place that exceeds its worldwide reputation. Light, water, volcanic rock, 'infinite blue'... Nature is magnificent, yet within human measure. Its magic is immense, it's eternal beauty, engaging. Villa Anthimos' terrace: Wow! A frameless window to the...
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    847 02, Oia, Santorini
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Being at the premises of an award winning multi-suite property that reflects the traditional Aegean architecture and overlooking the island’s volcanic crater or caldera, the Lopoulos represents the most luxurious, dreamy escape in a Mediterranean setting beyond compare. Located on the cliff edge of...
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    847 02, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Waterfront
    • Wi-Fi
    • Housekeeping Included
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    84702, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blessed by the Gods, Santorini is a divine place that exceeds its worldwide reputation. Light, water, volcanic rock, 'infinite blue'... Nature is magnificent, yet within human measure. Its magic is immense, it's eternal beauty, engaging. Oia Mansion, the exclusive Sea-Captain's luxury villa,...
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    Location Information
    84700, Oia, Santorini
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Being at the premises of an award winning multi-suite property that reflects the traditional Aegean architecture and overlooking the island’s volcanic crater or caldera, the Dimitriades represents the most luxurious, dreamy escape in a Mediterranean setting beyond compare. Located on the cliff edge...
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    Location Information
    847 02, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Outdoor Dining Area
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Grill
    • Ocean Views
    • Terrace
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The main house and each one of the 2 independent guesthouses can be rented all together (for families or groups of friends), but also as individual units. This Old winery building complex, is restored to a luxury villa, consisting on 3 houses. It is located on the north-west side of Santorini, at...
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    Location Information
    847 02, Oia, Santorini
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Ilivatos  Oia  .. The house of your private escape1 / 75
    (26)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Balcony
    • DVD Player
    • Grill
    • Ocean Views
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2017
    My husband and my family stayed at Ilivatos in late September. We chose these beautiful villas for its perfect setting for a wedding! After reading reviews, I knew that this was...
    Reviewed 12 July 2017
    Stunning. The pictures don't do it justice. Ilivatos is the perfect way to visit Oia. In fact, if you google image Oia, most images include shots of Ilivatos. Our group of 6...
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    About this property
    Ilivatos is a traditional Cycladic Santorinian house , situated in the heart of Oia ..Santorini's best Sunset point. Ilivatos is a 4 bedroom villa lying on 3 ground levels ... The panoramic views of the volcano, the neighboring volcanic islets and the legendary sunsets form an experience beyond...
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    Location Information
    87202, Oia, Santorini
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Cave House Oia Caldera1 / 31
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    84700, Oia, Santorini
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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