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Oia Pet Friendly Holiday Rentals

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    Travellers to Oia are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    23 Matching Rentals in OiaView all 168 rentals
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    Swinging Sunset Villa - Private Pool & Private Spa1 / 53
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    OIA SUNSET VILLAS - villa PEARL -  Pools & Spa1 / 60
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    By the Mill, Caldera, Oia - private, spacious, sunset and volcano views1 / 31
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Wineryhouse where dreams live......1 / 48
    (18)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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 22 September 2018
    Peaceful and beautiful accommodation in Finikia, easy walking distance from the much busier town of Oia. Perfect location for visiting the whole island as local buses to Fira...
    Reviewed 17 July 2018
    We loved our stay at the Wineryhouse-terrific position,plenty of space,very well equipped ,relaxing courtyard,pool.terrace and hammocks under the vines!We were well looked after...
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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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    Oia, Santorini 84702
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    OIA SUNSET VILLAS - villa 'EMERALD' - Pools & Spa1 / 47
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Ocean Views
    • Wi-Fi
    • Housekeeping Included
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 December 2014
    We stay for five days at villa EMERALD. Everything was perfect. The location, was so quiet, away from the crowds, but so close to the village. The sunset view was excellent...
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    About this property
    Villa 'EMERALD' at OIA SUNSET VILLAS is one of six Boutique villas, elegantly decorated. The villa is located in the north of Santorini Island in the traditional settlement of Oia (Ia) village. It is just 400 m. from the village, but so far enough away from “civilization” to be peaceful and the...
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    Oia, Santorini 84702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    The sunset windmill1 / 55
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Ocean Views
    • Balcony
    • Wi-Fi
    • Washer
    • Parking
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2018
    Ok let me start by saying the positives here far outweigh the negatives! First and foremost you are in the very edge of the island and the sunset is beyond words! And you get...
    Reviewed 30 May 2017
    Sunset windmill is in the most perfect location, with a fabulous pool nearby and stunning sunset views. Would most definitely recommend.
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    About this property
    A traditional Aegean island windmill has been transformed into a fully equipped 74 sq. mt. house with modern facilities. The mill has an attic where children love to sleep and a private yard ideal for breakfast or night cocktails with guests. Guests have access to the center of Oia with just 5 min...
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    Oia, Santorini 84702
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    House of the singing birds1 / 37
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Oia, Santorini 84702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Winery Villa1 / 46
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Oia, Santorini 847 02
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Wineryhouse and 2 guest houses1 / 64
    (10)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Oia, Santorini 84702
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Oia, Santorini 84702
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Als Mansion for a memorable stay in Oia Santorini!1 / 36
    (2)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 25 November 2018
    Beautiful house spent with the family for a long weekend.We all loved it so much that we will come back, really pretty decoration, comfy beds, towels and bedding changed.We...
    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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    Location Information
    Oia, Santorini 847 02
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    The Diamond Rock Venue - Weddings1 / 65
    (38)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • 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 19 November 2018
    Words cannot express how thankful my husband and I are for this amazing team! The Diamond Rock has been there for us for two years and helped us plan our magical day, they made...
    Reviewed 18 November 2018
    When George and I decided to have our wedding in the most magical place in the world, Santorini. We knew we had to find the right wedding planners for us to help bring our...
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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
    Oia, Santorini 84700
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Sunny Winehouse1 / 114
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Oia, Santorini 84702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Sunny Winehouse1 / 38
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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
    Oia, Santorini 847 02
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Terrace
    • Secure Parking
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Erifili with jacuzzi, is the ideal place to stay for those wishing to relax in a beautiful and friendly ambience. Only 2000 meters from the world-renowned village of Oia and just a few steps from its beautiful black sandy beach. It is built according to the traditional architecture, combine a...
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    Location Information
    Oia, Santorini 84702
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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
    Oia, Santorini 847 02
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Pina Caldera Residence1 / 32
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • Hot Tub
    • Wi-Fi
    • Balcony
    • Patio
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 October 2018
    We loved staying at Pina Caldera! The pool & patio overlooking the Aegean Sea was spectacular. The house is spacious, clean and very comfortable. The location in Oia was...
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    About this property
    With its breath-taking views over the Oia cliffs, the Pina Caldera Residence is a stunning hideaway for any visitor to the beautiful island of Santorini. The pine tree in the property’s garden is a rare sight on the island and signals exclusivity with characterful charm. This holiday villa is a...
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    Location Information
    Oia, Santorini 84700
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Location Information
    Oia, Santorini 847 02
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anima Residence is a traditional fisherman's house with local architecture and an impeccable view! Enjoy the direct sunset & caldera view from your private balcony. This is a totally private villa that can comfortably accommodate up to 6 guests. It has 3 bedrooms, 1 bathroom and a fully equipped...
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    Location Information
    Oia, Santorini 847 02
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Adrales Cave House1 / 23
    (1)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2018
    Everything perfect except bathroom. 3 bedrooms and only 1 tiny bathroom with awkward tiny shower. Lady caretaker was very nice. Terrace was prime for sunset, though not very...
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    About this property
    Adrales Cave House is a traditional Santorinian cave house featuring a balcony with a direct sunset, sea & caldera view. This is a totally private house that can comfortably accommodate up to 6 guests. It has 3 bedrooms, 1 bathroom and a fully equipped kitchen. Adrales Cave House is just above...
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    Location Information
    Oia, Santorini 847 02
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Unique Restored 1868 Wine Canava - Caldera View, Private Pool, Sunbathing Deck1 / 17
    (39)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Housekeeping Included
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2018
    The villa is in a perfect location, right on the Main Street of Oia. Roxanne is lovely and very helpful with dinner reservations and any questions you have. Rooms were...
    Reviewed 24 July 2017
    In July of 2017, my husband and I rented Grand Canava for a vacation with our three adult sons and two daughters in law. It far exceeded our expectations!! From the moment that...
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    About this property
    Traditional Santorinian residence dating from 1868, newly restored to become one of the most authentic and sought after residences available in Oia, Santorini. Licenced by the Greek National Tourism Organisation (GNTO) with an award that marks the luxury standard in rental accommodation....
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    Oia, Santorini 847 02
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Only 2000 meters from the world-renowned village of Oia and just a few steps from its beautiful black sandy beach. It is the ideal place to stay...
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    Location Information
    Oia, Santorini 84702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Only 2000 meters from the world-renowned village of Oia and just a few steps from its beautiful black sandy beach. It is the ideal place to stay for those wishing to relax in a beautiful and friendly ambience. Villa Alkmini has been built according to the traditional architecture, combine a...
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    Location Information
    Oia, Santorini 84702
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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