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Oia Smoking Friendly Vacation Rentals

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    Travelers to Oia are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    20 Matching Rentals in OiaView all 162 rentals
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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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    Wineryhouse where dreams live......1 / 48
    (18)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Ilivatos  Oia  .. The house of your private escape1 / 76
    (26)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    By the Mill, Caldera, Oia - private, spacious, sunset and volcano views1 / 31
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Terrace
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Absolutely one of the most spectacular places we have ever stayed - and probably the best place to watch the famous Santorini sunset. Judy’s place is huge - and easily...
    Reviewed September 1, 2018
    Villa By the Mill, Oia exceeded all expectations. First, Judith was amazing. She was prompt in returning VRBO messages, was available during our stay, and all of her...
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    About this property
    100 sq meters of traditional cave house - 3 bedrooms and 3 bathrooms, spread over 3 levels of 100 square meters of private terraces. At Oia's heart - incredible volcano,caldera & sunset views, easy access, and remarkable privacy - just breathtaking! The traditional cave home style of the villa is...
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    Oia, Santorini 84702
    Rental Home - 3 Bedrooms, 3 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 Yard
    • Ocean Views
    • Wi-Fi
    • Grill
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 16, 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 October 12, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ninetta's house1 / 16
    (11)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Ocean Views
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 15, 2018
    Ninetta’s house was absolutely perfect for my 4 days in Santorini. It’s right off the main path making it very convenient to get to, but down enough steps (around 100) that it...
    Reviewed May 30, 2017
    The location of this house is just amazing and the view you have is just wonderful, i loved waking up every morning and looking out to the sea and sitting on the patio having my...
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    About this property
    This is the nest of eagles. A cave house, built on cliffs of the caldera, one of the last houses down from suspended village of Oia. Detached house with private terrace, isolated from tourists crowds above (100 STAIRS), at the absolute tranquility, may become the nest dream for the summer...
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    Oia, Santorini 84702
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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 Yard
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 18, 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 August 8, 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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    Location Information
    Oia, Santorini 84702
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Poseidon Mansion in Santorini1 / 35
    (11)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Patio
    • Air Conditioning
    • Hot Tub
    • Ocean Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 3, 2018
    Myself and two friends went for a girls holiday in Santorini. We had an absolutely wonderful time. The Poseidon mansion is spectacular.Each room is beautiful. The decor is...
    Reviewed October 14, 2018
    My brother booked the home. It was absolutely phenomenal!! I work for a major airline and we travel together often as my husband doesn't care to. We've visited several...
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    About this property
    Poseidon Mansion occupies a privileged location in Santorini. It is a cultural heritage building known from the old years as Captain's house and dates back to 1890.Poseidon Mansion is nestled on the famous cliffs of Oia in Santorini, gazing the beauty of the infinity Aegean Sea and worldwide famous...
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    Location Information
    Oia, Santorini 847 02
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Terrace
    • Private Yard
    • 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Alafouzou Cave Loft1 / 26
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Balcony
    • Ocean Views
    • DVD Player
    • Housekeeping Included
    • Hot Tub
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 6, 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 June 19, 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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    Location Information
    Oia, Santorini 84702
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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 Yard
    • Housekeeping Included
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 25, 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 June 21, 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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Sunny Winehouse1 / 38
    (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 August 27, 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 October 1, 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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    Location Information
    Oia, Santorini 84702
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 November 18, 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 November 18, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Oia Waves Cavehouses complex, caldera view, low winter rates1 / 31
    (43)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Ocean Views
    • Grill
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2018
    Ana and her daughter were the most wonderful of hosts. they made us feel so welcome and at home. The lace is perfect and the view, spectacular. You can enjoy shooting stars and...
    Reviewed July 13, 2018
    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...
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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
    Oia, Santorini 84702
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cave House Oia Caldera1 / 31
    (2)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
    Reviewed September 3, 2018
    If you are going to Oia... this is the place to stay. Truly magical view. It was such a pleasant experience working with Jackie. Outstanding service. From picking us up from the...
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    Location Information
    Oia, Santorini 84700
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Oia's nest1 / 20
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Ocean Views
    • Terrace
    • Balcony
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 4, 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 August 7, 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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    Location Information
    Oia, Santorini 84702
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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...
    View all property information
    Location Information
    Oia, Santorini 847 02
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Housekeeping Included
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Oia, Santorini 84702
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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