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Pet Friendly Holiday Rentals in Oia

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    Travellers to Oia are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    25 Matching Rentals in OiaView all 163 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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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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
    Wineryhouse where dreams live......1 / 48
    (20)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 19 August 2019
    You will not be disappointed if you choose to stay here in Finikia. The ‘village’ is quaint, and it will take some time for you to find your way around the maze of little...
    Reviewed 23 July 2019
    Everything we wanted in our stay in Santorini was not only matched but exceeded. The customer service we received from the second we booked to when we left was friendly, helpful...
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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
    By the Mill, Caldera, Oia - private, spacious, sunset and volcano views1 / 31
    (4)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 23 May 2019
    Stayed 5 nights at this beautiful villa with views to die for overlooking the caldera. The villa had 3 bedrooms with 3 bathrooms, more than adequate space for 3 of us. It was...
    Reviewed 29 March 2019
    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...
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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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    The sunset windmill1 / 40
    (11)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 23 October 2019
    We had a larger group so it was hard to find a place for us all to stay in Oía, but this place fit us all very comfortably and even had multiple bathrooms which was great!! It...
    Reviewed 5 August 2019
    Staying in the Sunset Windmill was one of our favorite Places in Oia so far. What a unique structure and location. The wind blown cliffs of the top of the island create a...
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    About this property
    A traditional Aegean island windmill has been transformed into a fully equipped 69 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
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Terrace
    • Private Garden
    • Ocean Views
    • Grill
    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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    Oia, Santorini 84702
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    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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    Oia, Santorini 847 02
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • Terrace
    • Grill
    • Balcony
    • Wi-Fi
    • Shared Garden
    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 terrace...
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    Oia, Santorini 84702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Oia, Santorini 84702
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    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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    Oia, Santorini 847 02
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    The Diamond Rock Venue - Weddings1 / 65
    (41)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 12 January 2020
    The team at Diamond Rock is absolutely incredible. My now husband and I planned our wedding on Santorini with them from the U.S. and could not be happier with how our day turned...
    Reviewed 14 August 2019
    I got married here in July this year - amazing!!! The place is just out of this world, more then the photos you see online. We did everything via the internet; reviews, messages...
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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
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    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
    Oia, Santorini 847 02
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Ftelari Villa1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Grill
    • Private Outdoor Pool (Heated)
    • Balcony
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 February 2020
    We had an unforgettable week here, relaxing and enjoying every single day! The most amazing panoramic view of the Caldera !!!I just booked my 2020 stay …
    Reviewed 22 August 2019
    Ftelari Villa is an oasis. It has the best view in Santorini of the Caldera, the volcano, Akritori, and Thirasia. I had the absolute best time there. It was peaceful and I felt...
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    About this property
    Celebrated as Santorini’s most renowned hideaway, the Ftelari Villa is a well-kept secret amongst those who seek the true luxury of peace and elegance in an environment of unprecedented natural beauty. Designed with love and respect to local tradition and constructed with contemporary materials,...
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    Oia, Santorini 84700
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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...
    View all property information
    Location Information
    Oia, Santorini 847 02
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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
    Pina Caldera Residence1 / 32
    (2)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 18 June 2019
    If you are reading this review and thinking of booking here - do it!We have had an amazing 3 days away. The accommodation is set in a traditional cave house, simple but clean...
    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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    Unique Restored 1868 Wine Canava - Caldera View, Private Pool, Sunbathing Deck1 / 22
    (43)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • 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 22 September 2019
    This property excels in every way! Five couples were accommodated on this property properly with private baths and comfortable beds. Grand Canava is excellently located in...
    Reviewed 7 August 2019
    Our family just spent 11 days at Grand Canada. The property is beautiful, the location perfect and every direction you look in is a postcard. Roxanne is a wonderful, helpful...
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    About this property
    Grand Canava is offered as an entire residence and it has been built to comfortably accommodate 12 people. It is ideal for families and friends travelling together and children of all ages are welcome. An inviting 7 meter long pool is situated at the centre of the courtyard, wide enough for a...
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    Oia, Santorini 847 02
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    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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