Waterfront vacation rentals in Oia

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Top-rated waterfront rentals in Oia

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Guest favorite

Cycladic home in Oia Santorini Cyclades

4.93 out of 5 average rating, 149 reviews

SantoriniParadise: HELIOS cave house, sunset view!

HELIOS Cave house is a spacey, well-lit home. In the heart of old Oia, it offers unobstructed view of Santorini's famous sunsets. 'SISTERHOOD of the traveling pants' was filmed just there! HELIOS private terrace is on top the cave house and it is exclusive for HELIOS guests. Jacuzzi for 3 persons is available on Tuesday, Thursday & Saturday, just 2 minutes away. Breakfast provisions: honey, butter, marmalade, sugar, milk, cereal, bread, cheese, ham, fruits, yoghurt, tea and 3 kinds of coffee.

Aug 23 – 30

G$121,511 GYD per night

Guest favorite

Cave in Red beach

4.96 out of 5 average rating, 103 reviews

Cueva del Pescador

Enjoy two luxurious, newly-remodeled cave dwellings only two meters from the sea: Cueva de olas and Cueva del pescador! These gorgeous spaces are perfect for discerning honeymooners, couples, or anyone who wants to take a break from the real world -- and from the typical tourist traffic of Santorini. Cueva de olas was originally the residence of a local fisherman; Cueva del pescador was his boat-house. Traditional decor and outstanding hospitably complete this perfect, unique rentals!

Aug 7 – 14

G$73,135 GYD per night

Guest favorite

Cycladic home in Akrotiri

5.0 out of 5 average rating, 145 reviews

Akrorama - Anemos , private pool

Anemos suite is located in Akrotiri overlooking the caldera and the volcanic islands . It is a suite with Private, Infinity heated Cave style plunge pool with Jet system and private patio. There is a king size bed that can accommodate two person. Daily breakfast is included and served in your suite . There is a cleaning service included. Inform us about your arrival details in advance , we can arrange a taxi/transfer for you. Renovated interior 2024 photos coming soon!

Oct 3 – 10

G$64,919 GYD per night

Superhost

Cycladic home in Monolithos

4.93 out of 5 average rating, 115 reviews

Sea & Sky Luxury Beach House

This elegant and comfortable, newly renovated studio in the traditional Cycladic style, is located right by the beach of Agia Paraskevi. In a quiet area, away from the crowds and noise, it makes a perfect location for those who wish to have a relaxed and private vacation. While offering the advantage of tranquillity, the studio is also only 10-15 minutes on foot from the Kamari area which features a multitude of restaurants, coffee shops as well as other stores.

Oct 12 – 19

G$29,889 GYD per night

Guest favorite

Cycladic home in Imerovigli

4.94 out of 5 average rating, 223 reviews

Chess House-Traditional Home (Renovated '23)

My place is a traditional Santorini home! Built on the Caldera (Cliff), into the rock, where families of the people of the sea would live, always looking out to the Aegean where their loved ones made their living.. You’ll love my place because of the impeccable view, the peace and quiet, the traditional home experience which is so rare these days.. My place is good for one or two couples or families with or without kids. Reserved parking for guests is included.

Mar 14 – 21

G$137,950 GYD per night

Guest favorite

Cycladic home in Oía

4.95 out of 5 average rating, 199 reviews

Bluedome Suite by Otium Villas & Suites

This is a newly renovated cavehouse that dates back to the 1890's. Situated in one of the most famous neighbourhood's in Oia "Monastiraki" next to the famous St Spyridon Bluedomes. It has been renovated keeping traditional cycladic cavehouse architecture at the forefront of the design while utilising modern building materials. This suite is ideal for couples and families. Its' minimal designed spaces inspire relaxation and comfort for the modern traveller.

Mar 19 – 26

G$73,873 GYD per night

Guest favorite

Apartment in Thira

4.93 out of 5 average rating, 177 reviews

Artemisia Apartment 3

Located in the picturesque village of Imerovigli, Artemisia Apartment offers self-catering accommodation, as well as a spacious furnished terrace with amazing views of the caldera and the volcano. Complimentary Wi-Fi is provided in all areas . Artemisia's apartment features wood furniture, a 26'LCD TV, a small fridge with a freezer , a kettle, and a coffee maker for breakfast and cooking utensils. The bathroom includes free toiletries and a hairdryer.

Mar 22 – 29

G$54,065 GYD per night

Guest favorite

Home in Fira

4.98 out of 5 average rating, 145 reviews

Barocco Bello Studio

Welcome to Barocco Bello Studio The house is at Firostefani which means the "Crown of Fira". This area is one of the highest points on the Caldera giving it a unobstructed and magnificent view of the sea, the volcano and most of Santorini. The main city center Fira is a ten-minute walk along one of the most scenic roads of the island. Although a traditional house it contains the most modern amenities , and the interior design has a pop Baroque flavor

Oct 8 – 15

G$45,508 GYD per night

Guest favorite

Cycladic home in Oia

4.83 out of 5 average rating, 225 reviews

Big Blue villa with Hot Tub and Sea View in Oia

Discover unparalleled luxury at our villa in Oia, Santorini. With breathtaking views of the caldera and impeccable design, our spacious accommodations offer a perfect blend of comfort and elegance. Enjoy a private hot tub, attentive hospitality from our dedicated staff, and the convenience of being located in the heart of Oia. Experience the epitome of relaxation and indulgence in this stunning retreat.

Nov 15 – 22

G$94,521 GYD per night

Guest favorite

Cycladic home in Οία, Σαντορίνη

4.9 out of 5 average rating, 141 reviews

Michelangelo Beach Villa with Sea View

Michelangelo Beach Villa is a perfect getaway destination for those seeking contact with nature and peace of mind. The villa is decorated in respect to the island's tradition, in pastel colors so our guests can take in as much of nature's and sea's beauty as they can. The fresh water hydromassage is not operating during December, January and February.

Sep 6 – 13

G$89,320 GYD per night

Guest favorite

Villa in Imerovigli

4.99 out of 5 average rating, 157 reviews

Villa Aronia

This immaculate, 80 m^2 and fully equipped Villa invites comfort and tranquility. Highlights include breathtaking view, secluded beach, only 20 meters away, spacious garden setting for relaxing and entertaining and private parking. Perfect for anyone, this home is ideally positioned to enjoy all year round in Santorini.

Nov 29 – Dec 6

G$74,814 GYD per night

Guest favorite

Apartment in Imerovigli

4.86 out of 5 average rating, 102 reviews

Olia Dome, 2 bedrooms, 2 jacuzzis and volcano view

Olia Dome is part of Olia villas & suites, a brand new property that opened in 2019. Located in Imerovigli and at the highest point of the caldera, offering a breathtaking view of the caldera and the volcano. The indoor areas of the Dome are 70 sqm and the outdoor areas are 85 sqm

Oct 7 – 14

G$104,740 GYD per night