Waterfront vacation rentals in Santorini

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Top-rated waterfront accommodations in Santorini

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Guest favourite

Cycladic homes in Oia Santorini Cyclades

4.93 out of 5 average rating, 150 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.

Nov. 9 – 16

$330 CAD per night

Guest favourite

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!

Jul. 13 – 20

$389 CAD per night

Superhost

Cycladic homes in Imerovigli

4.93 out of 5 average rating, 282 reviews

Pura Vida Cave House

When we acquired the Pura Vida Cave House it was a deserted Gem.. We immediately fell in love with the spot, on the top of a 300 meter cliff - nothing to block your sight but the end of the horizon. We put together a team to reconstruct it entirely, keeping the initial design of the house and blending it with modern touches and technology. The result is a Cycladic beauty, built into the rock, white as can be, to host a couple or a small family, in a fun and elegant environment!

Dec. 23 – 30

$424 CAD per night

Guest favourite

Cycladic homes in Akrotiri

5.0 out of 5 average rating, 146 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!

Sep. 9 – 16

$618 CAD per night

Superhost

Cycladic homes 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

$198 CAD per night

Guest favourite

Cycladic homes 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. 23 – 30

$485 CAD per night

Guest favourite

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. 25 – Nov. 1

$297 CAD per night

Guest favourite

Apartment in Thira

4.93 out of 5 average rating, 177 reviews

Artemisia Apartment 3

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

Mar. 20 – 27

$360 CAD per night

Guest favourite

Cycladic homes in Oia

4.92 out of 5 average rating, 133 reviews

3 Caves suite with Hot-Tub and Caldera View in Oia

Discover tranquility in the heart of Oia at 3 Caves Villa. This luxurious suite seamlessly blends traditional cave-home charm with modern comforts. With a private terrace boasting a bubbling hot tub and panoramic views of the sea, volcano, and caldera, relaxation is inevitable. Explore Oia's treasures within easy reach, then retreat to your cozy bedroom and sleek bathroom for a restful night. Welcome to your unforgettable Santorini escape.

Oct. 22 – 29

$725 CAD per night

Guest favourite

Apartment in Kamari

4.99 out of 5 average rating, 135 reviews

Kalipso Beach House

Peaceful quiet, imaginary sea view and family hospitality are the three main words that can describe my place. Kalipso house is located in a unique spot and it is conveniently located near restaurants, supermarkets, bus station and other facilities. The house is recently renovated and accessible through a traditional path. Just 2 minutes away (walking distance) is the lovely black beach of Kamari with crystal clear waters.

Nov. 7 – 14

$213 CAD per night

Guest favourite

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.

Dec. 21 – 28

$492 CAD per night

Guest favourite

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. 6 – 13

$697 CAD per night