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Search results; Over 1,000 homes

Top guest favorite
Sea views from 4 terraces greet you at this 15th-century Emporio castle
1 bedroom, 2 beds, 1 bath
Aug 13 – 18
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4.95 out of 5 average rating, 56 reviews
Guest favorite
Stone walls and a rock-carved bedroom greet you at this Fira dome villa
4.92 out of 5 average rating, 310 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 3 – 8
Top guest favorite
Private room
Soak in caldera views from your private balcony at this Oia dome suite
4.99 out of 5 average rating, 157 reviews, 1 bedroom, 1 bed, 1 bath
Nov 4 – 9
Top guest favorite
This cave suite in Oia puts you between the blue domes with caldera views
4.99 out of 5 average rating, 229 reviews, 1 bedroom, 2 beds, 1 bath
Nov 26 – Dec 1
Top guest favorite
Soak in caldera views from your heated jacuzzi at this Oia Cycladic house
5.0 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 2 baths
Nov 8 – 13
Top guest favorite
This Santorini cave house gives you caldera and blue dome views from a private pool
4.95 out of 5 average rating, 408 reviews, 2 bedrooms, 3 beds, 2 baths
Oct 24 – 29
Top guest favorite
Sea views from your balcony at this top-floor Fira house with Cycladic charm
4.98 out of 5 average rating, 142 reviews, 3 bedrooms, 3 beds, 1 bath
Aug 24 – 29
Guest favorite
This 1901 cave house carved into volcanic rock gives you a jacuzzi in Megalochori
4.93 out of 5 average rating, 178 reviews, 3 bedrooms, 3 beds, 3 baths
Oct 1 – 6
Top guest favorite
Soak in Aegean views from your private hot tub at this Caldera cliff villa
4.94 out of 5 average rating, 210 reviews, 2 bedrooms, 5 beds, 3 baths
Oct 13 – 18
Guest favorite
Caldera views greet you from the private pool at this Oia cave house
4.97 out of 5 average rating, 310 reviews, 2 bedrooms, 4 beds, 3 baths
Oct 13 – 18
Top guest favorite
This 1920s cave villa in Imerovigli gives you caldera views and a heated plunge pool
4.99 out of 5 average rating, 173 reviews, 2 bedrooms, 2 beds, 2 baths
Sep 3 – 8
Top guest favorite
This Santorini villa gives you a private pool amid vineyards and sea views
4.98 out of 5 average rating, 101 reviews, 4 bedrooms, 5 beds, 3.5 baths
Sep 9 – 14
Top guest favorite
Caldera and volcano views greet you at this Santorini cave house with a private pool
4.95 out of 5 average rating, 80 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 21 – 26
Guest favorite
Take in Caldera sunsets from your private pool at this Pyrgos villa
4.96 out of 5 average rating, 201 reviews, 2 bedrooms, 2 beds, 2 baths
Sep 18 – 23
Top guest favorite
This beachfront Oia villa puts you on the caldera with a seafront terrace
4.94 out of 5 average rating, 145 reviews, 4 bedrooms, 4 beds, 3 baths
Aug 22 – 27
Top guest favorite
This brand-new Fira Cycladic house puts you 2 minutes from the main square
4.98 out of 5 average rating, 210 reviews, 1 bedroom, 3 beds, 1 bath
Sep 28 – Oct 3
Top guest favorite
Soak in Caldera views from your private pool at this restored Oia cave
4.95 out of 5 average rating, 263 reviews, 1 bedroom, 1 bed, 1 bath
Oct 17 – 22
Top guest favorite
Look out over the caldera from your heated infinity pool at this Imerovigli villa
5.0 out of 5 average rating, 71 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 21 – 26
Top guest favorite
Soak in 2 heated jacuzzis at this traditional Megalochori cave house
4.98 out of 5 average rating, 103 reviews, 4 bedrooms, 6 beds, 5 baths
Sep 15 – 20