Best OverallImerovigli · All Plunge Pool Rooms · Largest Infinity Pool on Caldera
Imerovigli's most critically acclaimed hotel — the largest infinity pool on the caldera edge, 180° panoramas centered on Skaros Rock, and Chef Lefteris Lazarou's Varoulko Santorini. Twenty rooms and suites, all with private heated plunge pools; champagne breakfast served daily with caldera views.
Largest Infinity Pool Caldera20 Rooms All Plunge PoolsVaroulko Michelin Dining180 Degree PanoramaChampagne Breakfast
From $700 / night
Best ViewsOia · 30 Suites with Heated Plunge Pools · Three Infinity Pools · Botrini's Restaurant
Oia's gold standard — 30 cliffside suites, each with a private heated plunge pool overlooking the caldera, plus three infinity pools and Michelin-caliber Cycladic cuisine at Botrini's. Rare elevator access and a centuries-old wine cellar.
Gold Standard Oia Hotel30 Suites All Heated Plunge PoolsThree Infinity PoolsBotrini's RestaurantRare Elevator Access
From $800 / night
Best LuxuryOia · Cave Suites in Volcanic Cliff · Elevator · Petra Restaurant · Private Pools & Jacuzzis · From ~€600
The most architecturally authentic cave hotel in Oia — Canaves Oia Suites, hand-carved into the volcanic cliff with curved white walls, vaulted ceilings, and private plunge pools. One of the very few luxury caldera properties with an elevator. The Petra restaurant serves Mediterranean cuisine on a terrace with full caldera views. Famous celebrity guests include Jennifer Lawrence and Helen Hunt. Five Canaves properties on the island offer different experiences — this is the flagship. From ~€600.
Cave Carved Volcanic CliffElevator Access RarePetra Restaurant Caldera ViewJennifer Lawrence GuestPrivate Pools Jacuzzis
From ~€600 / night
Best DesignLuxury · Boutique · Adults-Oriented · Caldera Views · Romantic · Design Hotel
The most architecturally distinctive hotel in Santorini — Perivolas, a collection of cave houses carved into the cliff with minimalist white interiors and one of the most iconic infinity pools on the island. Quiet location just outside central Oia. Strong wellness focus with spa and private terraces.
From ~€600
Luxury · Caldera Views · Honeymoon · Resort-Style · Design · Five-Star
A more understated, design-forward alternative to Oia’s whitewashed hotels — Mystique blends into the cliff with organic materials, earthy tones, and exceptional privacy. Known for its wine cave, curated dining, and romantic atmosphere.
From ~€700
Ultra-Boutique · Romantic · Design · Quiet Location · Caldera Views · Hidden Gem
One of the most intimate hotels on the island — The Vasilicos, a former private residence turned boutique property with just a handful of suites. Feels like staying in a beautifully designed home, with exceptional sunset views and highly personalized service.
From ~€500
Luxury · Caldera Views · Honeymoon · Central Location · Boutique · Five-Star
One of the original luxury cave hotels in Oia — Andronis Boutique Hotel sits directly in the center of the village with classic caldera views, private plunge pools, and Lauda, one of the island’s most historic restaurants.
From ~€600
Luxury · Modern Design · Quiet Location · Sunset Views · Suites · New Hotel
A newer, more spacious alternative to traditional cave hotels — Santo Mine offers large terrace-style suites with private pools and unobstructed sunset views, slightly removed from the busiest part of Oia.
From ~€500