Villa holiday rentals in Santorini caldera

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Top-rated villa rentals in Santorini caldera

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Top guest favourite

Villa in Santorini

4.98 out of 5 average rating, 121 reviews

SPECTACULAR SANTORINI VILLA-CAR RENTAL INCLUDED

Description: Mansion Kyani is a secluded Hillside villa in Santorini's prettiest village. It offers three self-contained apartments spread over two spacious floors, a sunny terrace providing great views, and a huge yard with private pool & copious lounging spots. -A manual 5seater Car Rental (Fiat Panda or similar) is offered complimentary for the duration of your stay. This does NOT apply for special offers and not guaranteed for last minute reservations (depends upon agent's availability).

Top guest favourite

Villa in Pyrgos Kallistis

4.99 out of 5 average rating, 114 reviews

Santorini Sky | Panoramic Villa *NEW*

SPECIAL 2025 RATES. BOOK NOW! As seen in Vanity Fair, Conde Nast Traveller and Architectural Digest, this amazing villa will take your breath away. With panoramic windows in every room, a large private terrace with infinity pool, and a separate heated jacuzzi, you can enjoy incredible sea views from sunrise to spectacular sunset. This is paradise! Includes complimentary access to our Sky Lounge, with breakfast pantry items and snacks throughout the day. Contact us today with any questions!

Top guest favourite

Villa in Fira

4.97 out of 5 average rating, 168 reviews

Ambeli Luxury Villa|Private Pool |HotTub&Breakfast

Ambeli Villa is situated in the region of Megalochori, with a total living space of 530sq.m. A newly anti-seismic constructed building covering all the official guidelines to maximize the security of our guests offers four gracious bedrooms and 4 bathrooms, which can accommodate up to 9 guests. The swimming pool and the outdoor heated Jacuzzi will offer you a sense of relaxation and wellness. "Homemade breakfast" and daily housekeeping are included at the price

Guest favourite

Villa in Pyrgos Kallistis

4.94 out of 5 average rating, 100 reviews

White Orchid Villa | Private Pool | Sunset View

Nestled in the charming village of Pyrgos Kallistis, the heart of Santorini, White Orchid Villa offers breathtaking panoramic views of the Caldera, Fira, Oia, and the Aegean Sea. Blending Cycladic architecture with modern design, the villa promises luxury, privacy, and comfort. With warm Greek hospitality and exceptional amenities, your stay at White Orchid Villa will be truly unforgettable.

Guest favourite

Villa in Fira

4.98 out of 5 average rating, 139 reviews

Calderas Hug 1 (Panoramic Sea View& Prive Hot Tub)

Calderas Hug 1 is a suite perfectly situated in the famous Caldera, offering an astonishing direct sea view to the infinity azure of the Aegean sea! Our property, is beautifully settled in the volcanic surface of Caldera cliff, following the traditional Cycladic white-washed architectural principals, providing our Guests a sense of serenity and a plethora of luxury amenities.

Guest favourite

Villa in Vourvoulos

4.88 out of 5 average rating, 127 reviews

NEW La Estrella - Levantis Suite & Private Jacuzzi

La Estrella - Levantis Suite (55 sq.m.) is beautiful situated in Vourvoulos village, just 600m away from the famous Imerovigli town, offering a direct stunning sea view to the Aegean. The property combines the famous traditional Cycladic white-washed architecture with the modern mindset, being able to provide our guests all the luxurious amenities.

Superhost

Villa in Fira

4.73 out of 5 average rating, 107 reviews

180° Caldera by Stylish Stays

“180° Caldera” is located at the renowned Firostefani area of Santorini and has a panoramic, 180° view of the sought after volcanic caldera of the island. The Villa is built in the traditional local style with the iconic amphitheatric Santorinian fashion, which gives the impression of a balcony hanging over the Caldera and the Aegean Sea.

Guest favourite

Villa in Akrotiri

4.95 out of 5 average rating, 122 reviews

Serra Exclusive Suites

Our newly-built suites are providing a modern and luxury setting with the best view of the entire Caldera of Santorini (the cliffs, the volcano, Oia, Fira, etc.) where our guests will be pampered and feel like home thanks to the famous Greek hospitality. You can explore an unparalleled travel experience you would not miss for the world.

Top guest favourite

Villa in Oia

5 out of 5 average rating, 142 reviews

Loukia House

Loukia House is a traditional Cycladic cave house carved inside the Oia cliff. The beautiful arched ceilings stretch along the indoor and outdoor space. Its unique location offers panoramic views of the whole island and the caldera. A relaxing terrace gives a sense of privacy in the most sought-after spot in Santorini.