Villa vacation rentals in Santorini caldera

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!

An outdoor terrace is shown, featuring a dining table surrounded by light-colored chairs. A private jacuzzi is visible on one side, with panoramic views of the sunset over the sea and distant hills. The space is complemented by sheer drapes and a warm glow from the setting sun.

4.85 out of 5 average rating, 128 reviews

Sunset View Villa Santorini - Outdoor Jacuzzi

Exclusive Luxury Villa with breath-taking PANORAMIC views of the sea, Caldera & Sunset. Upstairs - One of the largest private jacuzzi terraces in Santorini with pergola & kitchen/bar, stunning views and Alfresco dining and lounging. Downstairs - 3 double Bedrooms, 2 bathrooms, lounge/dining room, Modern kitchen, outdoor dining table in the tranquil courtyard. Laundry with washer and drier. Daily clean, linen, towels & toiletries. Personal Manager & concierge services.

The outdoor area features a private swimming pool with crystal-clear water, surrounded by sunbeds and lush landscaping. A shaded lounging area with an airy canopy provides a serene view of the surrounding vineyards, while the warm sunset creates a tranquil ambiance.

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

A sparkling infinity pool reflects the landscape, featuring a stylish ice bucket with a bottle of champagne and two elegant glasses nearby. A decorative plate holds a variety of fresh fruits, providing a vibrant centerpiece against the serene backdrop of the Aegean Sea.

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.

A private terrace features wooden lounge chairs surrounding a hot tub, offering expansive views of the Aegean Sea and the volcanic islands at sunset. The tranquil atmosphere is enhanced by soft, pastel skies reflecting over the water.

4.98 out of 5 average rating, 142 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.

A private Jacuzzi tub is positioned on a balcony, with a stunning view of the Aegean Sea and a sunset reflecting on the water. Soft clouds are visible in the sky, and a rolled towel is neatly placed beside the tub.

4.88 out of 5 average rating, 129 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.

A crystal-clear plunge pool glistens under the sun, surrounded by whitewashed stone walls. Decorative planters add splashes of green, while pink flowers provide a soft contrast. The image captures a backdrop of traditional Santorinian architecture against a bright blue sky.

4.95 out of 5 average rating, 179 reviews

The Painters House

The Painters House is a lovingly restored traditional villa right in the heart of the old town of Fira. Just a few minutes walk from the famous Caldera and the main square, the villa offers luxurious accommodation for adults over 18 in a quiet location whilst providing easy access to the many restaurants and famous nightlife of the capital.

Superhost

A serene outdoor area features a private pool with a smooth edge overlooking the sea. Comfortable sun loungers are positioned nearby, with captivating views of the sunset reflecting on the horizon and the gentle slopes of Santorini in the background.

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.

A private pool is featured within a sunlit terrace, surrounded by modern architectural elements. The clear water of the pool reflects the sky, while lounge chairs are positioned nearby for relaxation. The expansive space allows for unobstructed views of the surroundings.

4.95 out of 5 average rating, 123 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.

Two wooden lounge chairs are positioned on a concrete terrace, offering unobstructed views of the caldera. Two lanterns with flickering candles provide ambient lighting as the sun sets over the water, creating a serene space for relaxation.

5 out of 5 average rating, 144 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.