Vacation rentals with breakfast in Pyrgos Kallistis

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Top-rated breakfast rentals in Pyrgos Kallistis

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Top guest favorite

A sunlit terrace is featured, adorned with minimalist black loungers positioned for relaxation. The whitewashed walls create a bright contrast against the clear blue sky, while distant views of the sea can be seen at the horizon.

Cycladic home in Pyrgos Kallistis

4.98 out of 5 average rating, 256 reviews

Olyra Traditional Cave Houses

The traditional residences Olyra Traditional Houses, are in the heart of the medievial settlement of Pyrgos, very close to the imposing Kasteli (castle). A three minute walk in the stone laid pavements and side strees is enough to go from Olyra to the central parking of the village as well as the central square. Our houses are created in the same place where the bakery of the village was two centuries ago, with great respect and attachment to Santorinis¨ architecture. The decoration is character

Top guest favorite

A private heated pool is seen on a terrace, offering unobstructed views of the deep blue sea and distant islands. The scene includes iconic white buildings with blue domes, set against a clear sky, showcasing typical Santorini architecture.

Cycladic home in Oia

4.95 out of 5 average rating, 360 reviews

Island blue, postcard perfect view & private pool

Traditional cave house located in the most famous location in Santorini Island with breathtaking postcard perfect views of the blue domed churches! 2 bedrooms, double beds 2 cave bathrooms. Outdoor heated pool with view! Next door to Santorini blue, Eternity & new home Serenity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities. Our other villas Santorini blue,Eternity,Serenity,Captains blue, Secret garden,Sailing & Sky blue

Top guest favorite

An outdoor space features two lounge chairs facing an infinity pool that overlooks the sea. Lush greenery surrounds the area, while a clear sky adds brightness to the scene. The pool reflects the serene blue of the water, creating a tranquil atmosphere.

Villa in Pyrgos Kallistis

4.99 out of 5 average rating, 116 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 favorite

A heated plunge pool is featured within a uniquely shaped archway, with clear blue water reflecting the sun. A stunning view over the ocean and distant islands is visible through the opening. Decorative cushions and a small table with refreshments enhance the inviting atmosphere.

Villa in Imerovigli

4.99 out of 5 average rating, 147 reviews

Ventus Paradiso Villa, Outdoor Heated Plunge Pool

Our cave villa comes with sentimental value as it belonged to our grandmother. Dated back to 1920's brings a great heritage. The villa was totally renovated in 2015, transforming a traditional cave into a luxury residence following faithfully the unique cycladic architecture with exceptional modern esthetics. The villa consists of two bedrooms with ensuite bathrooms, a dining area and a small kitchenette. It features a heated plunge pool and an upper terrace with panoramic view over Caldera.

Top guest favorite

A private outdoor plunge pool is accompanied by a series of whitewashed walls and steps leading upward. The scene features a bright blue dome visible in the background, framed by clear skies, with a ceramic pot placed nearby.

Guest suite in Oia

4.97 out of 5 average rating, 168 reviews

Suite with Outdoor Plunge Pool & Blue Domes View

Located in the very heart of Oia, at a secluded position on the famous caldera of Santorini, Oia Spirit is a stylish complex of 8 stand-alone traditional cave houses, with access to a shared cave pool. This suite features a private outdoor plunge pool. Its interior is a unique space with a double bed and a living room. It has stunning view to the caldera and the two iconic blue domes of Oia. Santorini International Airport is about 17 km from Oia Spirit, and the Ferry Port at about 23 km.

Top guest favorite

An indoor hot tub features calming blue water, framed by a large archway that opens to breathtaking views of the caldera and surrounding landscape. Soft lighting from candles enhances the serene ambiance, complemented by a potted plant placed nearby.

Apartment in Oia

4.98 out of 5 average rating, 225 reviews

BLUE ART CAVES - Stellar Sun Suite with Hot-tub

This elegant suite is perched on the cliffs of the caldera in Oia. It combines traditional Cycladic architecture with a minimal decorative style, making it the perfect choice for those who want to relax. The suite features a private outdoor cave hot tub, offering privacy along with stunning views of the caldera and volcano. Breakfast is included in the price. The room is equipped with air conditioning, free Wi-Fi, coffee and tea-making facilities, bath amenities, and a smart TV.

Top guest favorite

A private plunge pool is showcased beneath a bright blue sky, with expansive views of the shimmering sea and distant islands. Lush greenery and a cactus are visible near the pool, adding natural elements to the serene outdoor space.

Cave in Oia

4.95 out of 5 average rating, 376 reviews

Sunset Cave House by Spitia Santorini

Embrace the quintessential Santorini experience at the Sunset Cave House, a magical retreat carved into the volcanic rock of Oia's caldera cliff. This traditional yet luxuriously appointed accommodation offers unparalleled panoramic views of the Aegean Sea and the world-famous Oia sunset from your private outdoor plunge pool. Accommodating up to 3 guests, it promises an intimate and unforgettable stay where every moment is bathed in the island's unique light.

Top guest favorite

An arched window frames a serene view of the mountains and sea. A private heated jacuzzi and two light-colored bean bags are positioned on the terrace, complemented by potted plants. The natural light enhances the minimalist design of the outdoor space.

Apartment in Pyrgos Kallistis

5 out of 5 average rating, 200 reviews

Star Infinity Suite with private heated Jacuzzi.

Star Santorini Infinity Suites is brand new complex of 3 suites each one with private heated jacuzzi and one shared swimming pool. An exclusive location provides a marvelous seashore&mountain landscape. This Suite is with two bedrooms (one bedroom is loft style bedroom). Two bathrooms,one living area with kitchenette,two balconies,one private jacuzzi and one shared swimming pool.Greek breakfast (only from local fresh products) is served every morning.

Top guest favorite

A private terrace offers a view of the shimmering Aegean Sea, framed by the surrounding caldera cliffs. A plunge pool in inviting turquoise reflects the clear sky. Two elegant flutes stand beside a bowl of fresh fruit, inviting relaxation and enjoyment.

Cave in Oia

4.99 out of 5 average rating, 130 reviews

Cave Villa With Heated Plunge Pool & Caldera View

A traditional cave villa with modern touches that can accomodate up to four people with spacious veranda and breathtaking caldera views. Lathouri Cave Villa is perched on the famous caldera cliffside overlooking the Aegean sea and the two volcanic islands Palia and Nea Kameni. The traditional cycladic architecture along with the unique scenery makes it the perfect choice for those who want to enjoy a relaxing vacation in the lap of luxury.

Guest favorite

A private terrace showcases a hot tub with sweeping views of the sea and surrounding landscape. A cozy lounge area, adorned with patterned cushions, invites relaxation under an archway, while a sunhat rests nearby, complementing the tranquil ambiance.

Cycladic home in Oia

4.93 out of 5 average rating, 155 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.

Guest favorite

An upper balcony features a private hot tub alongside a jetted plunge pool, both overlooking a serene landscape. A panoramic view includes the sea and distant islands, with soft hues of twilight casting a tranquil ambiance.

Cave in Fira

4.94 out of 5 average rating, 109 reviews

Villa Cloud, Heated private pool, Caldera view

This exceptional villa is 75 Sq.m, originally built inside volcanic soil has now been reconstructed with a luxurious contemporary futuristic twist. This unique property with its innovative space and surreal construction is embodied with sound motion and visual essence. The villa comprises of a fully equipped kitchen and dining/lounge area which overlooks an intoxicating volcanic view, and peaceful mesmerising sea view.

Top guest favorite

A spacious terrace showcases two comfortable lounge chairs facing the breathtaking views of the Aegean Sea, caldera, and volcanic islands. The serene blue waters contrast with the white architecture surrounding the area, offering a perfect spot for relaxation and contemplation against a clear sky.

Cycladic home in Akrotiri

4.99 out of 5 average rating, 174 reviews

Akrorama Spilia-Ultimate Privacy,Pool&Caldera View

This exclusive suite features a completely private cave heated pool and secluded yard, ensuring full discretion and serenity. Ideal for guests who value privacy, it also offers a breathtaking, unobstructed view of the sea, caldera, and volcanoes, a truly unique Santorini experience. Daily breakfast is included and served in your suite. Daily cleaning service available.