Cycladic house holiday rentals in South Aegean

An outdoor terrace features a private heated Jacuzzi and sun loungers, framed by traditional Cycladic architecture. Soft, neutral tones are complemented by gentle lighting. A wooden ladder leans against the wall, leading to the upper level, while distant white buildings create a scenic backdrop.

4.95 out of 5 average rating, 306 reviews

Helianthus Honeymoon Hideaway House

Our Honeymoon House with Caldera View offers the perfect romantic escape in Santorini, with the graceful addition of a heated outdoor Jacuzzi (will be closed between 15/11-15/3) providing the ultimate sense of relaxation overlooking the majestic caldera and the infinite Aegean blue. In an ample space of 40m2 divided into two levels, it provides everything a couple may desire. It has been built in perfect alignment with the distinct Cycladic architecture and boasts unparalleled, absolute privacy

4.96 out of 5 average rating, 109 reviews

An open-plan living area featuring textured stone walls and a high arched ceiling. A wooden dining table is surrounded by chairs, with a modern kitchen visible in the background. A cozy seating area offers comfortable sofas, while a small plunge pool is nestled in one corner.

Earthen home

Canava Villas II - Private Pool - Santorini

Villa#2 comes in 2 level floors and accommodates up to 6 people. On the ground floor there is a master bedroom, bathroom, fully equipped kitchen, lounge and WC. The upper floor provides 4 single floor mattresses or 2 double ones & its own bathroom. Outdoor private pool with Jacuzzi, patio, dinning area and sun lounges! Welcome drinks, basket of seasonal products, Nespresso coffee, Concierge services, A/C, Netflix, daily housekeeping, laundry services and many more amenities are waiting for you!

4.97 out of 5 average rating, 294 reviews

The private veranda features a hand-paved stone floor, offering unobstructed views of the sea and caldera. Two deck chairs invite relaxation under the bright sky, alongside a small dining table with wooden chairs. The serene atmosphere highlights the natural beauty of the surroundings.

Cave

Historic cave house, the old bakery by Cycladica

The old bakery of the village awaits just two minutes from Oia's central square, with a private entrance right on top of the stairs that lead to Armeni bay. Carved in the mountain with respect to the unique local architecture and in harmony with the sun-filled, wild volcanic beauty, the newly restored cave house recounts stories of tradition, heritage and style. The red pumice stones, antique marble floors and handcrafted wooden furniture, create the feeling of an authentic warm hospitality.

4.98 out of 5 average rating, 214 reviews

A private terrace features a refreshing plunge pool surrounded by whitewashed walls and wooden lounge chairs. Plush pillows are arranged on a nearby seating area, while the iconic blue domes of Oia are visible against the clear sky, overlooking the expansive sea.

Guest suite

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 additionally features a private outdoor plunge pool. The view from its terrace is stunning, featuring the caldera and the two iconic blue domes of Oia. Santorini International Airport is about 17 km from Oia Spirit Boutique Residences, and the Ferry Port at approximately 23 km.

A bright entryway features vibrant blue doors and walls adorned with planters. Two yellow chairs with colorful cushions are positioned at a small table, complemented by a bicycle mounted on the wall. A cat rests on the tiled floor, enhancing the welcoming environment.

4.98 out of 5 average rating, 128 reviews

Flou House

A unique aesthetic apartment with a beautiful private patio and lots of art touches, located in a picturesque neighbourhood in the heart of Naxos Town that can host up to 5 guests. Located 10' on foot from the Port, 1'-2' from the Market and other places of interest (castle, museums, etc) and entertainment (bars, restaurants, etc). If you travel without a car, no worries; the closest bus station to the most popular beaches and villages is at 3' on foot. Free parking space at 3' on foot!

A spacious living area features a large built-in sofa with neutral cushions and decorative accents. A modern coffee table sits at its center. The kitchen is visible in the background, equipped with essential appliances and light cabinetry. Soft lighting enhances the inviting atmosphere.

4.91 out of 5 average rating, 233 reviews

Traditional Antigoni's house

The apartment is only 600m from the port. 50 m away from the house there is a traditional greek tavern . Supermarket, bakery and other shops are available a fev metres away of the house. The organised and sandy beach of Papikinos is only 400 metres on foot. .Το διαμέρισμα βρίσκεται 600 μέτρα από το λιμάνι του Αδάμαντα,στα 50 μέτρα βρίσκεται ένα παραδοσιακό ταβερνάκι.Στα 200 μέτρα υπάρχει σούπερ μάρκετ και άλλα μαγαζιά. Η αμμώδης, οργανωμένη παραλία του Παπικινού είναι στα 400 μέτρα.

A private plunge pool is visible in the foreground, reflecting clear blue water. The stunning caldera view features vibrant blue dome churches in the distance, with the Aegean Sea stretching out toward a clear sky. Whitewashed buildings create a serene backdrop.

4.98 out of 5 average rating, 285 reviews

Santorini blue, caldera views, private pool

Traditional Santorini cave house with famous blue dome churches, postcard perfect caldera views in the heart of Oia. next to main path.. Private plunge heated pool with panoramic views. Next to Island blue, Serenity &Eternity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities Other villas : Island blue, Eternity,Serenity,Captains blue, Secret garden, Sailing &Sky blue Flexible on pandemic related cancellations!

Two white, high-back stools are positioned beside a railing overlooking the sea, with a scenic view of rocky shores and distant mountains. A decorative tray holds two cups, complemented by a pair of sunglasses resting nearby, suggesting a relaxed outdoor environment.

5 out of 5 average rating, 108 reviews

Milos By The Sea - Eco House

"Milos By The Sea" is a brand new, traditional solar powerhouse, 100% eco-friendly, located in a fishing village only 600 meters from Plathiena beach. It is an Eco friendly house as it is completely powered by solar energy. The picturesque settlement called "Areti", provides an exquisite view, since it is surrounded by the beauty of nature. Waking up to the sound of the waves is a unique experience for our guests who need to enjoy absolute tranquility during their vacation.

An infinity pool gently merges with the shimmering caldera below, framed by an elegant archway. The water reflects a tranquil blue, inviting relaxation while offering sweeping views of the volcanic landscape that surrounds.

5 out of 5 average rating, 216 reviews

Akrorama Anemos - Private Pool & Caldera View

Anemos suite is located in Akrotiri overlooking the caldera and the volcanic islands . It is a suite with Private, Infinity heated Cave style plunge pool with Jet system and private patio. There is a king size bed that can accommodate two person. Daily breakfast is included and served in your suite . There is a cleaning service included. Inform us about your arrival details in advance , we can arrange a taxi/transfer for you.

A spacious bedroom is showcased, featuring a large bed with a dark gray blanket. The open layout reveals a bright living area with a kitchenette and seating space, all adorned in soft white tones. Large windows invite natural light and provide views of the surroundings.

4.93 out of 5 average rating, 452 reviews

Divine View Sun Home

Unwind and relax with a glass of wineadmiring the breathtaking views of the famous Santorinian sunset from this house's private veranda . Awake refreshed and ready for a day to explore the island via this clean, sunny house with impressive views to the caldera , volcano of Santorini Aegean Sea & the island of Thirassia . Head out and wander through the famous paths of Fira and explore the nearby little shops & cafe .

A bright interior space is depicted, featuring a cozy sitting area with a striped bench adorned with yellow pillows. A rustic table and white chairs sit alongside a wall mirror, while large windows offer scenic views of the sea, enhancing the light-filled space.

4.99 out of 5 average rating, 103 reviews

Cozy all-season home with garden & sea views

Welcome to Casa Nidito, a calm and minimalist home inspired by the island’s natural beauty. Built with earthy materials and soft tones, it offers sea views and a Mediterranean garden with a shaded spot to enjoy breakfast or a glass of wine. Inside, everything feels simple, comfortable, and connected to nature. Thoughtful touches and the gentle island breeze make every stay peaceful, grounding, and truly Santorini.

A private terrace features potted plants against a backdrop of the caldera and sea. A plunge pool is visible, with steps leading away toward the water. In the distance, a wooden boat floats peacefully on the calm blue water.