Villa vacation rentals in Pyrgos Kallistis

4.83 out of 5 average rating, 260 reviews

An outdoor dining area is visible, featuring a large table set for several guests. The stone architecture blends seamlessly with a spacious terrace, while light-colored wooden beams highlight the entrance to the indoor space. The setting offers a view of the surrounding rooftops and fading sunset.

Villa in Hydra

The Maisonette - View Historic Hydra in Comfort!

Recently renovated in keeping with historical traditions, our 2 bedroom, 3 bed apt is perfect for vacation travel, adventures, and short trips to the Island. The apartment building is set in a private location - within walking distance to the port, taverns, and supermarkets. Enjoy exquisite mountain, village, and sea views from the balconies and terrace! A great place to stay and explore the Island, or just chill in the sun and relax. Welcome To Hydra, We look forward to hosting your stay!

Superhost

Two glasses of sunset cocktails are placed on a small wooden table beside a reclining chair. A vibrant sunset casts warm hues across the sky and reflects on the calm sea, creating a serene backdrop. A distant island is visible on the horizon.

Villa in Mikri Vigla

4.95 out of 5 average rating, 102 reviews

Naxea Villas I

A state-of-the-art 3-bedroom villa, sited on the scenic hill of Orkos, with a private pool, a stunning sea view and a breathtaking sunset view that stays with you forever. Thanks to their prime location, Naxea Villas wondrously combine the calmness of the Aegean with the refreshing power of the island's mountainous scenery, offering a magical destination for families, couples, groups and digital nomads, and an opportunity to experience Naxos at the epitome of comfort, luxury, and authenticity.

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.

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!

5 out of 5 average rating, 28 reviews

A shaded lounge area features a comfortable wooden chair positioned beside a small, inviting Jacuzzi. In the background, a serene view of clouds and hills is visible under a clear blue sky, creating a calming outdoor environment.

Villa in Tarampados

The Detailor Peak - private luxury villa 3BR/3BA

A unique villa with tranquil views. Inspired by the humble complexity of the Cycladic islands, the 3 en-suite bedroom villa has unobstructed views towards the Aegean sea. The villa has a shaded outdoor living/dining area that can be used throughout the day. This open space encourages socializing in the true spirit of laid-back summer living. A The villa also has a shaded Jacuzzi lounge area . The design and the material pallete is inspired from the island’s tradition and local craftsmanship.

4.99 out of 5 average rating, 146 reviews

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

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.

4.97 out of 5 average rating, 119 reviews

Martynou View Villas

Martynou View villas is a private property,located in Santorini Pyrgos village. Just a few steps away from restaurants cafe and more shops.Only 10 minutes driving distance from central Fira and from the best beaches of the island. This is an ideal choice for couples. The property offers a spacious living room with kitchen, bathroom,double bed,air condition,coffee machine,TV,fridge,Wi-fi, soundtrack,private parking and a lovely balcony with private heated jacuzzi and stunning sea view!

4.92 out of 5 average rating, 109 reviews

A spacious terrace is visible, featuring two sun loungers positioned towards a scenic coastal view. The sea sparkles in shades of blue, with rocky cliffs and a small sandy beach in the background. Light curtains gently drape from an overhang, framing the serene landscape.

Villa in Kokkala

Amazing view

Όμορφο και άνετο σπίτι με ξύλο και πέτρα που σας ταξιδέυει στην τοπική παράδοση. Διαθέτει δύο κρεβατοκάμαρες με ξύλινο πάτωμα που κοιμίζουν 3 και 4 άτομα αντίστοιχα . Η πρόσβαση σε κουζίνα και μπάνιο γίνεται από την βεράντα όπως φαίνεται στις φωτογραφίες.Έχει κοινή αυλή με το εκκλησάκι που βρίσκεται δίπλα όπου μπορούν να παίζουν τα παιδιά της γειτονίας με ασφάλεια. Έχει πρόσβαση σε αυτήν αυτοκίνητο εώς την πόρτα του σπιτιού για Parking μικρής διαρκείας, απαγορεύται όμως το 24ωρο.

5 out of 5 average rating, 103 reviews

An outdoor patio features comfortable loungers facing the Aegean Sea, providing views of distant islands. A small table with a plant is positioned alongside a textured rug. The open space is shaded by a wooden pergola, and a swimming pool is partially visible in the background.

Villa in Νάξος

Arismari Villas Orkos Naxos

Villa Arismari is located on a serene hillside, surrounded by natural boulders, overlooking the beautiful coast of Orkos. We have a breathtaking panoramic view of the Aegean Sea and our neighboring island of Paros. We are situated between the main beach and smaller bays of Orkos. While enjoying the view that Villa Arismari offers prepare to take your most incredible selfies . Villa Arismari is a beautifully designed villa of Cycladic minimal architecture.

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, 101 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.

4.99 out of 5 average rating, 140 reviews

A stone-built villa stands elegantly against a twilight sky, reflecting calm waters of the swimming pool. Warm lights illuminate the structure, emphasizing its architectural features. Outdoor seating is visible, complementing the tranquil atmosphere created by the surrounding landscape.

Villa in Koroni

Gerakada Exclusive-Seaview Villa with Private Pool

This stunning stone-built villa offers a private pool for ultimate relaxation and is conveniently located near local beaches, restaurants, and amenities such as supermarkets, bars, and taverns. Zaga beach and Agia Triada are located on 6min away! Guests can enjoy free WiFi and parking. It's an exceptional choice for a memorable and relaxing vacation.

Luxe

An outdoor terrace features an infinity pool surrounded by sunbeds with dark towels. A shaded seating area and potted plants enhance the space, while expansive views of the sea and surrounding landscape are visible in the background.

5 out of 5 average rating, 13 reviews

Kamini White 2 Bedroom

Kamini White 2 bedroom, is an Ultra Luxury Villa situated at Pyrgos village overlooking the sea, the sunrise and the nature surroundings. It is fitted with design furnishing and modern smart home amenities. The house combines Cycladic architectural elements with minimal modern design. The services provided in this villa are of the highest standards.