Villa vacation rentals in Pyrgos Kallistis

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Top-rated villa rentals in Pyrgos Kallistis

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Top guest favorite

A spacious terrace is visible, featuring comfortable lounge chairs and panoramic views of the sunset. The living area includes a modern sofa and a wall-mounted television, while a light-filled sleeping area is partially seen through an open doorway.

Villa in Pyrgos Kallistis

4.99 out of 5 average rating, 107 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

Villa in Imerovigli

4.98 out of 5 average rating, 127 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.

Guest favorite

An outdoor shaded dining area is framed by wooden beams, featuring a natural stone wall. A large table is surrounded by comfortable seating, complemented by earthy-toned decor and a woven pendant light. Panoramic views of the sea and greenery are visible in the background.

Villa in Ano Vasilikos

5 out of 5 average rating, 8 reviews

Sea View Private Pool Villa-Montesea Nature Villas

Montesea Villas is located on a private hill called Mytikas, less than a kilometer away from the main road of Vasilikos. It's an ideal place for those who seek tranquility while having the option to visit one of the dozens of beaches located 4-10 minutes away in the Vasilikos area. In addition, with just a 10-minute walk or 3 minutes by road, our guests can have access to convenient stores, groceries, supermarket, traditional restaurants, beach bars, pharmacy, health centre and cafeterias.

Superhost

An outdoor dining area is illuminated by natural light, featuring a large table surrounded by woven chairs. Potted flowers add a touch of color, while expansive views of the landscape and sea stretch into the distance, framed by a pergola-covered terrace.

Villa in Mykonos

4.98 out of 5 average rating, 53 reviews

Villa Vanilla - Mykonos - Private Heated Pool

Villa Vanilla is a stunning construction of the finest quality, boasting a modern chic architectural design. The villa features a private heated Jacuzzi pool measuring 4 by 4 meters and offers breathtaking, unobstructed sea views to Delos, Renia, Tinos, and Syros Cycladic islands. The villa's altitude and orientation provide mesmerizing sunset views while maximizing the duration of natural sunlight. The outdoor space is beautifully enhanced by plants that complement the design.

Top guest favorite

Villa in Kalafati

5 out of 5 average rating, 10 reviews

Stephanie, Heated Pool by Red Windmill Villas

Brand New Villa for Easy Living by the Red Windmill Villas. HEATED POOL & JACUZZI Beautiful unobstructed sea view, seen from all three master bedrooms. Carefully selected details, earthly tones and natural materials in the decoration give a rural touch to the villa. Designed to offer guests a soothing, calming holiday experience. All comforts of modern living provided in a vintage aesthetic. The villa is very close to three beautiful beaches, beach bars-restaurants near by.

Superhost

An outdoor dining area is featured on a terrace with a table set for four, complemented by sleek, golden chairs. The serene view includes the sea, a distant village, and a bright full moon illuminating the night sky.

Villa in Exo Gonia

4.88 out of 5 average rating, 113 reviews

Blue Soul Luxury Villa

Blue Soul Luxury Villa is a sanctuary of elegance in the heart of Exo Gonia. Nestled on the hillside towards Pyrgos, it offers breathtaking views of the Aegean Sea, the village, and the rolling landscapes. Its highlight - a four seat hot tub - invites you to unwind in pure bliss. Thoughtfully designed with curated décor and a seamless blend of comfort and style, the villa promises a unique and tranquil escape, where every detail enhances your Santorini experience.

Superhost

A spacious living area features a blend of traditional wooden furniture and decor elements. Glass-fronted cabinets display items, while a rustic fireplace is the focal point. Natural light fills the room, highlighting the whitewashed walls and stylish lamps.

Villa in Vourkari

5 out of 5 average rating, 4 reviews

Three Bay House - Luxury and Soothing Sea Views

A unique villa where you can lounge and relax away from it all, in one of the most private locations on the island, despite the fact that it is located just 1 klm away from the cosmopolitan marina of Vourkari and 3 klm away from the port. Set on the top of a hill, on a 5000 sq.m. land, it enjoys breathtaking sunset views over Vourkari and the grand blue, and lies only a 10 minute-walk away from a little sandy cove, one of the best beaches on the island, in my opinion.

Superhost

A spacious outdoor terrace is furnished with a wooden dining table surrounded by comfortable chairs. A scenic view of the sea and rolling greenery is visible in the background, enhanced by the natural light filtering through the woven roof.

Villa in Naousa

4.77 out of 5 average rating, 13 reviews

Dream Villa with Views Garden nr Best kid's Beach

After an exhausting day at our local beach (possibly the best beach on the island for small children), you will lounge under the shaded terrace, a magical relaxation spot, with wonderful seaviews at daytime and moon & star views at night. You will be located at the tranquil and exclusive area of Santa Maria in Paros. After a few minutes walk, you will be swimming in the beautiful sandy beaches of Santa Maria, possibly the best beach on the island for small children.

Guest favorite

An outdoor dining area is shaded by a wooden pergola, featuring a long table with a fruit bowl at its center. Sun loungers are positioned nearby, facing an inviting infinity pool that offers stunning views of the Aegean Sea and surrounding landscape.

Villa in Ornos

5 out of 5 average rating, 6 reviews

Villa Gin by Mykonos Mood

A luxury Greek getaway with altitude. Villa Gin like, its twin Villa Tonic is a show-stopper. Luxury at its finest in this top-of-the-hill property with the Aegean sea at its feet. In the highly desirable area of Kanalia, a few minutes from Mykonos town this divine home delivers the summer Greek island high-life we dream about. Linger poolside gazing at ancient Delos, birthplace of Apollo at the sunset sipping your drink of choice as the cerulean Aegean turns pink.

Superhost

A large villa is set against a clear blue sky, featuring a welcoming front staircase. A tranquil pool reflects the surrounding landscape, while lounge chairs are positioned nearby. Lush greenery and a few trees enhance the outdoor area, providing a serene atmosphere.

Villa in Corinthia

4.91 out of 5 average rating, 74 reviews

Luxurious 500m2 Villa Asklipia

Neoclassic Estate, Pool, BBQ, Indoor & Outdoor Jacuzzi, Sauna! Waterfun Park Corinth, Loutraki Casino Resort, Private & Public Beaches + Water Sports, Diving, Cafés, Taverns, Bars, Beautiful Scenery! Surrounded by pine tree forest, under 1-hr from Athens, Easy Access-Few Mins off the motorway! Check Photo Gallery and description for: Olive picking experience (Nov-Jan), Fine wine tasting, historical & tons of breathtaking views at the ancient City of Nemea!

Superhost

A spacious terrace extends along the villa, featuring a combination of wooden dining tables and comfortable seating. Shade is provided by a large umbrella, while the soft glow of sunset reflects off the nearby water, enhancing the tranquil coastal setting.

Villa in Fragkolimano

4.88 out of 5 average rating, 24 reviews

Villa Corali II

A unique villa right on the sea with a sense of Greece, with unrestricted views of the bay, (Fragolimano) this exclusive villa will help you feel the absolute relaxation away from the hustle and bustle of the city. Just a few steps away, down a private path, you can enjoy the crystal clear waters of the bay on a very secluded and quiet beach with your own umbrella and sunbed. Suitable for families, groups of friends but also a romantic trip for 2!

Superhost

A shaded outdoor seating area features a light-colored sofa and a hanging hammock, allowing for relaxation while overlooking a scenic ocean view. Large windows frame the landscape, creating a seamless connection with nature.

Villa in Mykonos

4.91 out of 5 average rating, 23 reviews

Private Villa with private pool Pascal´s Villa

Welcome to our brand new villa!! Located in the luxury part of the Island in Lia area. Make your stay memorable enjoying the best sunsets and the ocean view from your private pool. 4 bedrooms all with private bathrooms and airconditioning. Luxury meets traditional style to make you feel like home. 5-10 minutes driving from Ano Mera,markets and the most of the south beaches. We also arrange any kind of service like private transportation 24/7.