Villa vacation rentals in Pyrgos Kallistis

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.

4.83 out of 5 average rating, 264 reviews

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!

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!

A private heated mini pool is shown against a backdrop of a vibrant sunset, with the sun setting over the sea. Lush greenery and bamboo accents frame the pool area, contributing to a serene outdoor setting.

4.92 out of 5 average rating, 106 reviews

Martynou View Blue

Martynou View is a private villa, 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 the best beaches. This is an ideal choice for couples or small families. Suite offers private parking,a spacious living room with a kitchen, bathroom,double bed,2 aircondition,2 Smart TV,CoffeeMachine,fridge(offer bread jam honey butter),Wi-fi, and private heated mini pool(jacuzzi)with stunning sea views.

A stone wall frames a serene outdoor area featuring a dark pool. The water reflects the subtle colors of the sky at dusk, while distant mountains rise above a tranquil landscape. Soft lighting along the wall enhances the peaceful atmosphere.

5 out of 5 average rating, 107 reviews

Valeria's House

Traditional Cycladic cave - villa made of wood and stone. Panoramic view of Adamas and the port. Large openings allow light to pass unhindered into the space and act as a tableau vivant on the theme of the natural environment. At 40 sq.m. of the interior are included: bedroom, fully equipped kitchen, living room and bathroom. The outdoor area has a swimming pool. Complete privacy, peace and quiet. Central location, 4 minutes from the port and 7 from the airport.

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, 182 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

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.

5 out of 5 average rating, 113 reviews

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.

The image features a well-lit outdoor pool illuminated by soft turquoise lights. A two-story mansion is visible in the background, surrounded by olive trees. The sky is dramatic, with dark clouds gathering, adding depth to the tranquil evening scene.

4.99 out of 5 average rating, 114 reviews

Villa Constantina

Villa Konstantina is a mansion of the modern era in a dynamic Italian line but also a discreet aristocratic finesse. It can accommodate up to 14-16 people. The view of Nafplio, the sea, the huge garden and the pool is outstanding! Villa Konstantina is a modern-era mansion in a dynamic Italian line but also discreet aristocratic finesse. It can host up to 14-16 guests. The view of Nafplio, the Sea, the huge garden and the pool is amazing!

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, 102 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, 155 reviews

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.

A serene coastal view is framed by lush greenery and pine trees. The calm waters of the Argolic Gulf reflect the clear blue sky, while a distant shoreline gently curves into the horizon. The image captures a peaceful connection between land and sea.

4.99 out of 5 average rating, 106 reviews

Beachfront Villa Panos with panoramic sea views

Unique villa in front of the sea in 1 level making the house extremely functional. The surrounding area is beautifully landscaped with gardens where you can enjoy your breakfast, lunch or dinner with a wonderful view of the Argolic Gulf. The location makes it unique as it has direct access to a sandy beach with crystal clear waters.

Superhost

A private outdoor Jacuzzi is situated on a terrace, surrounded by whitewashed walls and overlooking the serene sea. The sparkling water reflects sunlight, creating a tranquil atmosphere. The sloping hillside provides additional views of the coastline and distant boats.

4.89 out of 5 average rating, 472 reviews

SEACREST VILLA-VOLCANO VIEW

SEACREST VILLA has a bedroom with double bed, a living room with 2 single beds, a private fully equipped kitchen, a private shower room and 2 private verandas with perfect view to the Sea ,the Caldera ,the Volcano and the village of OIA.There is also a jacuzzi.

A glass of wine rests on a light-colored surface, accompanied by folded towels in vibrant hues. The background features a tranquil sea at sunset, with soft pastel colors illuminating the sky and distant mountains.

4.88 out of 5 average rating, 146 reviews

Sunset Villa

This is a very cosy place with direct view towards the famous sunset of Milos from the capital of Plaka. It is a two minutes walk from the center, still in a very quite location offering privacy. Right in the traditional village of Plaka!

Popular amenities for Pyrgos Kallistis villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

An outdoor dining area features a wooden pergola providing shade. A rectangular table is set with chairs, surrounded by greenery. Stone pathways lead to the villa, which is adorned with plants and includes a built-in BBQ nearby.

4.96 out of 5 average rating, 56 reviews

Villa Armonia, Sunset View and Relaxing Beach Vibe

4.94 out of 5 average rating, 62 reviews

Infinity sea view hillside villa with private pool

5 out of 5 average rating, 7 reviews

Elia Cove Luxury Villa I

A tranquil outdoor space features a private pool overlooking the Argolic Gulf. Six lounge chairs are positioned near the water's edge, while scenic views of the surrounding landscape and distant islands are visible under clear blue skies.

5 out of 5 average rating, 64 reviews

Villa Anemos

An inviting stone terrace surrounds the infinity pool, offering unobstructed views of the Aegean Sea and nearby islands. Two sun loungers are positioned beside the pool, providing a serene space for relaxation under the sun. Lush olive trees frame the scene, enhancing the tranquility.

4.98 out of 5 average rating, 66 reviews

Villa St. George mit Infinity Pool

A modern home is situated against a backdrop of rugged mountains, featuring a light-colored exterior with large windows. Nearby flowers in various hues add color to the landscape, while an outdoor seating area is shaded by a large awning.

5 out of 5 average rating, 11 reviews

C l e o - Horizon Villas

An expansive terrace features comfortable lounge chairs beside a large swimming pool. Lush greenery and colorful flowers surround the area, while scenic mountain and sea views stretch into the distance. The villa's elegant architecture complements the tranquil outdoor space.

5 out of 5 average rating, 22 reviews

Villa Fantasia Isthmia

An expansive infinity pool is surrounded by palm and olive trees, overlooking the Aegean Sea. The crystal-clear water reflects the blue sky, while a circular tray with refreshments floats on the surface. Sun loungers and a dining area are positioned nearby for relaxation.

4.97 out of 5 average rating, 33 reviews

Sanarte villa 3, 4br w/private pool and sea view!

Luxury villa rentals

An outdoor terrace features a round dining table set with plates and glassware, surrounded by wicker chairs. A cozy seating area with soft cushions is positioned nearby. The background displays a scenic view of rooftops and distant mountains, enhanced by warm sunset lighting.

5 out of 5 average rating, 6 reviews

Villa Kalon -The Heart of Hydra

A private terrace features a shimmering pool with views of the sea and the caldera. Whitewashed buildings in Oia line the cliffside under a clear blue sky, creating a serene backdrop for relaxation.

4.87 out of 5 average rating, 209 reviews

Top Caldera view villa with Hot Tub in Oia

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, 150 reviews

Loukia House

Superhost

4.8 out of 5 average rating, 5 reviews

Cella Villa - Magnolia

The outdoor terrace features comfortable wooden lounge chairs positioned to face the sea. A manicured garden is visible, along with palm trees swaying gently in the breeze. An infinity pool extends into the horizon, reflecting the clear blue sky and tranquil waters.

4.98 out of 5 average rating, 41 reviews

Beachfront Sunrise (Heated) Pool Villa_2

5 out of 5 average rating, 39 reviews

Villa Gaia -Mykonos AG Villas

An illuminated infinity pool reflects the vibrant colors of the sunset, framed by trees. Soft lighting enhances the surrounding area, creating a serene and inviting atmosphere. The view extends out to the horizon, where the sun dips below the landscape.

5 out of 5 average rating, 23 reviews

Villa Amethyst

A tranquil infinity pool nestles against a backdrop of white architecture and vibrant flowers. The pool water reflects the clear blue sky, complemented by a nearby blue-domed church. The scene evokes a serene outdoor space perfect for relaxation.

5 out of 5 average rating, 53 reviews

Luxury Villa BLUE DOME, the 5* villa experience

Villa rentals with a pool

4.88 out of 5 average rating, 8 reviews

Two wooden lounge chairs are positioned beside a plunge pool, with a small table holding a wine glass and a bottle of wine. The view overlooks the Aegean Sea and distant volcanic islands, with soft pastel hues accenting the landscape.

Villa in Oia

Little Rock Villa-Oia. Entire Cave House Oia

A serene outdoor view showcases a chlorine-free swimming pool surrounded by lush greenery. Towering cypress trees and vibrant vegetation add to the natural landscape, while the distant expanse of the Messenian Gulf offers a scenic coastal backdrop under a clear blue sky.

5 out of 5 average rating, 6 reviews

Villa Sadova

A well-maintained swimming pool is surrounded by lush greenery and tree shade. Comfortable lounge chairs are positioned along the poolside, providing a relaxing atmosphere. The clear water reflects the blue sky, creating an inviting scene for guests to enjoy.

4.95 out of 5 average rating, 95 reviews

Melissaki Villas on a hill

An infinity pool extends towards the sea, offering a scenic view of distant mountains and tranquil waters. A person is seen relaxing in the pool, with their back turned, creating a peaceful atmosphere in this beautiful setting.

5 out of 5 average rating, 62 reviews

Eucalyptus Villa

An infinity pool reflects the gradient of the evening sky, bordered by modern lounge chairs. A wicker lantern adds a touch of warmth, while the panoramic view captures the hills and the distant coastline, creating a serene outdoor space.

5 out of 5 average rating, 32 reviews

Eneos Villa #1 Pool & Sea View, Paros

A spacious outdoor area features a clear swimming pool surrounded by stone tiles. Comfortable bean bags are placed near the water, offering a spot to relax. A scenic view of rolling hills and the sea enhances the tranquil atmosphere under a clear blue sky.

4.97 out of 5 average rating, 70 reviews

The Serenity House-Villa Apollon

A private pool reflects the soft glow of exterior lights, surrounded by a stone terrace. The unique structure features a wooden roof, while large windows allow for indoor views. Comfortable lounge chairs are positioned near the water, creating a serene environment.

5 out of 5 average rating, 34 reviews

Celini Villa Tinos

A tranquil evening view showcases an inviting saltwater pool, softly illuminated near a stone terrace. The darkening sky and distant lights reflect on the calm water, with silhouettes of rolling hills forming a serene backdrop.