Cycladic house vacation rentals in Pyrgos Kallistis

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.

4.95 out of 5 average rating, 415 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

ValueLocationBathroom

4.99 out of 5 average rating, 176 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 Merovígli

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.

ValueLocationWalkability

Cycladic home in Pyrgos Kallistis

An inviting private Jacuzzi is surrounded by smooth white walls, creating a tranquil atmosphere. Sunlight reflects off the water, while a tall cactus adds a touch of greenery. Stone seating offers a comfortable space for relaxation, completing this serene outdoor setting.

4.96 out of 5 average rating, 102 reviews

Deluxe Two Bedroom Villa with private Jacuzzi

As seen in the Michelin Guide Embrace Authentic Elegance in Timeless Pyrgos: A Luxury Haven of Tradition, Slow Living, and Heritage Discover a resplendent abode in the heart of Pyrgos village, where the allure of tradition meets modern luxury. Immerse yourself in slow living amidst the captivating heritage, embracing the art of savoring each moment. Experience authentic elegance in our haven of tranquility, where the past whispers its secrets and the present promises cherished memories.

LocationFamilyAir conditioning

4.91 out of 5 average rating, 140 reviews

A Greek Fisherman's House is depicted, featuring a white exterior with a red-tiled roof and three sets of blue windows, facing the beach. The surrounding area includes lush greenery, and additional buildings can be seen in the background against a clear blue sky.

Tiny home in Gytheio

Authentic Greek Fisherman's House 1 - Summer Love

This house has a full fridge and a private balcony, no guests pass through your balcony. Please also check "Love House" and "Love Nest" Houses for availability. House is on the beach. This place is good for couples, solo adventurers, LGBTQ+ firiendly, business travelers and pet firendly. You will wake, eat, live, sleep, dream on the beach! Place is unique, it is like living on a Yacht with the luxury of a house. Now it is divided in three separate houses, sharing the same beach.

FamilyLocationIndoor spaces

4.91 out of 5 average rating, 174 reviews

A private Jacuzzi tub is positioned on a balcony, with a stunning view of the Aegean Sea and a sunset reflecting on the water. Soft clouds are visible in the sky, and a rolled towel is neatly placed beside the tub.

Villa in Vourvoulos

Levantis Suite - Private Hot Tub & Sea View

Levantis Suite (57 sq.m.) at La Estrella Luxury Suites embodies refined Cycladic elegance, perched in serene Vourvoulos just 600 m from Imerovigli. Offering uninterrupted Aegean Sea views, it features a heated private jacuzzi on the balcony, exquisite décor, premium amenities, daily housekeeping, and private parking. Ideally located near a mini market (400 m) and charming local tavernas (350 m), the suite is only 1.3 km from the Caldera, set in a peaceful and quiet area of Santorini.

LocationValueHeating

Cycladic home in Pyrgos Kallistis

A private infinity pool is situated on the terrace, offering unobstructed views of the sea and surrounding hills. The pool water reflects the sky, while lush greenery and rocks frame the area, creating a serene environment.

4.94 out of 5 average rating, 230 reviews

Delilah Villa with outdoor swimming pool

Delilah Villa can accommodate 5 people, has 2 bedrooms with a double bed, and a sofa in the living room. It has a special decoration and a large bathroom with a shower. Its terrace is very large with great views, a private pool, a seating area and sun loungers. Right in front of the villa there is a private parking lot. Quiet neighborhood with privacy and great views. It is also close to Pyrgos Square, just 200 meters away, where the market, restaurants and cafes are located.

ValueFamilyView

4.92 out of 5 average rating, 189 reviews

A person is seated on a terrace overlooking a vibrant sunset. The view includes distant hills and the sea, while a rustic table holds a variety of fresh fruits. A glass holds a drink, reflecting the warm colors of the sunset.

Dome in Pyrgos Kallistis

Calliope's Villa with jacuzzi

Calliope's villa, featuring a jacuzzi and stunning sea views, is located in the charming village of Pyrgos, just 100 meters from the main square, where you'll find restaurants and supermarkets. Santorini's city center (Fira) is only a 10-minute drive away (5 kilometers). This fully equipped, two-story house is ideal for families and groups of friends, offering 3 bedrooms, 2 living rooms, 2 bathrooms, 2 kitchens, a relaxing jacuzzi and a magical view from the upper floor.

FamilyLocationKitchen

4.99 out of 5 average rating, 233 reviews

A private terrace features comfortable seating with plush cushions, small wooden table, and decorative bottles. The space provides a clear view of the deep blue ocean and surrounding caldera, complemented by the whitewashed buildings of Oia in the background and a bright blue sky.

Guest suite in Oia

Suite with 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. Right out of a post card between the two iconic blue domes of Oia. This suite has a private terrace with astonishing panoramic view to the caldera and the blue domes. Santorini International Airport is about 17 km from Oia Spirit, and the Ferry Port at approximately 23 km.

LocationValueTV

Guest suite in Pyrgos Kallistis

4.89 out of 5 average rating, 205 reviews

Luxury Suite| Private Infinity Pool & Volcano View

Enjoy complimentary breakfast delivered to your suite every morning. Relax by your private infinity pool, exclusively reserved for your stay, while admiring breathtaking panoramic views of the volcano, the Aegean Sea and Santorini. Due to the open caldera hillside setting ,the pool area may be visible from some surrounding outdoor areas due to the open caldera setting. Perfect for couples seeking tranquility, comfort and unforgettable sunsets.

LocationFamilyHospitality

4.98 out of 5 average rating, 191 reviews

A modern villa is presented with a distinctive white dome roof, surrounded by greenery and blue sea views. A shaded patio features sun loungers beside a small swimming pool, providing a relaxing outdoor space. The bright blue doors complement the serene landscape.

Dome in Oia

MyBoZer Twins Odyssey Heated private pool

Our brand new My Bozer twin villas are located by the sea, right at the entrance of the famous Oia village. Villa Iliada and villa Odyssey can host couples, families or group of friends, offering all necessary amenities that will guarantee a relaxed, private holidays in the most beautiful place on earth, Santorini island! You can either book one (up to 6 guests) or both villas (12 guests) if you wish to spend holidays with friends

LocationFamilyParks

Cycladic home in Megalochori

An outdoor area features a stonewall backdrop with a staircase leading to a door. A circular hanging chair and a dining set with gray chairs are present. Cushions are arranged on a raised platform, while a tray with fruits is placed on the table.

4.93 out of 5 average rating, 178 reviews

Antonio Caves

Antonio Caves are a typical example of Santorinian architecture. Constructed in 1901, it was initially used as cave house wine preparation cellar and a bakery built right into the volcanic rock. In 2020 it was renovated completely and converted into 3 autonomous suites sharing a common courtyard Situated in the traditional village of Megalochori in two minutes walking distance from the picturesque square of the village

FamilyValueWalkability

Superhost

An infinity pool glistens in the sunlight, with a wooden pergola providing shade over a lounge area. The surrounding landscape is characterized by hills and a clear blue sky, enhancing the serene atmosphere of the villa.

Cycladic home in Santorini

4.83 out of 5 average rating, 117 reviews

Bluewhite villa with heated private pool

Situated in the traditional village of Pyrgos Kallistis, the heart of Santorini island, my place offers a stunning panoramic view of sunrise and the Aegean Sea. The 130m² Villa features luxury, privacy, easy access and comfort in Cycladic style combined with modern design and decoration. Our new infinity pool is a must! Please note that the pool is functional only for the spring and summer season March 15- October 31st

LocationFamilyHot tub

Popular amenities for Pyrgos Kallistis cycladic house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly cycladic house rentals

4.97 out of 5 average rating, 178 reviews

A wooden table is set outdoors, featuring a glass pitcher filled with water and several glasses. A small dessert on a decorative tray is also displayed. Two white chairs complement the arrangement, surrounded by natural stone flooring and greenery.

Home in Spetses

Theros Guesthouse Spetses

ValueFamilyGetting around

4.93 out of 5 average rating, 419 reviews

A panoramic view captures the deep blue sea contrasting with the rugged cliff, dotted with white buildings and blue-domed roofs. A cruise ship glides smoothly across the water, while the picturesque landscape of the caldera extends toward the horizon.

Home in Oia

VILLA MATILDE-VOLCANO VIEW

LocationValueLaundry

Cycladic home in Cherronisos

The image displays a coastal property situated alongside tranquil waters. The building features a combination of blue and white hues, with multiple levels visible against a rocky hillside. Clear blue skies reflect on the water's surface, contributing to a serene coastal ambiance.

4.99 out of 5 average rating, 100 reviews

Dream Sea Moschou #1

LocationFamilyNearby

A private terrace overlooks the caldera, featuring a round table and two wooden lounge chairs. The minimalist white surface contrasts with the blue sea and sky, enhancing the serene view of distant islands and a passing boat.

4.97 out of 5 average rating, 472 reviews

Unique Architecture, the Sculptor's by Cycladica

FamilyValueCleanliness

4.99 out of 5 average rating, 127 reviews

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.

Cycladic home in Milos

Milos By The Sea – Seafront House

ValueLocationWifi

4.99 out of 5 average rating, 212 reviews

By the Mill, Caldera, Oia

ValueLocationWifi

4.97 out of 5 average rating, 116 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 in Emporeio

Canava Villas II - Heated Pool - Santorini

ValueLocationCheck-in

4.94 out of 5 average rating, 147 reviews

A dining set with a glass table and two chairs is positioned on a patio, offering a view of the bay and surrounding hills. Sailboats can be seen in the calm water, while white-washed buildings line the waterfront.

Cycladic home in Sifnos

Thodoris Home,Kamares

FamilyLocationSleep quality

Cycladic house rentals with a patio

4.94 out of 5 average rating, 16 reviews

Home in Pyrgos Kallistis

Thiro Exclusive Villa in Pyrgos

LocationAccuracyCondition

4.98 out of 5 average rating, 58 reviews

A spacious terrace features stylish wooden sunbeds, offering uninterrupted views of the Aegean Sea. The rustic stone pillars and overhead wooden trellis enhance the outdoor setting, creating an inviting space for relaxation or gatherings.

Cycladic home in Artemón

Blue Calm Luxury Villa in Sifnos

FamilyLocationAir conditioning

4.95 out of 5 average rating, 39 reviews

A private outdoor hot tub is positioned on a terrace with sweeping views of the caldera and the sea. Two lounge chairs are arranged nearby, creating a serene space for relaxation. The clear blue water of the hot tub contrasts with the bright sky.

Home in Merovígli

Aethria Villa in Imerovigli

ValueFamilyHiking

5.0 out of 5 average rating, 7 reviews

A serene infinity pool reflects the evening sky, with a gently glowing turquoise hue. White walls of the villa provide a modern contrast against the twilight, while steps lead up to the entrance. Soft lighting enhances the tranquil atmosphere.

Villa in Paros

The Edge -House 1

FamilyLocationNearby

5.0 out of 5 average rating, 15 reviews

A serene view of the sea reflects sunlight under a clear blue sky. An infinity pool appears to blend into the horizon, creating a seamless connection with the water. Mountains are faintly visible in the background, enhancing the tranquil atmosphere.

Villa in Aegina

Villa Melandrina

LocationFamilyWalkability

5.0 out of 5 average rating, 23 reviews

An outdoor dining area features a spacious table for 10 guests, illuminated by warm lighting against a backdrop of rustic stone walls. Sun loungers are arranged by the edge of a tranquil swimming pool, reflecting the evening sky.

Villa in Kastraki

Villa Anali, Kastraki, Naxos

FamilyLocationPool

5.0 out of 5 average rating, 21 reviews

The entrance to Katina's Atelier features a pair of elegant double doors with diamond-patterned glass. Lush orange flowers cascade from above, adding a vibrant touch to the white wall. A small decorative tree is placed beside the entry, enhancing the welcoming ambiance.

Cycladic home in Paros

Katina’s Atelier

LocationFamilyCleanliness

4.97 out of 5 average rating, 37 reviews

The white structure of the house is prominently set against a backdrop of vibrant blue water and clear skies. Olive trees and natural landscaping surround the property, creating a serene connection to nature and offering stunning views of the sea and distant landmasses.

Home in Nisi

Private Beach House Greece

LocationFamilyHiking

Cycladic house rentals with a washer and dryer

Superhost

An outdoor hot tub, filled with clear water, is positioned against a backdrop of the Aegean Sea and the picturesque Mykonos coastline at sunset. Soft hues of pink and orange fill the sky, reflecting on the water, enhancing the serene atmosphere.

Cycladic home in Mykonos

4.95 out of 5 average rating, 156 reviews

The Lovers Seaview Suite with Outdoor Hot Tub

ValueFamilyDecor

A view from the terrace features a custom-built hot tub with clear water, surrounded by whitewashed walls. In the background, a traditional blue-domed church tower stands prominently against a serene sea and sky, capturing the charm of the Oia landscape.

4.96 out of 5 average rating, 256 reviews

Bluedome Suite by Otium Villas Santorini

FamilyValueAccess

4.91 out of 5 average rating, 151 reviews

The private terrace features a heated pool with crystal-clear water, overlooking a panoramic ocean view. Nearby, sun chairs are positioned to enjoy the scenery. Whitewashed walls and natural stone elements enhance the serene ambiance of the outdoor space.

Dome in Oia

Deluxe Villa with outdoor Jetted Tub & Sea View

ValueLocationComfort

4.75 out of 5 average rating, 106 reviews

A serene view of a calm sea under a clear blue sky is captured. The water appears still, reflecting the sky’s hues. Rocky shores define the landscape, while gentle waves lap against the stones, creating a peaceful coastal ambiance.

Home in Naxos

Seaside House At The Town Of Naxos

LocationValueCleanliness

4.99 out of 5 average rating, 111 reviews

A spacious living area features a large blue sectional sofa adorned with yellow cushions, accompanied by a wooden coffee table. A handmade stone fireplace is visible in the corner, and warm light fixtures hang from the ceiling. A television and decor elements enhance the welcoming atmosphere.

Apartment in Naxos

Best Friends & Fam apt,Town of Naxos,by NaxosVibe

FamilyLocationAir conditioning

Cycladic home in Foinikiá

A charming outdoor courtyard is featured, hosting a large table surrounded by chairs with pink accents. The area is filled with decorative plants and a backdrop of white walls and blue doors. Sunlight is gently filtered through a large canopy overhead.

4.9 out of 5 average rating, 262 reviews

Villa Florina

ValueFamilyIndoor spaces

4.98 out of 5 average rating, 104 reviews

A spacious living area features a cozy seating arrangement with a grey sofa and an orange chair. A round dining table is set with glassware, and vibrant chairs are positioned around it. The warm wooden ceiling enhances the room's inviting ambiance.

Home in Lavreotiki

Magda's house

LocationFamilyDecor