Vacation rentals in Sikinos

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Top-rated vacation rentals in Sikinos

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Top guest favorite

A charming outdoor seating area is presented, featuring a small round table surrounded by two light blue chairs. The entrance showcases traditional blue double doors, with decorative touches including potted plants and stone walls, enhancing the inviting ambiance of the space.

Apartment in Paros

4.89 out of 5 average rating, 294 reviews

Βougainvillea house

Ground-floor apartment of traditional Cycladic style, in the heart of the settlement of Parikia. Ideally situated, it offers tranquility and relaxation, and convenient central location. In walking distance: all the interesting sight (old market, frankish castle), bakery, shops. The sea is at a few meters distance from the house, and in 2 minutes you can reach the sea-side street, where you can enjoy the sunset view. The port, the bus station and the taxi stand are at 3 minutes’ distance on foot.

Guest favorite

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.

Cycladic home in Oia

4.95 out of 5 average rating, 356 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

Top guest favorite

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.

Villa in Pyrgos Kallistis

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!

Guest favorite

A serene outdoor terrace features a stone table set for two, accompanied by comfortable seating. Candles provide a soft glow at dusk, with a view of a cliffside village and the deep blue Aegean Sea in the background. The evening sky transitions to a twilight hue.

Castle in Folegandros

4.94 out of 5 average rating, 102 reviews

Folegandros-Cliffhouse

A historic Venetian house with sea view right in the heart of the Castro. The 800 year old house is located in the main village of the island “Chora “ and it is part of the Venetian Castle – called the Castro, located right on the edge of a high cliff, offering a breath-taking view of the Aegean from it’s two magic sea view verandas. An ideal place to stay as it is the heart of the Village – centrally located – and simultaneously a quite place to stay – as no cars can enter the Castro Area.

Guest favorite

A private outdoor plunge pool is accompanied by a series of whitewashed walls and steps leading upward. The scene features a bright blue dome visible in the background, framed by clear skies, with a ceramic pot placed nearby.

Guest suite in Oia

4.97 out of 5 average rating, 164 reviews

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 features a private outdoor plunge pool. Its interior is a unique space with a double bed and a living room. It has stunning view to the caldera and the two iconic blue domes of Oia. Santorini International Airport is about 17 km from Oia Spirit, and the Ferry Port at about 23 km.

Guest favorite

An inviting private jacuzzi is set within a sleek, white-walled niche, featuring soft curves and a tranquil turquoise interior. Natural light reflects off the water's surface, creating a serene atmosphere for relaxation.

Cave in Finikia

4.89 out of 5 average rating, 103 reviews

Cave Suite - Oinos Luxury Suites

Located in the picturesque village of Finikia, Oinos Luxury Suites offers this historical family wine Cavern that has been renovated into a beautiful, modern Cave Suite. Featuring a king size bed & 2 sofa beds, the suite can comfortably sleep 3 adults or 2 adults with 2 children. Other features include the private terrace with Jacuzzi for private use along with sunbeds and sea views. Individually controlled A/C, Nespresso Coffee machine, Smart TV, WiFi & large bathroom with rain shower.

Top guest favorite

An outdoor dining area is featured under a shaded pergola, with a wooden table surrounded by four light wooden chairs. The tranquil waterfront setting offers views of calm blue waters and nearby white structures, providing a serene backdrop for meals.

Cycladic home in Milos

4.99 out of 5 average rating, 112 reviews

Achinos By The Sea Milos

Did you spent your time working on stressing situations away from your family and friends? Do you feel like you need time away from the everyday routine? “Achinos By the Sea” is the place for you and your fellowship! Spend your vacation at this traditional Sirma (boat-house) and get in line with the sound of the sea and the waves. Let the pure north Aegean wind take away all your consideration!Take advantage of our Greek hospitality and let your self travel like the summer breeze!

Guest favorite

An outdoor seating area is highlighted by a coffee table surrounded by soft, white lounge chairs. A private jacuzzi can be seen in the background, with a stunning view of the blue ocean and distant islands. A pergola provides shade, enhancing the relaxing atmosphere.

Dome in Fira

4.93 out of 5 average rating, 241 reviews

FIRA WHITE RESIDENCE DELUXE VILLA

A fully-equipped villa with an attic. With its wide veranda [40m²] and the irresistible combination of stone - exterior and modern - interior, it accomplishes the perfect mix & match of the local traditional architectural style with the most modern touches. It is made up of two bedrooms, the first one [14m²] being carved in the heart of a Santorinean rock, with a concrete bed, commodes and a TV set, and the second bedroom [12m²] featuring a black iron bed with commodes.

Top guest favorite

A private plunge pool is showcased beneath a bright blue sky, with expansive views of the shimmering sea and distant islands. Lush greenery and a cactus are visible near the pool, adding natural elements to the serene outdoor space.

Cave in Oia

4.95 out of 5 average rating, 375 reviews

Sunset Cave House by Spitia Santorini

Embrace the quintessential Santorini experience at the Sunset Cave House, a magical retreat carved into the volcanic rock of Oia's caldera cliff. This traditional yet luxuriously appointed accommodation offers unparalleled panoramic views of the Aegean Sea and the world-famous Oia sunset from your private outdoor plunge pool. Accommodating up to 3 guests, it promises an intimate and unforgettable stay where every moment is bathed in the island's unique light.

Top guest favorite

A private terrace offers a view of the shimmering Aegean Sea, framed by the surrounding caldera cliffs. A plunge pool in inviting turquoise reflects the clear sky. Two elegant flutes stand beside a bowl of fresh fruit, inviting relaxation and enjoyment.

Cave in Oia

4.99 out of 5 average rating, 125 reviews

Cave Villa With Heated Plunge Pool & Caldera View

A traditional cave villa with modern touches that can accomodate up to four people with spacious veranda and breathtaking caldera views. Lathouri Cave Villa is perched on the famous caldera cliffside overlooking the Aegean sea and the two volcanic islands Palia and Nea Kameni. The traditional cycladic architecture along with the unique scenery makes it the perfect choice for those who want to enjoy a relaxing vacation in the lap of luxury.

Guest favorite

A figure stands at the edge of an infinity pool, silhouetted against a vibrant sunset over the caldera. The calm water reflects the warm colors of the sky, creating a serene atmosphere that enhances the natural beauty of the surrounding landscape.

Cycladic home in Megalochori

4.98 out of 5 average rating, 138 reviews

Ambeli Sunset/private heated pool & breakfast

Ambeli Sunset Villa's unique allocation provides the famous sunset view of the caldera avoiding the overcrowding of the well-known cities of Santorini. A newly anti-seismic constructed building covering all the official guidelines to maximize the security of our guests. Depending on the chosen room type that fits you, guests will experience the use of the heated pool or the hot tub in maximum privacy as no facilities are public.

Top guest favorite

An outdoor seating area features two wooden chairs with a small table between them, set under a wooden pergola. The sea is visible just beyond, with clear blue water and a sandy shoreline in the background. A peaceful atmosphere is created by the surrounding natural beauty.

Cycladic home in CYCLADES

4.95 out of 5 average rating, 141 reviews

Manolis And Filio Home -By The Sea

Μanolis and filio home by the sea is on the first floor while on the ground floor there is another independent home (belongs to another owner) The building is right in front of the beach, where you can swim with the most beautiful the sunset. The home is 5 minute walk from Alogomandra, one of the most exciting beaches in Milos.