Vacation rentals with a pool in Santorini Caldera

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Top-rated rentals with a pool in Santorini Caldera

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Top guest favorite
A charming courtyard is displayed, featuring comfortable outdoor seating arrangements and a tranquil infinity pool in the background. The villa's exterior is constructed with local stone, illuminated softly by outdoor lighting, while the sky captures a gradient of blues and wispy clouds as twilight approaches.
Villa in Santorini
4.98 out of 5 average rating, 133 reviews

Spectacular Private Mansion- Car Rental included *

Mansion Kyani is a secluded hillside villa in Santorini's prettiest village. It features three self-contained suites spread over two spacious floors, ensuring distinct private living areas for your group. Enjoy the sunny terrace with panoramic views, an expansive courtyard with a private pool, garden & many lounging spots. -A manual 5seater Car Rental (Cat.B) is included. *This does NOT apply for special offers and not guaranteed for last minute reservations (depends upon agent's availability).

Top 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, 392 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
A private infinity pool reflects clear blue skies, bordered by a spacious terrace. Sun loungers are arranged nearby, offering a view of the mountains and the sea. The landscape features lush greenery and terraced hills, creating a serene outdoor atmosphere.
Cycladic home in Pyrgos Kallistis
4.95 out of 5 average rating, 256 reviews

Andromaches Villa with private pool

Μια πανέμορφη βίλα με παραδοσιακή και μοντέρνα αρχιτεκτονική, στο κέντρο του παραδοσιακού χωριού Πύργος Καλλιστής, με απόλυτη ιδιωτικότητα και ιδιωτικό χώρο στάθμευσης ακριβώς έξω από την βίλα. Μόλις 250μ από την κεντρική πλατεία του χωριού Πύργος, 5χλμ από τα Φηρά, 7χλμ από το διεθνές αεροδρόμιο της Σαντορίνης αεροδρόμιο και 5χλμ. από το λιμάνι. Ευρύχωρο υπνοδωμάτιο, καθιστικό, μπάνιο με ντους, wc, king size κρεβάτι, ιδιωτική βεράντα με καθιστικό και ιδιωτική πισίνα, με θέα στη θάλασσα.

Top guest favorite
An inviting swimming pool is surrounded by a smooth white patio, featuring a unique, modern design that integrates geometric shapes and soft landscaping. Clear turquoise water sparkles in the sunlight, creating a serene atmosphere for relaxation. Sun loungers are positioned nearby for comfort.
Cycladic home in Pyrgos Kallistis
5 out of 5 average rating, 128 reviews

Sunset View Villa, Swimming Pool & Heated Jacuzzi

Newly constructed for your every need, The Bliss Mansion in Pyrgos located in the heart of an historically preserved traditional neighborhood, perched high overlooking Santorini's dramatic landscape and world famous Santorini sunset. This property is secluded from the tourist crowds, yet a few minutes from the most popular Santorini beaches, historical sites, restaurants and bars. The Bliss Mansion can host up to 8 guests, offers a big swimming pool and a luxurious in cave hot tub.

Top guest favorite
An outdoor terrace features a stone structure with a wooden roof, providing shade over a wicker dining table. Sun loungers are positioned near a seasonal swimming pool. The horizon displays soft pastel hues of a sunrise over the sea.
Apartment in Fira
4.98 out of 5 average rating, 187 reviews

Saints Apostles Luxury Villa with private pool

Saints Apostles is a villa divided in two apartments (This listing is for the first floor apartment and the ground floor listing is called "Saints Apostles ") It is located 1,6 klm from Fira town (20 minutes by walking or 2 minutes by car). Is fully luxury furnished , with unlimited sea view to the east side of the island (on the beach side) and the sunrise. Each apartment is private with 2 bedrooms, a kitchen and a living rooms and its own seasonal swimming pool and outside area.

Top guest favorite
A heated mini pool is situated within a cave-style space, illuminated by soft light from surrounding fixtures. An archway frames a view of the sea, with calming turquoise water reflecting the gentle lighting, creating a relaxing environment.
Cycladic home in Fira
4.99 out of 5 average rating, 102 reviews

Revelis Canava

Revelis Canava is a beautiful cave style villa situated right in the center of Fira but still away from the crowed spots. In a spacious and cozy environment you will be able to relax and enjoy the island of Santorini. The terrace, with the lounge area and the heated mini pool, is the ideal spot to watch the spectacular view that the Caldera offers, fantastic sunset colors and relaxing scenery. The second bedroom which is a cave bed as well as the pool are ideal for children.

Top guest favorite
An arched window frames a serene view of the mountains and sea. A private heated jacuzzi and two light-colored bean bags are positioned on the terrace, complemented by potted plants. The natural light enhances the minimalist design of the outdoor space.
Apartment in Pyrgos Kallistis
5 out of 5 average rating, 213 reviews

Star Infinity Suite with private heated Jacuzzi.

Star Santorini Infinity Suites is brand new complex of 3 suites each one with private heated jacuzzi and one shared swimming pool. An exclusive location provides a marvelous seashore&mountain landscape. This Suite is with two bedrooms (one bedroom is loft style bedroom). Two bathrooms,one living area with kitchenette,two balconies,one private jacuzzi and one shared swimming pool. Breakfast (Greek natural products) is provided with extra cost of 15 euro per person per day.

Top guest favorite
A private outdoor veranda features two wooden lounge chairs positioned beside an outdoor plunge pool. Scenic views of the caldera and distant islands are visible, with the serene blue waters stretching towards the horizon.
Cave in Santorini
4.99 out of 5 average rating, 316 reviews

Hector Luxury Cave

Hector Luxury Cave, carved into the unique caldera cliff for more than 250 years was totally renovated during 2016. It is located in the center of the old part of Oia village with breath-taking views over the Caldera cliffs The Hector Luxury Cave is one of the three family owned Cave listings in Oia Village! The three different listings one on top of the other: The Hector Cave House The Hector Luxury Cave The Hector Caldera Nest ΕΣΛ/Licence number: 1167K91000977901

Top guest favorite
A private terrace features a refreshing plunge pool surrounded by whitewashed walls and wooden lounge chairs. Plush pillows are arranged on a nearby seating area, while the iconic blue domes of Oia are visible against the clear sky, overlooking the expansive sea.
Guest suite in Oia
4.98 out of 5 average rating, 221 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 additionally features a private outdoor plunge pool. The view from its terrace is stunning, featuring 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 approximately 23 km.

Top guest favorite
The image captures a private balcony featuring a jacuzzi and outdoor seating arrangement. The horizon displays a tranquil sunset over the Aegean Sea, with gentle waves reflecting vibrant hues. A distant silhouette of an island enhances the serene atmosphere.
Apartment in Imerovigli
4.99 out of 5 average rating, 114 reviews

Artemis Villas ,Caldera View, Imerovigli Santorini

Situated in Magical Imerovigli, nestled amongst traditional white washed settings on the cliffs facing Skaros, 400 meters from sea level offering panoramic, uninterrupted views of the volcanic island that is Megali Kameni, the world famous Caldera and of course the deep blue waters of the Aegean a setting that you will remember for years to come... (please be advised that the hotel is located on the caldera so they may be steps to get to your room and around )

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, 152 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.

Top guest favorite
An infinity pool gently merges with the shimmering caldera below, framed by an elegant archway. The water reflects a tranquil blue, inviting relaxation while offering sweeping views of the volcanic landscape that surrounds.
Cycladic home in Akrotiri
5 out of 5 average rating, 216 reviews

Anemos suite -Private infinity pool & patio

Anemos suite is located in Akrotiri overlooking the caldera and the volcanic islands . It is a suite with Private, Infinity heated Cave style plunge pool with Jet system and private patio. There is a king size bed that can accommodate two person. Daily breakfast is included and served in your suite . There is a cleaning service included. Inform us about your arrival details in advance , we can arrange a taxi/transfer for you.

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