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 private terrace features a spacious infinity pool alongside a separate heated plunge pool. Comfortable lounge chairs are positioned by the pool, and a shaded dining area is visible under a modern pergola. Clear views of the sea and distant landscapes are offered.

Villa in Pyrgos Kallistis

4.99 out of 5 average rating, 112 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

A heated plunge pool is situated on a terrace with a scenic arch framing views of the caldera and ocean. The pool features colorful mosaic tiles, while a refreshing beverage can be seen resting on the ledge beside it.

Villa in Imerovigli

4.99 out of 5 average rating, 140 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

The image displays a serene outdoor plunge pool, featuring smooth white archways and clear blue water. Natural light highlights the curves of the structure, creating a tranquil environment. The steps on one side lead into the inviting water, promoting relaxation.

Guest suite in Oia

4.98 out of 5 average rating, 194 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 Boutique Residences, and the Ferry Port at approximately 23 km.

Top guest favorite

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.

Cycladic home in Pyrgos Kallistis

4.95 out of 5 average rating, 187 reviews

Delilah Villa with outdoor swimming pool

H Delilah Villa μπορεί να φιλοξενήσει 5 άτομα, έχει 2 κρεβατοκάμαρες με διπλό κρεβάτι, και ένα καναπέ στο σαλόνι. Έχει ιδιαίτερη διακόσμηση και ένα μεγάλο μπάνιο με ντουζιέρα. Η βεράντα του είναι πολύ μεγάλη με υπέροχη θέα, ιδιωτική πισίνα, καθιστικό και ξαπλώστρες. Ακριβώς μπροστά στη βίλλα υπάρχει ιδιωτικό πάρκινγκ . Ήσυχη γειτονιά με ιδιωτικότητα και υπέροχη θέα. Είναι επίσης πολύ κοντά στη πλατεία του Πύργου , μόλις 200 μέτρα, στην οποία βρίσκονται η αγορά , τα εστιατόρια και τα καφέ.

Guest favorite

Cycladic home in Oia

4.98 out of 5 average rating, 258 reviews

Santorini blue, caldera views, private pool

Traditional Santorini cave house with famous blue dome churches, postcard perfect caldera views in the heart of Oia. next to main path.. Private plunge heated pool with panoramic views. Next to Island blue, Serenity &Eternity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities Other villas : Island blue, Eternity,Serenity,Captains blue, Secret garden, Sailing &Sky blue Flexible on pandemic related cancellations!

Top guest favorite

A private outdoor plunge pool is set against a backdrop of smooth white walls, featuring rounded architectural elements. A door with a blue frame leads into the accommodation, complemented by a small lantern positioned on the pool deck, providing a serene atmosphere.

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

Apartment in Pyrgos Kallistis

5 out of 5 average rating, 147 reviews

Star Infinity Suite with Private heated Jacuzzi

The 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. The complex is constructed in an excuisite Cycladic style and covered with a minimalistic luxury. Natural stone and organic elements create a nobel cosiness. All the furniture and decor is made in authentic Greek style with exclusive and unique elements.

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, 131 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 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, 188 reviews

Akrorama Anemos - Private Pool & Caldera View

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.

Guest favorite

A private indoor cave pool is set within a smooth, naturally formed alcove, with gentle lighting reflecting off the water’s surface. A staircase is visible in the background, leading to a brightly lit area, enhancing the cave's unique ambiance.

Place to stay in Vothonas

4.96 out of 5 average rating, 249 reviews

Mystagoge Retreat with subterranean pool/jacuzzi

Mystagoge Retreat is a unique traditional house, which can accommodate up to two people. A private heated indoor cave pool with jacuzzi will be waiting for you to offer a mystic experience. A light breakfast basket with rusks, jam, honey, tea coffee, milk and butter. Amenities included are WI-FI, air-conditioning, in all areas of house, free parking, sun filled traditional yard with sunbeds, dining area and shared BBQ.

Guest favorite

An upper balcony features a private hot tub alongside a jetted plunge pool, both overlooking a serene landscape. A panoramic view includes the sea and distant islands, with soft hues of twilight casting a tranquil ambiance.

Cave in Fira

4.94 out of 5 average rating, 105 reviews

Villa Cloud, Heated private pool, Caldera view

This exceptional villa is 75 Sq.m, originally built inside volcanic soil has now been reconstructed with a luxurious contemporary futuristic twist. This unique property with its innovative space and surreal construction is embodied with sound motion and visual essence. The villa comprises of a fully equipped kitchen and dining/lounge area which overlooks an intoxicating volcanic view, and peaceful mesmerising sea view.

Guest favorite

A private swimming pool is framed by modern architecture, with comfortable lounging areas and a dining table nearby. Soft lighting enhances the serene outdoor setting. The backdrop features a gently sloping hillside, under a dusky sky transitioning to evening.

Cycladic home in Megalochori

4.88 out of 5 average rating, 115 reviews

Luxury Villa with Private Pool & Great View

Located in an undoubtedly prominent position over the charming caldera, our villas warmly welcome those seeking for personalized luxury holidays in Santorini. Nestled in the famous vineyards of the island, this brand-new complex of suites with private swimming pools is designed with care and respect to the unique landscape. Our luxurious suites are guaranteed to meet and exceed all of your expectations.