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Holiday rentals with a pool in Regional Unit of Islands

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Top-rated rentals with a pool in Regional Unit of Islands

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Top guest favourite
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, 387 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 favourite
A charming stone villa is presented with a well-maintained lawn in the foreground. Two umbrellas shade lounge chairs, positioned beside a sparkling outdoor pool. The structure features large windows, allowing natural light to brighten the interior. Nearby, a gazebo adds to the outdoor relaxation space.
Villa in Kontopoula
4.99 out of 5 average rating, 114 reviews

Villa Merina Heated Pool

Η Villa Merina βρίσκεται στο Γερολάκκο Κεραμειών σε απόσταση 15χλμ, 20 λεπτά περίπου με το αυτοκίνητο από την πόλη των Χανίων και 35χλμ. απ' το Διεθνές Αεροδρόμιο. Προσφέρει κήπο με εξωτερική πισίνα, βεράντα και εγκαταστάσεις Barbeque. Στις εγκαταστάσεις λειτουργεί δωρεάν ιδιωτικός χώρος στάθμευσης. Η κουζίνα είναι εξοπλισμένη με φούρνο, ηλεκτρικές εστίες μαγειρέματος και ψυγείο. Επίσης, σε όλους τους χώρου παρέχεται δωρεάν wi-fi. Η Villa Merina περιλαμβάνει πετσέτες και κλινοσκεπάσματα.

Top guest favourite
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
4.99 out of 5 average rating, 214 reviews

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.

Top guest favourite
A charming stone cottage sits against a backdrop of rolling hills and the sea, with a gently illuminated sky at dusk. Rustic wooden furnishings are arranged on a terrace, adorned with potted plants, offering stunning views of the landscape.
Cottage in Kythira
4.99 out of 5 average rating, 103 reviews

The Byzantine Chapel Kythira

The BYZANTINE CHAPEL COTTAGE is a truly romantic hideaway. Enjoy complete and total privacy with exceptional sea views and starry nights from your private terrace. LGBTQ+ friendly, clothing optional, and secluded; the chapel is self-contained: comprising a lounge, equipped kitchen (+espresso machine); Shower/WC suite and a mezzanine bedroom. It has its own private access. Experience a perfect night's sleep, wrapped in luxurious bedlinen on a good quality mattress.

Guest favourite
A shaded outdoor lounge area is highlighted by a wooden pergola, providing a view of the sea and coastline. Two loungers face a tranquil pool, while a red sofa with cushions offers additional seating. Surrounding stone walls enhance the secluded atmosphere.
Home in Naxos
4.81 out of 5 average rating, 165 reviews

Villa Katerina

Villa Katerina is a double floor house 62sq.At the first floor there is one living room with kitchen and two single beds .at the second floor there is one bedroom and one big bathroom.There is one big yard 100sq two balconies.The house has amazing sea view from all the floors .It can accommodate up to 4 persons.Also we have barque and hammock.The distance from the sea is 200 meters and the beaches is Placa beach Orkos beach and Mikrivigla Beach

Guest favourite
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
4.97 out of 5 average rating, 149 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 favourite
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.

Top guest favourite
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, 271 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.

Superhost
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
4.95 out of 5 average rating, 113 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.

Top guest favourite
A private infinity pool glimmers under the clear sky, surrounded by loungers and built-in seating. Lush greenery frames the space, with unobstructed views of the Cretan Sea and distant hills beyond. The tranquil setting invites relaxation and offers a seamless connection to nature.
Flat in Chania
5 out of 5 average rating, 105 reviews

Lux Apartment in the Pines with stunning sea view.

Welcome to Kyanon House and Apartment, a scenic, luxurious 2-bedroom, 2- bath apartment with private infinity pool and hydro massage and stunning views of the Cretan sea and town of Chania. Only minutes away from City center and area beaches. Guests of all backgrounds are welcome, this apartment is ideal for couples, and families year round who want to vacation in luxurious comfort and privacy.

Top guest favourite
An illuminated cave pool is surrounded by smooth curves of stone walls, highlighting the modern design. The warm water reflects soft blue tones, creating a serene ambiance in the space. An indirect light source enhances the unique features of the pool area.
Cycladic home in Pyrgos Kallistis
4.96 out of 5 average rating, 285 reviews

Santorini Mayia Cave House with Private Cave Pool

Discover the real Santorini, beyond the crowded touristic routes. Mayia Cave House is a renovated 19th century traditional cycladic cave house in the quiet medieval village of Pyrgos. Offers all modern amenities, a spectacular private large warmed cave pool, a private hot tub in the terrace and incredible views over Santorini, including the famous sunset.

Guest favourite
A private heated plunge pool is featured on a balcony, with two glasses of wine positioned on the edge. The backdrop presents a view of the Acropolis, set against a colorful sky during sunset.
Flat in Athens
4.98 out of 5 average rating, 320 reviews

Acropolis view penthouse w/ heated plunge pool

A unique Acropolis view penthouse, located 1 minute walk from Plaka. Our plunge pool is private & heated, and can be used throughout the year. Smart TV in both bedrooms/ Nespresso coffee maker / AC in all rooms/ Fast Wifi 2 king size bedrooms, 1 king size sofa bed & 2 full bathrooms *** No Parties /events of any kind are allowed ***

Popular amenities for Regional Unit of Islands rentals with a pool

Quick stats about holiday rentals with a pool in Regional Unit of Islands

  • Total holiday rentals

    Explore 1,650 holiday rentals in Regional Unit of Islands

  • Verified guest reviews

    Over 32,800 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,160 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 440 rentals that welcome pets

  • Rentals with dedicated workspaces

    710 properties have a dedicated workspace

  • Wifi availability

    1,630 of Regional Unit of Islands holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Regional Unit of Islands rentals

  • 4.8 Average rating

    Regional Unit of Islands stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    Regional Unit of Islands’s top spots include Acropolis, Plaka and Acropolis Museum

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