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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

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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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, 373 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 spacious terrace features a hot tub and seating area, overlooking a serene ocean view during sunset. The landscape includes a pool and sun loungers, framed by tranquil greenery and the distant shoreline.
Apartment in Stavros
4.97 out of 5 average rating, 121 reviews

Seafront Junior Villa with private heated Jacuzzi

Οι βίλες Vlamis αποτελούνται από 4 παρακείμενα διαμερίσματα και ένα ξεχωριστά, την Junior Villa. Η βίλα ανακαινίστηκε το 2023. Ο σχεδιασμός βασίζεται σε καθαρές γεωμετρίες και φυσικά υλικά σε ανοιχτούς τόνους. Χρησιμοποιήθηκαν υλικά όπως το ξύλο και το ύφασμα, σε συνδυασμό με τεχνοτροπίες σε παστέλ τόνους, για να δημιουργήσουμε ένα φιλόξενο και ηρεμο περιβάλλον για τους επισκέπτες. Έμφαση δόθηκε στη μελέτη του φωτισμού προκειμένου να συνδυαστούν διαφορετικές ποιότητες φωτισμού μέσα στη μέρα.

Guest favourite
Two glasses of sunset cocktails are placed on a small wooden table beside a reclining chair. A vibrant sunset casts warm hues across the sky and reflects on the calm sea, creating a serene backdrop. A distant island is visible on the horizon.
Villa in Mikri Vigla
4.95 out of 5 average rating, 107 reviews

Naxea Villas I

A state-of-the-art 3-bedroom villa, sited on the scenic hill of Orkos, with a private pool, a stunning sea view and a breathtaking sunset view that stays with you forever. Thanks to their prime location, Naxea Villas wondrously combine the calmness of the Aegean with the refreshing power of the island's mountainous scenery, offering a magical destination for families, couples, groups and digital nomads, and an opportunity to experience Naxos at the epitome of comfort, luxury, and authenticity.

Top Guest favourite
A bright outdoor view highlights the villa's modern design, featuring large glass doors that open to a spacious terrace. The private pool reflects the blue sky, while shaded areas with lounge chairs and an umbrella provide relaxation options. Nearby, greenery and hammocks enhance the tranquil atmosphere.
Villa in Platanias
5 out of 5 average rating, 134 reviews

Villa San Pietro - walking distance to everything!

Villa San Pietro is approved by Greek Tourism Organisation & managed by "etouri vacation rental management" San Pietro is a beautiful one-ground-floor Villa, decorated in a lovely vintage style, equipped with quality appliances & furnishings. It is conveniently located within walking distance from the long sandy beach and the centre of the Platanias area, offering you a chance for a car-free & carefree holiday! The villa accommodates up to four guests — two in beds and two on the sofa bed.

Top Guest favourite
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, 218 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 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.

Top Guest favourite
An outdoor dining area features a long table set with plates and glasses. A natural stone structure provides shade, adorned with decorative shells. In the background, the sun sets over the sea, casting a warm glow on the surrounding greenery.
Cycladic home in Imerovigli
4.96 out of 5 average rating, 251 reviews

Sea Horizon

The time has come for me to make my own paradise available to you. Sea Horizon is the new ideal getaway for romantic holidays. Unique seaview, breathtaking sunrises! Reflecting the traditional Cycladic architecture, the villa provides the utmost in privacy and comfort. Feel like home and relax in the private swimming pool! Welcome basket with fruits and wine! We love making our guests happy! Celebrate your special occasion with us and enjoy a complimentary cake!

Top Guest favourite
A stone wall frames a serene outdoor area featuring a dark pool. The water reflects the subtle colors of the sky at dusk, while distant mountains rise above a tranquil landscape. Soft lighting along the wall enhances the peaceful atmosphere.
Villa in Milos
5 out of 5 average rating, 107 reviews

Valeria's House

Traditional Cycladic cave - villa made of wood and stone. Panoramic view of Adamas and the port. Large openings allow light to pass unhindered into the space and act as a tableau vivant on the theme of the natural environment. At 40 sq.m. of the interior are included: bedroom, fully equipped kitchen, living room and bathroom. The outdoor area has a swimming pool. Complete privacy, peace and quiet. Central location, 4 minutes from the port and 7 from the airport.

Top Guest favourite
A clear view of the plunge pool is presented, featuring pristine water reflecting sunlight. The rugged stone exterior of the mansion can be seen in the background, with wooden windows that add warmth to the tranquil setting.
Cottage in Kissamos
4.99 out of 5 average rating, 117 reviews

Harmony Hill House, with unique view and a pool!

LIVE IN HARMONY! Light and space...High ceilings... Wood and stone... Breathtaking sea-mountain views… A stone pool... All so close to magical beaches! This is what I call harmony! This traditional, fully renovated stoned flat mansion of 130 sqm and extra large yard could be your cool 'nest' after wandering around, because you deserve to calm, relax, enjoy and collect lifetime memories. Suitable for 5 people, with two extra roomy bedrooms.

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

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.

Top Guest favourite
A charming stone villa is enveloped by lush green ivy, standing beside a tranquil private swimming pool. The deep blue door contrasts with the warm stone exterior. Tropical plants and vibrant greenery are seen throughout the surrounding area, enhancing the villa's serene atmosphere.
Cottage in Chania
4.98 out of 5 average rating, 129 reviews

★ONLY FOR 2★, COSY STONE VILLA PRIVATE POOL WiFi

Villa 'Sofas' is the perfect romantic holiday haven. Open the wooden picket gate and step into the delightful stone paved courtyard, set behind the stone wall. The villa is built in warm honeyed limestone, and the old wooden shutters and ivy combine to create a wonderful building, full of character. Surrounded by mature shrubs, lush foliage and stone patios, it is easy to imagine you have stepped back in time.

Top Guest favourite
A stone-built villa stands elegantly against a twilight sky, reflecting calm waters of the swimming pool. Warm lights illuminate the structure, emphasizing its architectural features. Outdoor seating is visible, complementing the tranquil atmosphere created by the surrounding landscape.
Villa in Koroni
4.99 out of 5 average rating, 160 reviews

Gerakada Exclusive-Seaview Villa with Private Pool

This stunning stone-built villa offers a private pool for ultimate relaxation and is conveniently located near local beaches, restaurants, and amenities such as supermarkets, bars, and taverns. Zaga beach and Agia Triada are located on 6min away! Guests can enjoy free WiFi and parking. It's an exceptional choice for a memorable and relaxing vacation.

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 1,700 holiday rentals in Regional Unit of Islands

  • Verified guest reviews

    Over 33,060 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,190 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 440 rentals that welcome pets

  • Rentals with dedicated workspaces

    730 properties have a dedicated workspace

  • Wi-Fi availability

    1,680 of Regional Unit of Islands holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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 Parthenon

Destinations to explore