Vacation 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 favorite

A serene swimming pool is surrounded by natural stone tiles and two reclining lounge chairs facing the water. Lush greenery and flowering plants enhance the area, with a partially covered terrace visible in the background.

Tiny home in Islands

5 out of 5 average rating, 23 reviews

Oleander Cottage, pool side, stunning view.

Experience the magic tranquility and seclusion of our rural retreat. Oleander Cottage has been designed with great care to ensure the utmost comfort, whilst enjoying fabulous elevated panoramic sea-views across to the Peloponnese; and magical clear starry nights from your own terrace. LGBTQ+ friendly, and clothing optional. You are private, but have immediate access to the swimming pool with the same wonderful views. The cottage is fully equipped, and self contained with its own private entry

Guest favorite

An outdoor area is highlighted by a private swimming pool, surrounded by greenery and modern fencing. A comfortable seating arrangement consists of a large, cushioned sofa and a small table, creating a relaxing space for guests to enjoy leisure time by the water.

Home in Argyroupoli

4.95 out of 5 average rating, 153 reviews

Modern & Cozy suite with swimming pool

Welcome to the Garden Suite at Urban Serenity Suites – a modern, self-contained space in the peaceful suburb of Argyroupoli, Athens. Just minutes from the metro and with easy access to the city center, airport, and southern coast, this suite is perfect for both business and leisure travelers. Whatever brings you to Athens, you'll enjoy the privacy, style, and comfort of your own private courtyard – ideal for relaxing – along with access to a quiet, semi-private pool just steps from your door.

Top guest favorite

A sparkling swimming pool reflects the clear blue sky, framed by a stone patio with lounge chairs. The two-story villa features an arched balcony and greenery surrounding the property, creating a peaceful atmosphere. Sun loungers are positioned beside the pool, inviting relaxation.

Home in Lagonisi

4.93 out of 5 average rating, 109 reviews

VILLA DRYAS-Pool&seaview private Villa-Lagonissi

Splendid relaxing stay on top of a hill just above the sea. Family holiday in a private, traditional rustic style,2-storey villa of 160 m2 in a 1250 m2 garden with a 40 m2 swimming pool, ponds, bbq and many different options to sit and enjoy the wonderful view. All the facilities are for the exclusive use up to 6 visitors (+1baby) who enjoy to combine the calm and quiet of nature with the vivid options of the coastal front of Attica. Just an hour from center of Athens and 25 min from Airport.

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, 114 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

An expansive rooftop terrace features spacious lounge beds arranged around a radiant infinity pool. Soft lighting illuminates the area, contrasting against the twilight sky that frames the horizon of the sea. A serene atmosphere is created for relaxation and enjoyment of the stunning ocean views.

Apartment in Limenas Chersonisou

4.96 out of 5 average rating, 126 reviews

Seafront Apt. by Myseasight.com Studio Gardenview

Escape to Seafront Suites, a private hideaway beside a celestial blue sea on Hersonissos stunning Beach Rivera. Nestled on a tranquil and secluded bay with panoramic views and sunsets that dazzle, the rest of the world does not exist, giving you freedom to release your inhibitions and live for the moment. More information Our luxury Suite with garden view is modern and minimalist with extremely comfortable guest rooms, earth tones and modern touches to soothe the mind and warm the soul.

Top guest favorite

The outdoor area features a stone terrace overlooking a serene infinity pool, with panoramic views of the sea and the surrounding mountains. Lounge chairs with rolled towels are arranged by the pool's edge, offering a perfect space for relaxation under clear blue skies.

Villa in Venio Daskalio

4.99 out of 5 average rating, 84 reviews

Forecastle

Our beautiful Villa is located in a hidden heaven mounted rock, which is covered by the sea as far as the human eye can see. The rough, authentic beauty of nature is beautifully linked to the superior design and luxury of the building. Our villa will be a pleasant surprise with its minimal design, in absolute respect to the simple lines of nature, with a view to the sun emerging from the mountains of Evia. A small staircase leads to a private rock beach with calming crystal clear waters.

Top guest favorite

An expansive outdoor terrace surrounds a glittering swimming pool, featuring loungers and a shaded seating area. The space offers panoramic views of the sea, with a stone wall adding texture to the minimalist architecture of the villa in the background.

Villa in Kokkino Chorio

5 out of 5 average rating, 16 reviews

Astelia Villa

Welcome to Astelia Villa, a newly built (July 2024), luxurious residence, offering the perfect blend of elegance and tranquility. This exquisite villa boasts a minimalistic design, a private swimming pool, and expansive outdoor terraces with breathtaking panoramic sea views and magical sunsets. Ideally situated between Chania and Rethymno, and just a short distance from stunning beaches, historical landmarks, and natural sights, Astelia Villa is your ultimate getaway in Crete.

Guest favorite

A refreshing swimming pool with clear water is surrounded by natural stone flooring. Two wooden lounge chairs with striped fabric are positioned on the edge, providing a place to relax and enjoy the surrounding landscape. The expansive view of the sea and distant mountains is visible under a bright blue sky.

Cottage in Kythira

4.99 out of 5 average rating, 96 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 favorite

Townhouse in Corinthia

4.96 out of 5 average rating, 91 reviews

Nautilus-Luxury is private seafront in to the blue

A beautiful seafront fully furniched three level NEW house in a relaxing very private location with 2 infinity swimming pools and lounging equipment, offer guests great comfort for their stay. The location is ideal for family or friends to enjoy high quality architecture and astonishing panoramic sea view behind to a quit beach , Here the sea meets the sky and the mountain dives into the sea, a poem without words .Near in Athens, Epidaurus, Nafplio, Mikines.

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, 133 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, 193 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 favorite

A private pool reflects the soft glow of exterior lights, surrounded by a stone terrace. The unique structure features a wooden roof, while large windows allow for indoor views. Comfortable lounge chairs are positioned near the water, creating a serene environment.

Villa in Tinos

5 out of 5 average rating, 28 reviews

Celini villa Tinos

Relax making a unique and peaceful getaway in nature that the area offers you. The Moon is distinguished for its uniqueness, simplicity, luxury and tranquility! The private pool -jacuzzi will fill you with moments of coolness and relaxation!! The pool makes for all seasons (spring-up) as you heat up the water with a heat pump, so you can enjoy it other months outside of Summer! Your vacation will be unforgettable...