Vacation rentals with a pool in Islands

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Islands

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

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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, 20 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

A private outdoor heated pool offers a clear view of the sparkling sea and iconic blue-domed churches. The surrounding white architecture is complemented by a bright blue sky and rocky coastline, capturing the essence of Santorini's landscape.

Cycladic home in Oia

4.95 out of 5 average rating, 347 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 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!

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.

Condo in Argyroupoli

4.95 out of 5 average rating, 148 reviews

Modern & Cozy studio with swimming pool

This newly built studio, located in the charming suburb of Argyroupoli in Athens, offers easy access to the public transportation network. Ideal for families, couples, and leisure or business travelers, this studio offers a relaxing and enjoyable stay. The studio features a spacious and comfortable bed, a convertible sofa bed in the living room, a fully equipped kitchen, and a modern bathroom. Guests can also enjoy the outdoor area, which includes a private yard and a shared swimming pool.

Guest favorite

An expansive grassy area features two sun loungers positioned for relaxation, overlooking a serene body of water. In the background, snow-capped mountains rise majestically above the landscape, while a bare tree and a lush green tree add to the natural scenery.

Villa in Pithari

4.93 out of 5 average rating, 124 reviews

Modern house overlooking sea&mountains

Ideal for a couple or a small family.Located in Akrotiri Peninsula,7kms from Chania-Airport and 10 minutes drive from beautiful sandy beaches.Grocery stores and facilities in walking distance.The house is a peacefull and secure residential area amongst small fields.Enclosed property with private parking & BBQ facility.All modern kitchen equipment-Wi-Fi, A/C and garden equipment.Should you wish to hire a car feel free to contact us to get a special offer ! Price includes all applicable taxes.

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.

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, 192 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.

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, 92 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 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

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, 187 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 heated swimming pool is featured, surrounded by a sun terrace. A hanging wicker chair is visible, providing a cozy relaxation spot. Lush greenery borders the area, with sun loungers placed nearby, complemented by a clear blue sky in the background.

Home in Heraklion

5 out of 5 average rating, 124 reviews

Hammam, Private Pool & Home Cinema - Green Sight

**NEW** Private Swimming Pool (3.50mx6.2m) **NEW** Private, Hammam Style, marble Steam Room -inside- the apartment and at guest's disposal! At an ideal location, near the city of Heraklion but way far from city groove, Green Sight Apartment can offer tranquility and a memorable, comfort stay. Enjoy your stay on a modern setting among with an emphatic garden setup with City and Sea Views, only 9km from Heraklion City.

Guest favorite

A panoramic view of the Aegean Sea is captured at sunset, showcasing the horizon where the water meets the sky. Soft pastel hues reflect on the surface of the infinity pool, while distant islands and a lighthouse create a serene landscape.

Cycladic home in Mykonos

4.88 out of 5 average rating, 115 reviews

Adella Studio Mykonos with Pool. Cozy & Charming!

The Cozy & Charming Adella Studio Mykonos is situated at a most beautiful and panoramic location, overlooking the endless blue of the horizon. Spoil yourself in the glorious Greek sun, by the side of the pool, lying between the infinite blue of sea and sky! Enjoy moments of deep relaxation and tranquility, the seascape is one of the most romantic features and invites moments of pure holiday indulgence.