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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Guest favorite

Cycladic home in Oia

4.95 out of 5 average rating, 292 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

Jan 28 – Feb 4

R7,977 ZAR per night

Guest favorite

Home in Messinia

4.94 out of 5 average rating, 80 reviews

Cosy Stylish Studio, Kalathi Home Suites in Verga

A private getaway in style. It is situated above the east shore of the Messinian bay, 200 metres above sea level with exquisite 180 degree sea views. A new, contemporary stone property built on half an acre in amphitheatrical style along the Taygetos range. The entire structure is designed with respect to the local traditional architecture. The dwelling is set in a vicinity sparsely-populated, surrounded by olive groves and unique Mediterranean flora. It is part of larger compound of four units

Sep 1 – 8

R1,964 ZAR per night

Guest favorite

Guest suite in Oía

4.98 out of 5 average rating, 150 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.

Nov 6 – 13

R8,130 ZAR per night

Guest favorite

Villa in Venio Daskalio

4.98 out of 5 average rating, 48 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.

Jan 31 – Feb 7

R10,945 ZAR per night

Guest favorite

Home in Lavrion

4.87 out of 5 average rating, 191 reviews

Cape Villa and Sounio

Cape Villa is a stunning, sunlit contemporary house right by the sea. It is perfectly placed to enjoy a relaxed vacation just by the sea, or to combine it with sightseeing around Athens. The house is located on the edge of the cape, just only 20 meters from the sea. It is about 35 minutes drive from Athens airport and about 50 minutes away from Athens city center. The center of Lavrion is only a 5 minute drive and there you can find many tavernas, coffee shops, super markets and bars.

Dec 26 – Jan 2

R6,613 ZAR per night

Guest favorite

Condo in Argiroupoli

4.95 out of 5 average rating, 119 reviews

Modern & Cozy studio with swimming pool

This is a newly built studio located in a suburb of Athens named Argyroupoli. Public transportation network is easily reached. It is ideal for families, couples, travellers (business or/and pleasure) looking to relax and enjoy the accommodation. It includes one large and comfortable bed , a convertible sofa bed at the living room, a fully equipped kitchen and a bathroom. Our guests would also have access in the outdoor area which includes a private yard and shared swimming pool

Dec 6 – 13

R2,816 ZAR per night

Guest favorite

Cave in Santorini

4.99 out of 5 average rating, 253 reviews

Hector Luxury Cave

Hector Luxury Cave, carved into the unique caldera cliff for more than 250 years was totally renovated during 2016. It is located in the center of the old part of Oia village with breath-taking views over the Caldera cliffs The Hector Luxury Cave is one of the three family owned Cave listings in Oia Village! The three different listings one on top of the other: The Hector Cave House The Hector Luxury Cave The Hector Caldera Nest ΕΣΛ/Licence number: 1167K91000977901

Apr 15 – 22

R14,064 ZAR per night

Guest favorite

Cottage in Kythira

4.99 out of 5 average rating, 74 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.

Apr 2 – 9

R2,387 ZAR per night

Guest favorite

Apartment in Corinthia

4.95 out of 5 average rating, 73 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.

Feb 10 – 17

R8,996 ZAR per night

Superhost

Cottage in Neapoli Vion

4.84 out of 5 average rating, 99 reviews

Little Paradise

Welcome to Little Paradise! Our guest house is located in Mesochori, one of the oldest villages of southern Peloponesse where tradition is still alive and time is irrelevant. It's a place of serenity where you can relax, get inspired and meditate The sounds of nature, the ocean and the views, the accommodation, the natural pool, the tree house - it's all here to make you feel like you have a second home where you truly belong

Mar 26 – Apr 2

R1,826 ZAR per night

Guest favorite

Home in Panagia

4.87 out of 5 average rating, 139 reviews

Villa, breathtaking view, pool

In Palaia Epidavros, villa with swimming pool, 2 minutes from the beach and 5 minutes from the village. The apartment includes a big living room, fully equipped kitchen, two bedrooms and two bathrooms. The large private terrace overlooks the sea and the 12-meter swimming pool in the outside living and BBQ area. The apartment is available all year round. Full refurbishment in 2024 - all pictures not yet updated.

Oct 28 – Nov 4

R3,298 ZAR per night

Superhost

Villa in Porto Cheli

5.0 out of 5 average rating, 12 reviews

Villa Artemis in Small Kounoupi Porto Heli

Villa Artemis is located in Agios Emilianos, the most desirable and exclusive area of Porto Heli. It is a luxurious villa surrounded by a beautiful wooded and landscaped garden. The villa has a wonderful view of the sea opposite Spetses Island with a direct and private access to the beach.

Jan 15 – 22

R18,187 ZAR per night