Vacation rentals with a pool in Aegean Islands

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Top-rated rentals with a pool in Aegean Islands

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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

€ 418 per night

Guest favorite

Villa in Imerovigli, Santorini, Thira, Cyclades, Greece

4.98 out of 5 average rating, 106 reviews

Ventus Paradiso Villa, Outdoor Heated Plunge Pool

Our cave villa comes with sentimental value as it belonged to our grandmother. Dated back to 1920's brings a great heritage. The villa was totally renovated in 2015, transforming a traditional cave into a luxury residence following faithfully the unique cycladic architecture with exceptional modern esthetics. The villa consists of two bedrooms with ensuite bathrooms, a dining area and a small kitchenette. It features a heated plunge pool and an upper terrace with panoramic view over Caldera.

Mar 29 – Apr 5

€ 450 per night

Guest favorite

Apartment in Mikonos

4.98 out of 5 average rating, 115 reviews

Sunset Villa w. Infinity Pool near Beach and Town

This new property stands at the top of the hill, overlooking Agios Giannis beach. It sleeps up to 4 guests. The outdoor area is very large and private The breathtaking infinity pool with sunbeds has an amazing view of the Aegean Sea and the island of Delos. While laying on the sunbeds, you have the feeling that the pool and the sea are one, as the sea starts where the pool ends and it provides the most amazing sunset views you will ever see in your life Read the Reviews for more information

Sep 4 – 11

€ 583 per night

Guest favorite

Guest suite in Oía, Greece

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

€ 410 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

€ 708 per night

Guest favorite

Home in Míkonos

4.92 out of 5 average rating, 107 reviews

Mykonos Perla Town House- Pool & Parking, Serviced

Renovated in 2023 and supremely located on a small hilltop, over the town’s sea-front square, the town house offers the luxury of being less than a minute’s walk away from the center of Mykonos, yet enjoying the benefits of privacy, of a shared pool and of private parking. House cleaning is every 3 days and every two days during July & August. The compound is designed by the most celebrated and internationally recognized architect in Greece. Area = 75m2.

Apr 26 – May 3

€ 360 per night

Guest favorite

Cycladic home in Akrotiri

4.98 out of 5 average rating, 124 reviews

Akrorama - Spilia , private cave pool

Spilia suite by Akrorama is located in Akrotiri overlooking the caldera and the volcanic islands . The suite has Private, Infinity Cave style, heated plunge pool with Jet system. There is a king size bed that can accommodate two person and a sofa bed for extra adult . Daily breakfast is included and served in your suite. Inform us about your arrival details in advance , we can arrange a taxi/transfer for you. Renovated interior 2024 photos coming soon!

Oct 6 – 13

€ 320 per night

Guest favorite

Place to stay in Vothonas

4.96 out of 5 average rating, 189 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.

Apr 6 – 13

€ 586 per night

Guest favorite

Villa in Margarites

5.0 out of 5 average rating, 25 reviews

Sunshine Villa - Fairytale countryside villa!

Sunshine Villa has been distinguished with the 2024 Tourism Awards Gold for Mountain Villa of the Year Perched on an elevated location, overlooking the picturesque countryside, Sunshine Villa exudes luxury, romance and fairy tale charm. Surrounded by lush greenery, the villa offers a serene and peaceful environment to unwind and recharge, while gazing at the sea and horizon afar.

Mar 2 – 9

€ 250 per night

Guest favorite

Cycladic home in Oia

4.99 out of 5 average rating, 147 reviews

By the Mill, Caldera, Oia

100 sq meters of traditional cave house - 3 bedrooms and 3 bathrooms, spread over 3 levels of 100 square meters of private terraces and private plunge pool. At Oia's heart - incredible volcano, caldera & sunset views all year round. Easy access, and remarkable privacy, as well as daily housekeeping and plunge pool maintenance.... By the Mill is your dream Santorini home!

Nov 3 – 10

€ 668 per night

Guest favorite

Villa in Mykonos

5.0 out of 5 average rating, 57 reviews

Mykonos Sea View Luxury villa -pool-kite surf-yoga

Calypso Sunset Villa is built in the most privileged position offering complete tranquility combined with breathtaking views and the best sunsets of the island. The villa comprises exquisite luxury, built with every amenity making life richer, more relaxing and more rewarding.

Nov 14 – 21

€ 714 per night

Guest favorite

Apartment in Mykonos

4.95 out of 5 average rating, 131 reviews

Biatriza’s Summer Shelter 1

Lounge in the mottled shade of a pergola and gaze out to where an azure sky meets the Aegean Sea. Prepare meals in a modernized kitchen and dine on a spacious terrace. The cool, relaxing interior is decorated in soft greys and muted earth tones.

Oct 25 – Nov 1

€ 121 per night