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, 293 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

ﺩ.ﺇ1,580 per night

Guest favorite

Villa in Imerovigli, Santorini, Thira, Cyclades

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.

Apr 1 – 8

ﺩ.ﺇ1,776 per night

Guest favorite

Guest suite in Oía

4.96 out of 5 average rating, 126 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 features a private outdoor plunge pool. Its interior is a unique space with a double bed and a living room. It has stunning view to the caldera and the two iconic blue domes of Oia. Santorini International Airport is about 17 km from Oia Spirit, and the Ferry Port at about 23 km.

Nov 22 – 29

ﺩ.ﺇ1,194 per night

Guest favorite

Apartment in Mikonos, Greece

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 5 – 12

ﺩ.ﺇ2,289 per night

Guest favorite

Apartment in Oía, Greece

4.98 out of 5 average rating, 110 reviews

BLUE ART CAVES - Starry Sky

These elegant and fully revovated villas on 2021, are perched on the cliffs of the caldera in Oia. Combines the traditional cycladic architecture with minimal decorative style makes them the perfect choice for those who want to relax. Each of the suites has a private indoor hottub with sea views. Breakfast included in the price and delivered at the accommodation. Rooms are air conditioned and offer free wifi in all areas, coffee and tea making facilities , bath amenities and satellite TV.

Oct 2 – 9

ﺩ.ﺇ2,109 per night

Guest favorite

Cave in Santorini

4.99 out of 5 average rating, 254 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

Oct 31 – Nov 7

ﺩ.ﺇ1,925 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 29 – May 6

ﺩ.ﺇ1,439 per night

Guest favorite

Cave in Thira, Greece

5.0 out of 5 average rating, 69 reviews

Cave Villa With Heated Plunge Pool & Caldera View

A traditional cave villa with modern touches that can accomodate up to four people with spacious veranda and breathtaking caldera views. Lathouri Cave Villa is perched on the famous caldera cliffside overlooking the Aegean sea and the two volcanic islands Palia and Nea Kameni. The traditional cycladic architecture along with the unique scenery makes it the perfect choice for those who want to enjoy a relaxing vacation in the lap of luxury.

Nov 6 – 13

ﺩ.ﺇ1,542 per night

Guest favorite

Place to stay in Vothonas, Greece

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.

Nov 24 – Dec 1

ﺩ.ﺇ1,002 per night

Guest favorite

Villa in Urla, Turkey

5.0 out of 5 average rating, 30 reviews

Villa where you will find your heart surrounded by nature

Come and experience this peaceful experience with your friends or family in a free Aegean villa nestled in nature with fruit trees on 12 acres of land in Urla Kekliktepe. To make your beautiful moments more enjoyable, you can go to the center of Urla at a moment and have a pleasant time. You can visit popular spots, vineyards, seaside and chat in the peaceful atmosphere of your home in nature again.

Nov 29 – Dec 6

ﺩ.ﺇ1,851 per night

Guest favorite

Cycladic home in Oia, Greece

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!

Mar 31 – Apr 7

ﺩ.ﺇ2,948 per night

Guest favorite

Villa in Mykonos, Greece

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

ﺩ.ﺇ2,677 per night