Family-friendly vacation rentals in Southern Aegean

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Top-rated family-friendly rentals in Southern Aegean

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Guest favorite

Cycladic home in Milos

4.94 out of 5 average rating, 245 reviews

The Cove | Beach House (Upper)

Escape to serenity with the soothing sounds of waves and the elegant ballet of boats, a legacy crafted by our family's mariner ancestors in the late 19th century. Nestled less than 10 steps from the water, the house rests in perfect harmony with nature and provides an ideal spot to unwind and relax. Eco-friendly and freshly renovated in 2022. What sets us apart is our commitment to annual maintenance, ensuring a perpetually refreshed haven. Explore the timeless allure of coastal living with us!

Oct 31 – Nov 7

R4,221 ZAR per night

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

R7,970 ZAR per night

Guest favorite

Home in Oia

4.95 out of 5 average rating, 276 reviews

GeorgOIA HOUSE-VOLCANO VIEW

My place is close to public transport and the city center. My place is good for couples, solo adventurers, business travelers, and families (with kids). This House has 2 bedrooms with double beds ,a third bedroom with 2 single beds ,2 private shower rooms , a fully equipped kitchen ,a living room with a sofa bed and a big private veranda with perfect view to the sea ,the caldera ,the volcano and the traditional village of OIA. There is also a big Jacuzzi faces the Volcano and caldera cliff .

Nov 25 – Dec 2

R12,938 ZAR 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.

Mar 29 – Apr 5

R8,957 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

Aug 23 – 30

R15,804 ZAR per night

Superhost

Apartment in Thira

4.88 out of 5 average rating, 102 reviews

Superior Suite with Outdoor Hot Tub & Caldera View

Superior Suite is located in the complex of Exclusive Plan Suites in Firostefani Santorini and it is an Adults only accommodation.The breathtaking view of sparkling waters of the Aegean sea and the azur sky of Cyclades Islands is ideal for relaxing holidays in luxury. The suite also faces the amazing Caldera View offering the finest panoramic sunset view. Located close enough to the center but far enough from the crowdy places of the island.

Nov 1 – 8

R5,573 ZAR per night

Guest favorite

Cave in Oia

4.96 out of 5 average rating, 109 reviews

Angle Cave House with Jacuzzi and Sunset View

An amazing suite, that respects the traditional architecture of Santorini, with a breathtaking view of Caldera and the famous sunset of Oia. Literally hanging over the cliffs of Oia overviewing Ammoudi Bay, which lies within walking distance. The accommodation is a spectacular location, however there are few steps to get there, nothing too demanding for someone who is an abled walker.

Oct 23 – 30

R8,637 ZAR per night

Guest favorite

Cycladic home in Oia

4.85 out of 5 average rating, 224 reviews

Bluedome Cavehouse by Otium Villas & Suites

This is a traditional cave house that has been newly renovated, situated on the cliffs of Oia. The house is amongst the most privileged, having a stunning view over the caldera, a breathtaking scenery that most have enjoyed only through postcards or advertising imagery. Only a few steps from the main road, right in the heart of Oia. Optional breakfast available with extra charge.

Apr 20 – 27

R13,137 ZAR per night

Guest favorite

Cave in Oia

4.92 out of 5 average rating, 241 reviews

Pano Meria Cave House One in Oia

A unique cave house built into the face of the cliff overlooking the majestic caldera. Private plunge pool and terrace where you can spend the entire day admiring the views. The epitome of slow living in Oia. Fits up to three people and we can add a fold up bed.

Apr 12 – 19

R12,879 ZAR per night

Guest favorite

Cave in Santorini

4.94 out of 5 average rating, 181 reviews

Lava Cave suite 1BR/Private Plunge Pool+Panoramic View

Live the myth by staying in a cave that used to be a sailor's domicile back in 1875. Today after a full restoration, it has been turned into a jewel, keeping its traditional cave-curved Aegean island style with its pearl white walls.

Nov 23 – 30

R8,471 ZAR per night

Guest favorite

Villa in Imerovigli

4.99 out of 5 average rating, 175 reviews

ENTIRE PRIVATE ANTRUM VILLA with Sunset View+Pool

Your one of a kind experience staying at the edge of the world overlooking the Santorini Sunset and Volcano while enjoying your favourite drink in the heated pool. Truly unique and unforgettable experience.

Sep 13 – 20

R18,341 ZAR per night

Guest favorite

Cycladic home in Mykonos

4.98 out of 5 average rating, 103 reviews

Private Suite, Outdoor Hot Tub & Impeccable Views!

Our Private Suite with the Outdoor Hot Tub and the Impeccable Views at La Maison Blanche Mykonos Properties guarantees that you will enjoy the best of Mykonos island, combined with our absolute privacy!

Jul 25 – Aug 1

R9,193 ZAR per night