Family-friendly holiday rentals in Southern Aegean

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Top-rated family-friendly rentals in Southern Aegean

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Cycladic home in Milos

4.94 out of 5 average rating, 244 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!

30 Oct – 6 Nov

$326 SGD per night

Guest favourite

Cycladic home in Oia

4.95 out of 5 average rating, 291 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

23–30 Oct

$1,166 SGD per night

Guest favourite

Cycladic home in Oia

4.97 out of 5 average rating, 257 reviews

Historic cave house, the old bakery by Cycladica

The old bakery of the village awaits just two minutes from Oia's central square, with a private entrance right on top of the stairs that lead to Armeni bay. Carved in the mountain with respect to the unique local architecture and in harmony with the sun-filled, wild volcanic beauty, the newly restored cave house recounts stories of tradition, heritage and style. The red pumice stones, antique marble floors and handcrafted wooden furniture, create the feeling of an authentic warm hospitality.

22–29 Mar

$714 SGD per night

Guest favourite

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 .

26 Apr – 3 May

$976 SGD per night

Guest favourite

Villa in Imerovigli, Santorini, Thira, Cyclades

4.98 out of 5 average rating, 105 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.

16–23 Feb

$656 SGD per night

Guest favourite

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

23–30 Aug

$1,157 SGD per night

Guest favourite

Cycladic home in Oía

4.95 out of 5 average rating, 199 reviews

Bluedome Suite by Otium Villas & Suites

This is a newly renovated cavehouse that dates back to the 1890's. Situated in one of the most famous neighbourhood's in Oia "Monastiraki" next to the famous St Spyridon Bluedomes. It has been renovated keeping traditional cycladic cavehouse architecture at the forefront of the design while utilising modern building materials. This suite is ideal for couples and families. Its' minimal designed spaces inspire relaxation and comfort for the modern traveller.

20–27 Mar

$481 SGD per night

Superhost

Serviced apartment in Thira

4.88 out of 5 average rating, 101 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.

6–13 Aug

$749 SGD per night

Guest favourite

Cycladic home in Oia

4.83 out of 5 average rating, 226 reviews

Big Blue villa with Hot Tub and Sea View in Oia

Discover unparalleled luxury at our villa in Oia, Santorini. With breathtaking views of the caldera and impeccable design, our spacious accommodations offer a perfect blend of comfort and elegance. Enjoy a private hot tub, attentive hospitality from our dedicated staff, and the convenience of being located in the heart of Oia. Experience the epitome of relaxation and indulgence in this stunning retreat.

15–22 Nov

$615 SGD per night

Guest favourite

Cave in Oia

4.96 out of 5 average rating, 107 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.

23–30 Oct

$632 SGD per night

Guest favourite

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.

24–31 Aug

$772 SGD per night

Guest favourite

Cave in Santorini

4.94 out of 5 average rating, 180 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.

23–30 Nov

$620 SGD per night