Family-friendly vacation rentals in Pyrgos Kallistis

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Top-rated family-friendly rentals in Pyrgos Kallistis

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Guest favorite

Cycladic home in Pyrgos Kallistis

4.99 out of 5 average rating, 215 reviews

Olyra Traditional Cave Houses

The traditional residences Olyra Traditional Houses, are in the heart of the medievial settlement of Pyrgos, very close to the imposing Kasteli (castle). A three minute walk in the stone laid pavements and side strees is enough to go from Olyra to the central parking of the village as well as the central square. Our houses are created in the same place where the bakery of the village was two centuries ago, with great respect and attachment to Santorinis¨ architecture. The decoration is character

Mar 30 – Apr 6

$116 per night

Guest favorite

Cycladic home in Milos

4.94 out of 5 average rating, 243 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 7 – 14

$301 per night

Guest favorite

Cycladic home in Oia

4.95 out of 5 average rating, 290 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

Dec 20 – 27

$374 per night

Guest favorite

Villa in Milos

4.97 out of 5 average rating, 181 reviews

Valeria's Apartment

Private, high-ceilinged farmhouse apartment with bedroom and bathroom. Special kitchen corner, preparation of breakfast & cold dishes. 2 balconies (40m2 in total), with a panoramic view of the port in front and the sea of Sarakiniko behind (the lunar landscape is only 15 minutes away on foot). Distances: 4 minutes from the port and 7 from the airport by car, Plaka: 5km, Pollonia: 7km, Fyriplaka-Tsigrado in 15 minutes. Recently landscaped garden, natural environment with privacy & tranquility

Oct 16 – 23

$67 per night

Guest favorite

Cycladic home in Pyrgos Kallistis

4.91 out of 5 average rating, 179 reviews

House with three terraces overlooking Aegean Sea

Casa Galazia is our beautiful secluded vacation home with a superb view to the Aegean Sea and the mountain of Profitis Ilias. The house offers a spacious living room with a well equipped kitchen, a spectacular bathroom carved out in a rock and on the first floor a bedroom with double bed giving direct access to a lovely balcony. It is nestled against the picturesque village of Pyrgos, home to more than forty churches, winding little alleyways and the remains of a Venetian castle.

Oct 9 – 16

$118 per night

Guest favorite

Cave in Santorini

4.99 out of 5 average rating, 252 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 26 – Nov 2

$611 per night

Guest favorite

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.

Apr 13 – 20

$353 per night

Guest favorite

Cycladic home in Milos

5.0 out of 5 average rating, 188 reviews

Villa Tasoula Sunrise apartment

Villa Tasoula it's located 1km from Adamas downtown ,built with Cycladic architecture it is separated in two floors. Upstairs live my family,at the first floor we made 4 places for hosting. Two apartments and two studio. The Sunrise apartment 45 sq.m. fully equipped available for 3 person.there is not sea view but it is 150 meters from the beach of papikinou, ιdeal for relaxing and pleasant holidays !

Oct 13 – 20

$111 per night

Guest favorite

Guesthouse in Idra

4.96 out of 5 average rating, 166 reviews

Levante

The most famous ship in Hydra island, opens one of it's cabins to accommodate new friends. A window in the Aegean sea, a roof under the stars, where the senses meet every expression of nature, where all encounter the divine, forgotten feelings are born again, where the body rests and the heart is breathing . A retreat created with love to offer love, warmth and uplift of the soul.

Mar 21 – 28

$97 per night

Guest favorite

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.

Oct 23 – 30

$407 per night

Guest favorite

Cycladic home in Pyrgos Kallistis

4.95 out of 5 average rating, 211 reviews

Santorini Mayia Cave House with Private Cave Pool

Discover the real Santorini, beyond the crowded touristic routes. Mayia Cave House is a renovated 19th century traditional cycladic cave house in the quiet medieval village of Pyrgos. Offers all modern amenities, a spectacular private large warmed cave pool, a private hot tub in the terrace and incredible views over Santorini, including the famous sunset.

Sep 13 – 20

$406 per night

Guest favorite

Apartment in Pyrgos Kallistis

4.97 out of 5 average rating, 102 reviews

AROMA CAVAS APARTMENT WITH STONE AND PERFECT VIEW

The stone-built apartments are located in Pyrgos-Santorini, with a spectacular view of Santorini. The apartments have a bedroom with a double bed, a living room with a sofa bed, a bathroom and a courtyard with views of the island. Within 5 minutes there are taverns, mini market, bus stop.

Nov 23 – 30

$64 per night