Family-friendly vacation rentals in Pyrgos Kallistis

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Top-rated family-friendly rentals in Pyrgos Kallistis

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Guest favourite

Cycladic homes 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. 24 – 31

$183 CAD per night

Guest favourite

Cycladic homes in Milos

4.94 out of 5 average rating, 246 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

$434 CAD per night

Guest favourite

Cycladic homes 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

$621 CAD per night

Guest favourite

Villa in Milos

4.97 out of 5 average rating, 183 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. 21 – 28

$99 CAD 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 .

Jan. 22 – 29

$957 CAD per night

Guest favourite

Cycladic homes 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.

Jan. 26 – Feb. 2

$217 CAD per night

Guest favourite

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.

Nov. 28 – Dec. 5

$153 CAD per night

Guest favourite

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.

Apr. 8 – 15

$566 CAD per night

Guest favourite

Cycladic homes 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. 15 – 20

$677 CAD per night

Guest favourite

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. 30 – Dec. 7

$103 CAD per night

Guest favourite

Condo in Porto Cheli

4.95 out of 5 average rating, 129 reviews

Holiday house in unique position

An independent, fully equipped house hosting up to 4, surrounded by a lush Mediterranean garden a few steps from a private stone deck. Ten minutes by car from P.Cheli village, the area offers the opportunity to make many excursions, sea sports or just relax on one of its nice beaches.

Mar. 19 – 26

$213 CAD per night

Guest favourite

Cycladic homes in Paros

4.97 out of 5 average rating, 106 reviews

Magaya Beach House

Situated in a private estate this newly renovated Cycladic house is only a few steps away from the beach. It can sleep up to 5 persons and is fully equipped to provide a relaxing holiday escape. Within walking distance from main town. (AMA00000215672)

Apr. 16 – 23

$178 CAD per night