Accommodation with a pool in Santorini caldera

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Top-rated rentals with a pool in Santorini caldera

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Guest favourite

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

28 Jan – 4 Feb

$4,776 AUD total

Guest favourite

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.

1 – 8 Apr

$5,147 AUD total

Guest favourite

Guest suite in Oía

4.98 out of 5 average rating, 150 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 additionally features a private outdoor plunge pool. The view from its terrace is stunning, featuring the caldera and the two iconic blue domes of Oia. Santorini International Airport is about 17 km from Oia Spirit Boutique Residences, and the Ferry Port at approximately 23 km.

29 Apr – 6 May

$7,197 AUD total

Guest favourite

Apartment in Oía

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.

2 – 9 Oct

$6,113 AUD total

Guest favourite

Cycladic home in Pirgos Kallistis

4.94 out of 5 average rating, 175 reviews

Andromaches Villa with private pool

Μια πανέμορφη βίλα με παραδοσιακή και μοντέρνα αρχιτεκτονική, στο κέντρο του παραδοσιακού χωριού Πύργος Καλλιστής, με απόλυτη ιδιωτικότητα και ιδιωτικό χώρο στάθμευσης ακριβώς έξω από την βίλα. Μόλις 250μ από την κεντρική πλατεία του χωριού Πύργος, 5χλμ από τα Φηρά, 7χλμ από το διεθνές αεροδρόμιο της Σαντορίνης αεροδρόμιο και 5χλμ. από το λιμάνι. Ευρύχωρο υπνοδωμάτιο, καθιστικό, μπάνιο με ντους, wc, king size κρεβάτι, ιδιωτική βεράντα με καθιστικό και ιδιωτική πισίνα, με θέα στη θάλασσα.

31 Jan – 7 Feb

$5,147 AUD total

Guest favourite

Home in Mesaria

4.96 out of 5 average rating, 134 reviews

Villa Helena Santorini- Private Plunge Pool & BBQ

Villa Helena is located in a quite neighborhood away from the vast tourist crowds, in the middle of the island at the picturesque settlement of Mesaria. The house is very close to the airport and Fira, the capital. The Villa provides three bedrooms (a master bedroom and a second bedroom which has a loft with the third bedroom). There is also a big living room, fully equipped kitchen, two main bathrooms, a back yard with BBQ and a beautiful terrace with the plunge pool (not heated).

18 – 25 Nov

$1,494 AUD total

Guest favourite

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

31 Oct – 7 Nov

$5,596 AUD total

Guest favourite

Cycladic home in Akrotiri

4.98 out of 5 average rating, 124 reviews

Akrorama - Spilia , private cave pool

Spilia suite by Akrorama is located in Akrotiri overlooking the caldera and the volcanic islands . The suite has Private, Infinity Cave style, heated plunge pool with Jet system. There is a king size bed that can accommodate two person and a sofa bed for extra adult . Daily breakfast is included and served in your suite. Inform us about your arrival details in advance , we can arrange a taxi/transfer for you. Renovated interior 2024 photos coming soon!

6 – 13 Oct

$3,660 AUD total

Guest favourite

Place to stay in Vothonas

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.

13 – 20 Nov

$3,067 AUD total

Guest favourite

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.

14 – 19 Sept

$3,720 AUD total

Guest favourite

Guesthouse in Mesaria

4.9 out of 5 average rating, 286 reviews

Studio with pool view

Our Studio is air-conditioned and consists of one Master bedroom, a dining area with kitchenette, and a bathroom with shower. Outside space includes a terrace with table, sunbeds, umbrella, and immediate access to the pool. TV with Netflix is included.

11 – 18 Feb

$1,067 AUD total

Guest favourite

Apartment in Kamari

4.89 out of 5 average rating, 205 reviews

Deluxe sea view studio

The deluxe sea view studio is a dream come true. Freshly remodeled, with all modern amenities, these rooms are some of the most beautiful in Kamari. Fully equipped kitchenettes, flat screen televisions, ecological air conditioning, renovated bathroom

25 Jan – 1 Feb

$913 AUD total