Holiday rentals with a pool in Santorini caldera

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Santorini caldera

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Serviced apartment in Oía

4.99 out of 5 average rating, 134 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.

Guest favourite

Guest suite in Oía

4.98 out of 5 average rating, 172 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.

Guest favourite

Cycladic home in Megalochori

4.98 out of 5 average rating, 123 reviews

Ambeli Sunset Villa/private heated pool

Ambeli sunset villa's unique allocation provides the famous sunset view at the caldera avoiding the overcrowding of the famous cities of Santorini. Trying to provide 5 stars services for our guests, we serve breakfast daily privately inside the villa (included in the rate) as well as the daily cleaning service Additionally, as no facilities are public, Guests are experiencing the use of the pool in maximum privacy while the view from the terrace promises romantic and memorable sunsets.

Guest favourite

Cycladic home in Pirgos Kallistis

4.95 out of 5 average rating, 203 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.

Guest favourite

Home in Mesaria

4.95 out of 5 average rating, 163 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).

Guest favourite

Cycladic home in Oia

4.98 out of 5 average rating, 239 reviews

Santorini blue, caldera views, private pool

Traditional Santorini cave house with famous blue dome churches, postcard perfect caldera views in the heart of Oia. next to main path.. Private plunge heated pool with panoramic views. Next to Island blue, Serenity &Eternity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities Other villas : Island blue, Eternity,Serenity,Captains blue, Secret garden, Sailing &Sky blue Flexible on pandemic related cancellations!

Guest favourite

Cave in Santorini

4.99 out of 5 average rating, 281 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

Guest favourite

Cycladic home in Imerovigli

4.96 out of 5 average rating, 224 reviews

Sea Horizon

The time has come for me to make my own paradise available to you. Sea Horizon is the new ideal getaway for romantic holidays. Unique seaview, breathtaking sunrises! Reflecting the traditional Cycladic architecture, the villa provides the utmost in privacy and comfort. Feel like home and relax in the private swimming pool! Welcome basket with fruits and wine! We love making our guests happy! Celebrate your special occasion with us and enjoy a complimentary cake!

Guest favourite

Cycladic home in Akrotiri

5 out of 5 average rating, 178 reviews

Akrorama - Anemos , private pool

Anemos suite is located in Akrotiri overlooking the caldera and the volcanic islands . It is a suite with Private, Infinity heated Cave style plunge pool with Jet system and private patio. There is a king size bed that can accommodate two person. Daily breakfast is included and served in your suite . There is a cleaning service included. Inform us about your arrival details in advance , we can arrange a taxi/transfer for you.

Guest favourite

Place to stay in Vothonas

4.95 out of 5 average rating, 228 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.

Guest favourite

Rental unit in Fira

4.98 out of 5 average rating, 191 reviews

Saints Apostles Villa with private pool

Saints Apostles is located in a quite area 1,5 klm from Fira town (20 minutes by walking or 2 minutes by car). Is fully luxury furnished , unlimited sea view to the east side of the island (on the beach side) and to the sunrise. The house is divided in 2 villa apartments with each apartment been private with its one swimming pool and all the amenities we describe.

Guest favourite

Cycladic home in Pyrgos Kallistis

4.96 out of 5 average rating, 250 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.