
Vacation rentals with a pool in Oia
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Oia
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Canava Villas II - Private Pool - Santorini
Villa#2 comes in 2 level floors and accommodates up to 6 people. On the ground floor there is a master bedroom, bathroom, fully equipped kitchen, lounge and WC. The upper floor provides 4 single floor mattresses or 2 double ones & its own bathroom. Outdoor private pool with Jacuzzi, patio, dinning area and sun lounges! Welcome drinks, basket of seasonal products, Nespresso coffee, Concierge services, A/C, Netflix, daily housekeeping, laundry services and many more amenities are waiting for you!

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

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.

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.

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.

The Blue Domes Cave House by Spitia Santorini
Experience the iconic beauty of Santorini at The Blue Domes Cave House, a truly enchanting and luxuriously appointed home perfectly situated in the heart of Oia. Directly facing the world-famous blue domes, offers an unrivalled vantage point for breathtaking caldera views and mesmerising sunsets from its private outdoor plunge pool. Ideal for a romantic escape or a small family, accommodating up to 5 guests, it embodies the magic of Santorini with its unique charm and prime location.

BLUE ART CAVES - Starry Sky Cave with hot-tub
This elegant suite is perched on the cliffs of the caldera in Oia. It combines traditional Cycladic architecture with a minimal decorative style, making it the perfect choice for those who want to relax. The suite features a private indoor hot tub, offering full privacy along with stunning views of the caldera and volcano. Breakfast is included in the price. The room is equipped with air conditioning, free Wi-Fi, coffee and tea-making facilities, bath amenities, and a smart TV.

Cave Villa With Heated Plunge Pool & Caldera View
A traditional cave villa with modern touches that can accomodate up to four people with spacious veranda and breathtaking caldera views. Lathouri Cave Villa is perched on the famous caldera cliffside overlooking the Aegean sea and the two volcanic islands Palia and Nea Kameni. The traditional cycladic architecture along with the unique scenery makes it the perfect choice for those who want to enjoy a relaxing vacation in the lap of luxury.

Hector Cave House
Hector Cave House, carved into the unique caldera cliff for more than 250 years, was originally used as a wine cellar. Then it became a family owned complex of three different properties that opened its doors to share its unique character to travelers from around the world. 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

MyBoZer Twins Odyssey Heated private pool
Our brand new My Bozer twin villas are located by the sea, right at the entrance of the famous Oia village. Villa Iliada and villa Odyssey can host couples, families or group of friends, offering all necessary amenities that will guarantee a relaxed, private holidays in the most beautiful place on earth, Santorini island! You can either book one (up to 6 guests) or both villas (12 guests) if you wish to spend holidays with friends

Akrorama Anemos - Private Pool & Caldera View
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.

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.
Popular amenities for Oia rentals with a pool
House rentals with a pool

Beach front Villa Pasithea @home by the sea

LyMaRou Collection Suite 6, Pool & Private Hot Tub

Artium Villa with Outdoor Pool hosted by K&K

AROMA CAVAS Suite with caldera view

Villa Helena Santorini- Private Plunge Pool & BBQ

Thadeos Villa with jetted pool

Luxury Villa, Private Pool, Aegean Sea View

M&D Stories Santorini
Condo rentals with a pool

Family Maisonette Sea-Sunset Suite Outdoor Jacuzzi

Akrotiri Santorini Two bedroom apartment & pool

Junior Suite Hot Tub Garden View "Baxedes"

Karpimo Suites, Samarina House

Blue Apartment Eos Villa Imerovigli

Ground Floor Room 30 meters from Perissa Beach

Offer!!! Cave Pool Villa

Suite G 7
Other vacation rentals with a pool

Little Rock Villa-Oia. Entire Cave House Oia

Junior Villa CalderaView-Plunge Pool |Nano Canaves

Villa Murat - Caldera view apartment

Santorini Sky | The Retreat Suite *NEW*

Inspire Santorini Luxury Villas - A2

Santorini Delux

Private Villa with Pool in Oia, view, parking

Abelomilos Luxury by The Sea
Quick stats about vacation rentals with a pool in Oia
Total rentals
200 properties
Nightly prices starting at
R174 ZAR before taxes and fees
Total number of reviews
5.7K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
- Athens Vacation rentals
- Cythera Vacation rentals
- Santorini Vacation rentals
- Mykonos Vacation rentals
- Pyrgos Kallistis Vacation rentals
- Saronic Islands Vacation rentals
- Chalkidiki Vacation rentals
- Rhodes Vacation rentals
- Regional Unit of Islands Vacation rentals
- Evvoías Vacation rentals
- East Attica Regional Unit Vacation rentals
- Thira Vacation rentals
- Rentals with breakfast Oia
- Serviced apartment rentals Oia
- Private suite rentals Oia
- Hotel rentals Oia
- Rentals with a patio Oia
- Bed and breakfasts Oia
- Waterfront rentals Oia
- Pet-friendly rentals Oia
- Fitness-friendly rentals Oia
- Smoking-friendly rentals Oia
- Rentals with outdoor seating Oia
- Rentals with beach access Oia
- Villa rentals Oia
- Cycladic house rentals Oia
- Family-friendly rentals Oia
- Rentals with a washer and dryer Oia
- House rentals Oia
- Boutique hotel rentals Oia
- Cave rentals Oia
- Rentals with a hot tub Oia
- Apartment rentals Oia
- Rentals with pools Greece
- Firostefani
- Agios Georgios Beach
- Aghia Anna beach
- Aghios Prokopios beach
- Schoinoussa
- Livadia Beach
- Magganari Beach
- Anafi
- Plaka beach
- Logaras
- Grotta Beach
- Maragkas Beach
- Golden Beach, Paros
- Nisí Síkinos
- Mikri Vigla Beach
- Temple of Demeter
- Aqua Paros - Water Park
- Anafi Port
- Santa Maria
- Manalis
- Kolympethres Beach
- Pyrgaki Beach
- Hatzidakis Winery / Οινοποιείο Χατζηδάκη
- Venetsanos Winery