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Vacation rentals with a pool in Oia

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Top-rated rentals with a pool in Oia

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

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Top guest favourite
A heated plunge pool is featured within a uniquely shaped archway, with clear blue water reflecting the sun. A stunning view over the ocean and distant islands is visible through the opening. Decorative cushions and a small table with refreshments enhance the inviting atmosphere.
Villa in Imerovigli
4.99 out of 5 average rating, 161 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.

Top guest favourite
An aerial view showcases a private swimming pool with a unique shape, surrounded by lush palm trees. A sunshade offers a resting area beside the pool, which sparkles under the clear blue sky, enhancing the tranquil environment of the outdoor space.
Cycladic homes in Episkopi Gonias
4.97 out of 5 average rating, 108 reviews

Casa Luz, Cycladic house

Casa Luz is located in Santorini, in the traditional village of Episkopi Gonia, near Pyrgos area. This newly built Cycladic home blends harmoniously with its surroundings, offering expansive views of the Aegean Sea. Sensitively designed and luxuriously appointed, the residence creates a serene atmosphere and provides a refined holiday retreat for those seeking privacy and relaxation. It is 4km from Santorini Airport and 6km from Fira Town, while the black beach of Kamari is 2.5km away

Guest favourite
A private plunge pool is visible in the foreground, reflecting clear blue water. The stunning caldera view features vibrant blue dome churches in the distance, with the Aegean Sea stretching out toward a clear sky. Whitewashed buildings create a serene backdrop.
Cycladic homes in Oia
4.97 out of 5 average rating, 302 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
A heated mini pool is situated within a cave-style space, illuminated by soft light from surrounding fixtures. An archway frames a view of the sea, with calming turquoise water reflecting the gentle lighting, creating a relaxing environment.
Cycladic homes in Fira
4.99 out of 5 average rating, 104 reviews

Revelis Canava

Revelis Canava is a beautiful cave style villa situated right in the center of Fira but still away from the crowed spots. In a spacious and cozy environment you will be able to relax and enjoy the island of Santorini. The terrace, with the lounge area and the heated mini pool, is the ideal spot to watch the spectacular view that the Caldera offers, fantastic sunset colors and relaxing scenery. The second bedroom which is a cave bed as well as the pool are ideal for children.

Top guest favourite
An arched window frames a serene view of the mountains and sea. A private heated jacuzzi and two light-colored bean bags are positioned on the terrace, complemented by potted plants. The natural light enhances the minimalist design of the outdoor space.
Apartment in Pyrgos Kallistis
5 out of 5 average rating, 215 reviews

Star Infinity Suite with private heated Jacuzzi.

Star Santorini Infinity Suites is brand new complex of 3 suites each one with private heated jacuzzi and one shared swimming pool. An exclusive location provides a marvelous seashore&mountain landscape. This Suite is with two bedrooms (one bedroom is loft style bedroom). Two bathrooms,one living area with kitchenette,two balconies,one private jacuzzi and one shared swimming pool. Breakfast (Greek natural products) is provided with extra cost of 15 euro per person per day.

Top guest favourite
A private outdoor veranda features two wooden lounge chairs positioned beside an outdoor plunge pool. Scenic views of the caldera and distant islands are visible, with the serene blue waters stretching towards the horizon.
Cave in Santorini
4.99 out of 5 average rating, 320 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

Top guest favourite
A private terrace features a refreshing plunge pool surrounded by whitewashed walls and wooden lounge chairs. Plush pillows are arranged on a nearby seating area, while the iconic blue domes of Oia are visible against the clear sky, overlooking the expansive sea.
Guest suite in Oia
4.98 out of 5 average rating, 224 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, and the Ferry Port at approximately 23 km.

Top guest favourite
A private terrace offers a view of the shimmering Aegean Sea, framed by the surrounding caldera cliffs. A plunge pool in inviting turquoise reflects the clear sky. Two elegant flutes stand beside a bowl of fresh fruit, inviting relaxation and enjoyment.
Cave in Oia
4.99 out of 5 average rating, 154 reviews

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.

Top guest favourite
A private non-heated splash pool is positioned on a terrace with a view of the ocean and distant hills. Surrounding the pool, decorative stones and a straw hat add a relaxed touch to the inviting space. Bright sunlight reflects off the water's surface.
Cycladic homes in Oia
4.99 out of 5 average rating, 134 reviews

Alonistra Oia Houses - House with private pool

Our brand new luxury traditional apartment in Alonistra Oia Houses, with non-heated splash pool is built and decorated according to the traditional style of the island with taste and elegance,relaxing colours and romantic details.Is situated in a tranquil and pleasant location in Finikia village, only 15 minutes walk from the main pedestrian of Oia. It has one king size double bed on the ground floor and one single bed in the upper floor.

Guest favourite
An infinity pool with crystal-clear water reflects the serene sky, framed by a curved architectural feature. The pool seamlessly blends into the view of the caldera and volcanic islands, providing a tranquil setting for relaxation.
Cycladic homes in Akrotiri
5 out of 5 average rating, 218 reviews

Anemos suite -Private infinity pool & patio

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.

Top guest favourite
Cycladic homes in Oia
4.99 out of 5 average rating, 198 reviews

By the Mill, Caldera, Oia

100 sq meters of traditional cave house - 3 bedrooms and 3 bathrooms, spread over 3 levels of 100 square meters of private terraces and private plunge pool. At Oia's heart - incredible volcano, caldera & sunset views all year round. Easy access, and remarkable privacy, as well as daily housekeeping and plunge pool maintenance.... By the Mill is your dream Santorini home!

Top guest favourite
An illuminated cave pool is surrounded by smooth curves of stone walls, highlighting the modern design. The warm water reflects soft blue tones, creating a serene ambiance in the space. An indirect light source enhances the unique features of the pool area.
Cycladic homes in Pyrgos Kallistis
4.96 out of 5 average rating, 286 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.

Popular amenities for Oia rentals with a pool

When is the best time to visit Oia?

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Quick stats about vacation rentals with a pool in Oia

  • Total vacation rentals

    Explore 210 vacation rentals in Oia

  • Nightly prices starting at

    Oia vacation rentals start at $138 CAD per night before taxes and fees

  • Verified guest reviews

    Over 5,670 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    210 of Oia vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oia rentals

  • 4.9 Average rating

    Oia stays are highly rated by guests—averaging 4.9 out of 5!

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