Vacation rentals with a pool in Oia

A private heated pool is seen on a terrace, offering unobstructed views of the deep blue sea and distant islands. The scene includes iconic white buildings with blue domes, set against a clear sky, showcasing typical Santorini architecture.

4.95 out of 5 average rating, 413 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

4.84 out of 5 average rating, 109 reviews

Apartment in Oia

Deluxe Suite with Plunge Pool @Aplada Suites

Our property features two similar Deluxe Suites, designed for comfort, privacy, and relaxation. Each villa offers a loft-style bedroom, a fully equipped kitchen, living and dining area, and a Cycladic bathroom. Each villa comes with private plunge pool, ideal for unwinding while enjoying the landscape. While located very close to Oia’s center, they provide a peaceful retreat. Please note that we have two similar suites, and allocation is made randomly by our system at the time of booking.

Guest suite in Pyrgos Kallistis

A private terrace features a tranquil pool surrounded by a smooth, light-colored deck. Cozy, round seating is positioned nearby, offering a view of the expansive blue sea and hills in the distance. A small wooden table holds refreshments, inviting relaxation.

Infinity Pool • Luxury Villa • Sea View

Enjoy breathtaking sunsets and panoramic views of the Caldera, volcano and Aegean Sea from your private pool and terrace. Located in Pyrgos, Vista Dall Alto combines privacy, comfort and easy access to every corner of Santorini. The villa features 2 comfortable bedrooms, 2 modern bathrooms, a fully equipped kitchen and spacious indoor and outdoor living areas. Enjoy complimentary breakfast delivery and daily housekeeping while relaxing by your private pool and enjoying sunset views.

4.96 out of 5 average rating, 203 reviews

4.99 out of 5 average rating, 114 reviews

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 home in Fira

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.

4.97 out of 5 average rating, 119 reviews

A private terrace is showcased, featuring a heated pool surrounded by sun loungers and an outdoor dining area. Blue and white accents are visible in the decor, offering a stunning view of the sea and cliffs beyond. The serene setting emphasizes tranquility.

Cave in Oia

Authentic 2 Bdrm Villa with Plunge Pool & Sea View

Villa Hercules is an authentic 250 year old cave. With the proper renovation it always has the traditional character but all the modern comforts with 2 separate bedrooms. One with a double bed, the other with a king-size bed and 2 single sofa beds. Fully equipped kitchen, WC with shower on the same floor and large bathroom with jacuzzi in the basement. Living room with office corner and dining area. Large private terrace with heated pool, dining area, sunbeds, umbrellas, view.

4.99 out of 5 average rating, 232 reviews

A private terrace features comfortable seating with plush cushions, small wooden table, and decorative bottles. The space provides a clear view of the deep blue ocean and surrounding caldera, complemented by the whitewashed buildings of Oia in the background and a bright blue sky.

Guest suite in Oia

Suite with 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. Right out of a post card between the two iconic blue domes of Oia. This suite has a private terrace with astonishing panoramic view to the caldera and the blue domes. Santorini International Airport is about 17 km from Oia Spirit, and the Ferry Port at approximately 23 km.

4.99 out of 5 average rating, 328 reviews

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

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

Cycladic home in Pyrgos Kallistis

A private infinity pool reflects clear blue skies, bordered by a spacious terrace. Sun loungers are arranged nearby, offering a view of the mountains and the sea. The landscape features lush greenery and terraced hills, creating a serene outdoor atmosphere.

Andromaches Villa with private pool

A beautiful villa with traditional and modern architecture, in the center of the traditional village of Pyrgos Kallisti, with absolute privacy and private parking right outside the villa. Just 250m from the central square of Pyrgos village, 5km from Fira, 7km from Santorini International Airport and 5km from the port. Spacious bedroom, living room, bathroom with shower, toilet, king size bed, private terrace with living room and private pool, overlooking the sea.

4.95 out of 5 average rating, 275 reviews

4.99 out of 5 average rating, 173 reviews

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

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.

4.98 out of 5 average rating, 190 reviews

A modern villa is presented with a distinctive white dome roof, surrounded by greenery and blue sea views. A shaded patio features sun loungers beside a small swimming pool, providing a relaxing outdoor space. The bright blue doors complement the serene landscape.

Dome in Oia

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

A view from the terrace features a custom-built hot tub with clear water, surrounded by whitewashed walls. In the background, a traditional blue-domed church tower stands prominently against a serene sea and sky, capturing the charm of the Oia landscape.

4.96 out of 5 average rating, 256 reviews

Bluedome Suite by Otium Villas Santorini

Luxury Cave Suite in Oia | Private Heated Jacuzzi | Sea & Caldera Views Wake up in a stylish cave suite carved from Santorini’s volcanic cliffs, just steps from Oia’s most iconic blue-domed churches and world-famous sunset spots. Designed for couples or small families who value modern comfort, traditional Cycladic charm, and panoramic views, Bluedome Suite at Otium Villas delivers a tranquil, unforgettable Santorini experience.

4.92 out of 5 average rating, 121 reviews

An upper balcony features a private hot tub alongside a jetted plunge pool, both overlooking a serene landscape. A panoramic view includes the sea and distant islands, with soft hues of twilight casting a tranquil ambiance.

Cave in Santorini

Villa Cloud, Heated private pool, Caldera view

This exceptional villa is 75 Sq.m, originally built inside volcanic soil has now been reconstructed with a luxurious contemporary futuristic twist. This unique property with its innovative space and surreal construction is embodied with sound motion and visual essence. The villa comprises of a fully equipped kitchen and dining/lounge area which overlooks an intoxicating volcanic view, and peaceful mesmerising sea view.

Popular amenities for Oia rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 99 reviews

Home in Santorini

Amaranthine Villa

4.98 out of 5 average rating, 169 reviews

A serene view of an outdoor jacuzzi is presented, surrounded by smooth stones and featuring a clear blue surface reflecting the sky. Beyond the jacuzzi, a scenic view of the hillside and coastline is visible, enhancing the sense of tranquility.

Home in Santorini

Sea view Villa 'Avra' @home by the sea!

4.96 out of 5 average rating, 200 reviews

A terrace features a plunge pool surrounded by tiled surfaces. A suspended chair adds a relaxing touch, with potted flowers bringing a hint of color. The view includes clear blue skies and a glimpse of distant buildings, enhancing the outdoor ambiance.

Home in Mesaria

Villa Helena Santorini- Private Plunge Pool & BBQ

4.88 out of 5 average rating, 168 reviews

An outdoor terrace features a blue-tiled jacuzzi surrounded by glass railings. Two sunbeds are positioned nearby, accompanied by a small table. Clear skies above highlight the serene and inviting space, ideal for relaxation.

Home in Emporeio

Latipi House

4.96 out of 5 average rating, 140 reviews

An outdoor area features a well-maintained pool with a clear blue surface, surrounded by several lounge chairs. Lush greenery and flowering plants are visible, with expansive views of the landscape and the sea beyond, showcasing the beauty of Santorini.

Home in Pyrgos Kallistis

AROMA CAVAS Suite with caldera view

5.0 out of 5 average rating, 4 reviews

Home in Merovígli

Villa with Pool and Jacuzzi

4.97 out of 5 average rating, 37 reviews

A private swimming pool with a sleek design features comfortable loungers positioned alongside. An outdoor seating area is visible under a shaded alcove, with a view of the Aegean Sea in the background. The clear blue sky complements the tranquil setting.

Home in Vourvoulos

Luxury Villa, Private Pool, Aegean Sea View

4.88 out of 5 average rating, 17 reviews

A terrace offers an inviting space with a round dining table surrounded by chairs, complemented by a lounge area. A pool reflects the colorful hues of sunset over the Aegean Sea, and a railing provides an unobstructed view of the landscape.

Home in Vourvoulos

Nostos Exquisite Residence | Pool | Sunrise View

Condo rentals with a pool

4.83 out of 5 average rating, 177 reviews

A rustic kitchen area features wooden cabinetry and a granite countertop. An arched stone entrance leads to a cozy living space, illuminated by warm light. A wooden chair is positioned near the entrance, enhancing the inviting character of the space.

Condo in Karterados

Cave House in Karterados Beach

4.93 out of 5 average rating, 90 reviews

A spacious sleeping area is framed by large open doors, revealing a stunning sunset view. Blue accents in the window frames complement the bright white walls. A cozy seating area with cushions rests alongside the room, enhancing the overall serene atmosphere.

Condo in Merovígli

Family Maisonette Sea-Sunset Suite Outdoor Jacuzzi

4.91 out of 5 average rating, 67 reviews

A comfortable seating area is positioned near a sparkling turquoise swimming pool, surrounded by sunbeds and umbrellas. Lush greenery and colorful flowers can be observed in the background, enhancing the serene atmosphere of the outdoor space.

Condo in Oia

Junior Suite Hot Tub Garden View "Baxedes"

4.55 out of 5 average rating, 38 reviews

A private terrace features a refreshing outdoor jacuzzi beside two lounge chairs and a hanging swing chair. Minimalist white decor is complemented by greenery and subtle shadows cast by the overhead trellis. A small table holds decorative items, creating a space for relaxation.

Condo in Perissa

Loukas & Emma "Studio with hot tub"

An inviting outdoor pool is surrounded by sun loungers and shaded by large umbrellas. A dining area with wooden seating is visible in the background, framed by a stone wall and natural scenery, creating a relaxing outdoor space.

Condo in Exo Gonia

Karpimo Suites, Samarina House

4.87 out of 5 average rating, 191 reviews

A sunlit outdoor area features a clear swimming pool surrounded by lounge chairs and sun umbrellas. The space is framed by olive trees, with a view of distant blue waters and hills under a clear sky.

Condo in Exo Gialos

CAVE SAND PRIVATE HOUSE WITH PRIVATE POOL

4.76 out of 5 average rating, 107 reviews

Condo in Kamari

Suite G 6

5.0 out of 5 average rating, 3 reviews

The outdoor area features a tranquil swimming pool surrounded by lounge chairs under soft lighting, creating a relaxed ambiance. The building presents a mix of traditional architecture and modern design, with multiple windows reflecting the evening light.

Condo in Santorini

Akrotiri Santorini Two bedroom apartment & pool

4.25 out of 5 average rating, 4 reviews

Other vacation rentals with a pool

Villa in Pyrgos Kallistis

Martynou View Villas

4.97 out of 5 average rating, 150 reviews

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.

4.99 out of 5 average rating, 150 reviews

Alonistra Oia Houses - House with private pool

4.95 out of 5 average rating, 254 reviews

A picturesque view from a window showcases a private plunge pool with clear blue water. An umbrella provides shade, while expansive views of the caldera and cliffs create a serene backdrop under a clear sky.

Cave in Oia

The Volcano Cave House by Spitia Santorini

Cycladic home in Akrotiri

An infinity pool gently merges with the shimmering caldera below, framed by an elegant archway. The water reflects a tranquil blue, inviting relaxation while offering sweeping views of the volcanic landscape that surrounds.

Anemos suite -Private infinity pool & patio

5.0 out of 5 average rating, 238 reviews

4.96 out of 5 average rating, 162 reviews

A private pool is featured within a sunlit terrace, surrounded by modern architectural elements. The clear water of the pool reflects the sky, while lounge chairs are positioned nearby for relaxation. The expansive space allows for unobstructed views of the surroundings.

Villa in Akrotiri

Serra | Caldera View Suite, Private Pool & Hot Tub

Place to stay in Vothonas

A private indoor cave pool is set within a smooth, naturally formed alcove, with gentle lighting reflecting off the water’s surface. A staircase is visible in the background, leading to a brightly lit area, enhancing the cave's unique ambiance.

Mystagoge Retreat with subterranean pool/jacuzzi

4.96 out of 5 average rating, 296 reviews

A serene terrace features comfortable seating beside a clear hydromassage pool. The smooth surface of the water reflects the soft colors of the sky, while gentle waves can be seen lapping at the shoreline in the distance.

4.89 out of 5 average rating, 181 reviews

Michelangelo Beach Villa with Sea View