
Holiday 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.

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

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

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.

Artemis Villas ,Caldera View, Imerovigli Santorini
Situated in Magical Imerovigli, nestled amongst traditional white washed settings on the cliffs facing Skaros, 400 meters from sea level offering panoramic, uninterrupted views of the volcanic island that is Megali Kameni, the world famous Caldera and of course the deep blue waters of the Aegean a setting that you will remember for years to come... (please be advised that the hotel is located on the caldera so they may be steps to get to your room and around )

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.

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.

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.

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.

Bluewhite villa with heated private pool
Situated in the traditional village of Pyrgos Kallistis, the heart of Santorini island, my place offers a stunning panoramic view of sunrise and the Aegean Sea. The 130m² Villa features luxury, privacy, easy access and comfort in Cycladic style combined with modern design and decoration. Our new infinity pool is a must! Please note that the pool is functional only for the spring and summer season March 15- October 31st

Deluxe Villa with outdoor Jetted Tub & Sea View
Villa Paride is the luxury honeymoon suite, with private balcony and breath taking caldera-volcano view! Can accommodate till 2 persons. Totally renovated on 2019, with king size bed, new fully equipped kitchen, new bathroom with shower. Balcony with breath taking ocean-caldera-volcano view! Terrace with sun chairs, outdoor private heated pool / jet tube, umbrellas. FREE fast WI-FI

Michelangelo Beach Villa with Sea View
Michelangelo Beach Villa is a perfect getaway destination for those seeking contact with nature and peace of mind. The villa is decorated in respect to the island's tradition, in pastel colors so our guests can take in as much of nature's and sea's beauty as they can. The fresh water hydromassage is not operating during December, January and February.

Serra Exclusive Suites
Our newly-built suites are providing a modern and luxury setting with the best view of the entire Caldera of Santorini (the cliffs, the volcano, Oia, Fira, etc.) where our guests will be pampered and feel like home thanks to the famous Greek hospitality. You can explore an unparalleled travel experience you would not miss for the world.
Popular amenities for Oia rentals with a pool
House rentals with a pool

LyMaRou Collection Suite 6, Pool & Private Hot Tub

Artium Villa with Outdoor Pool hosted by K&K

AROMA CAVAS Suite with caldera view

Santorini's Rising Sun Private Villa

Le Grand Blue Villa with Private Pool & Sea View

Villa Helena Santorini- Private Plunge Pool & BBQ

Luxury Villa, Private Pool, Aegean Sea View

M&D Stories Santorini
Apartment rentals with a pool

Family Maisonette Sea-Sunset Suite Outdoor Jacuzzi

L&E Two Bedroom apartment with jacuzzi

Akrotiri Santorini Two bedroom apartment & pool

Karpimo Suites, Samarina House

Junior Suite Hot Tub Garden View "Baxedes"

Blue Apartment Eos Villa Imerovigli

Ground Floor Room 30 meters from Perissa Beach

Offer!!! Cave Pool Villa
Other holiday rentals with a pool

Little Rock Villa-Oia. Entire Cave House Oia

Aristos Life Luxury Cave Villa 2

Veneston Suites, Lina.

Suite with Pool | Rose

Lioyerma Windmill Villa With Outdoor Hot Tub

Deluxe Suite | Heated Cave Pool | Private Patio

Casa paradiso private villas

Exclusive Villa with Outdoor Heated Pool
When is the best time to visit Oia?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $502 SGD | $499 SGD | $461 SGD | $438 SGD | $459 SGD | $484 SGD | $542 SGD | $492 SGD | $503 SGD | $399 SGD | $397 SGD | $517 SGD |
| Avg. temp | 12°C | 12°C | 14°C | 17°C | 22°C | 27°C | 30°C | 30°C | 26°C | 22°C | 17°C | 14°C |
Quick stats about holiday rentals with a pool in Oia

Total holiday rentals
Explore 200 holiday rentals in Oia

Nightly prices starting at
Oia holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 5,920 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
200 of Oia holiday 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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- Agios Georgios Beach
- Aghia Anna beach
- Plaka beach
- Anafi
- Temple of Demeter
- Mikri Vigla Beach
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- Santa Maria
- Schoinoussa
- Kolympethres Beach
- Alyko Beach
- Museum Of Prehistoric Thira
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- Amoudi Bay
- Akrotiri
- Castle of Sifnos
- Perívolos
- Hawaii Beach
- Three Bells Of Fira
- Cedar Forest Of Alyko
- Ancient Thera
- Temple of Apollon, Portara
- Nisí Síkinos






