
Vacation rentals with a pool in Oia
Find and book unique homes with a pool on Airbnb
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 $110 per night before taxes and fees

Verified guest reviews
Over 6,900 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
210 of Oia vacation rentals include wi-fi 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!
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

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.

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.

Home of Lilies
A stylishly designed private villa in harmony with traditional architecture invites you to enjoy your holiday in one of the most beautiful islands in the word. The Home of Lilies is recently built and decorated to high standards. Set in a peaceful rural landscape of vineyards, in an extremely conveniently situated area on the edge of busy Fira's center and 1,7 km from the quiet but organized beach of Exo Gialos. It is an ideal base to explore the island within a short car trip.

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.

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.

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.

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.

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

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.

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.

Lioyerma Windmill Villa With Outdoor Hot Tub
At the edge of the traditional settlement of Oia, overlooking the Caldera and the world-famous Oia sunset, stands our fully renovated traditional Windmill, originally built in 1900. This unique three-level residence is connected by internal staircases and can comfortably accommodate a couple with two children or up to four adults. Breakfast is included, and free parking is available for all guests.
Popular amenities for Oia rentals with a pool
House rentals with a pool

STILVI SUITE

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

Villa Helena Santorini- Private Plunge Pool & BBQ

AROMA CAVAS Suite with caldera view

Latipi House

Villa with Pool and Jacuzzi

Luxury Villa, Private Pool, Aegean Sea View

Santorini's Rising Sun Private Villa
Condo rentals with a pool

Cave House in Karterados Beach

Family Maisonette Sea-Sunset Suite Outdoor Jacuzzi

Junior Suite Hot Tub Garden View "Katharos"

Loukas & Emma "Studio with hot tub"

Karpimo Suites, Samarina House

CAVE SAND PRIVATE HOUSE WITH PRIVATE POOL

Suite G 8

Akrotiri Santorini Two bedroom apartment & pool
Other vacation rentals with a pool

Deluxe Suite with Plunge Pool @Aplada Suites

Saints Apostles Luxury Villa with private pool

The Blue Domes Cave House by Spitia Santorini

Villa Cloud, Heated private pool, Caldera view

Hector Cave House

Casa Luz, Κυκλαδίτικο σπίτι

Abelomilos Luxury by The Sea

Santorini Mayia Cave House with Private Cave Pool
When is the best time to visit Oia?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $419 | $413 | $347 | $272 | $320 | $401 | $429 | $389 | $398 | $316 | $314 | $409 |
| Avg. temp | 54°F | 54°F | 58°F | 63°F | 71°F | 80°F | 85°F | 86°F | 79°F | 72°F | 63°F | 56°F |
Destinations to explore
- Luxury rentals Oia
- Private suite rentals Oia
- Cycladic house rentals Oia
- Rentals with beach access Oia
- Hotel rooms Oia
- Serviced apartment rentals Oia
- Rentals with breakfast Oia
- Cave rentals Oia
- Apartment rentals Oia
- Villa rentals Oia
- Boutique hotels Oia
- Waterfront rentals Oia
- Family-friendly rentals Oia
- Pet-friendly rentals Oia
- Bed and breakfasts Oia
- House rentals Oia
- Rentals with a hot tub Oia
- Rentals with pools Greece
- Schoinoussa
- Anafi
- Agios Georgios Beach
- Aghia Anna beach
- Plaka beach
- Golden Beach, Paros
- Nisí Síkinos
- Santa Maria
- Perívolos
- Mikri Vigla Beach
- Temple of Demeter
- Hawaii Beach
- Kolympethres Beach
- Alyko Beach
- Amoudi Bay
- Temple of Apollon, Portara
- Castle of Sifnos
- Ancient Thera
- Museum Of Prehistoric Thira
- Panagia Ekatontapyliani
- Santo Wines
- Akrotiri
- Three Bells Of Fira
- Aghios Prokopios beach
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes







