
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

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.

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.

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.

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

Sunset Cave House by Spitia Santorini
Embrace the quintessential Santorini experience at the Sunset Cave House, a magical retreat carved into the volcanic rock of Oia's caldera cliff. This traditional yet luxuriously appointed accommodation offers unparalleled panoramic views of the Aegean Sea and the world-famous Oia sunset from your private outdoor plunge pool. Accommodating up to 3 guests, it promises an intimate and unforgettable stay where every moment is bathed in the island's unique light.

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.

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.

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

New Earth Home-View & Outdoor Refreshing Whirlpool

Christa's home

Triple garden view(3)

LyMaRou Collection Suite 6, Pool & Private Hot Tub

AROMA CAVAS Suite with caldera view

Le Grand Blue Villa with Private Pool & Sea View

Villa Helena Santorini- Private Plunge Pool & BBQ

Luxury Villa, Private Pool, Aegean Sea View
Condo 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

Offer!!! Cave Pool Villa

Suite G 7
Other holiday rentals with a pool

Little Rock Villa-Oia. Entire Cave House Oia

Santorini Sky | The Retreat Suite *NEW*

Romantic private pool suite oasis!

Ardor-Superior Villa with private pool

Exclusive Villa with Outdoor Heated Pool

Inspire Santorini Luxury Villas - A2

Studio Santorini Twin/Double

Christina's Villa
When is the best time to visit Oia?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $707 NZD | $704 NZD | $650 NZD | $618 NZD | $647 NZD | $682 NZD | $764 NZD | $693 NZD | $709 NZD | $583 NZD | $592 NZD | $652 NZD |
| 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 $18 NZD per night before taxes and fees

Verified guest reviews
Over 5,670 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
200 of Oia holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Oia rentals

4.9 Average rating
Oia stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Cythera Holiday rentals
- Athens Holiday rentals
- Santorini Holiday rentals
- Pyrgos Kallistis Holiday rentals
- Saronic Islands Holiday rentals
- Mykonos Holiday rentals
- Regional Unit of Islands Holiday rentals
- Evvoías Holiday rentals
- Rhodes Holiday rentals
- East Attica Regional Unit Holiday rentals
- Chalkidiki Holiday rentals
- Thira Holiday rentals
- House rentals Oia
- Rentals with a hot tub Oia
- Boutique hotels Oia
- Pet-friendly rentals Oia
- Rentals with a patio Oia
- Family-friendly rentals Oia
- Serviced apartment rentals Oia
- Rentals with breakfast Oia
- Villa rentals Oia
- Smoking-friendly rentals Oia
- Fitness-friendly rentals Oia
- Bed and breakfasts Oia
- Rentals with outdoor seating Oia
- Rentals with a washing machine and dryer Oia
- Hotel rooms Oia
- Waterfront rentals Oia
- Cycladic house rentals Oia
- Cave rentals Oia
- Apartment rentals Oia
- Private suite rentals Oia
- Rentals with beach access Oia
- Rentals with pools Greece
- Agios Georgios Beach
- Aghia Anna beach
- Livadia Beach
- Magganari Beach
- Plaka beach
- Logaras
- Grotta Beach
- Maragkas Beach
- Mikri Vigla Beach
- Temple of Demeter
- Aqua Paros - Water Park
- Anafi Port
- Santa Maria
- Schoinoussa
- Kolympethres Beach
- Manalis
- Golden Beach, Paros
- Pyrgaki Beach
- Perivolos
- Moraitis winery
- Agiassos Beach
- Venetsanos Winery
- Παραλία Μυλοπότας
- Alyko Beach






