This renovated captain's house in Oia, Santorini, enjoys a prime location steps from the caldera and shops. The two-bedroom, two-bathroom property sleeps six guests and boasts a private plunge pool (open April 1st to October 30th), fully equipped kitchen, and stunning caldera views from private terraces.
9.1 70 reviews
Oia
06/27 – 07/04
HK$2310/nighttotal: HK$16170 (7 )
Anemos Caldera Oia
1 2
apartment , Santorini
Anemos Caldera Oia apartment is situated in Oia, Santorini, a short walk from Katharos Beach and approximately 18 kilometres from Santorini (Thira) Airport. This one-bedroom apartment offers a private terrace with stunning sea views, free Wi-Fi, air conditioning, and a private bathroom, sleeping up to two guests and including amenities such as a kettle and safety deposit box.
9.4 84 reviews
Oia
08/30 – 09/01
HK$1320/nighttotal: HK$2640 (2 )
Alsaki Suite By K&k
1 2
apartment , Santorini
Alsaki Suite, a private apartment in Oia, Santorini, is situated steps from the caldera and Oia's town centre, offering easy access to shops, restaurants, and the bus station. This one-bedroom, one-bathroom suite sleeps up to three guests and features air conditioning, a fridge, and excellent user ratings for cleanliness and location; it lacks a terrace or direct caldera view.
9.5 413 reviews
Oia
07/28 – 08/01
HK$3144/nighttotal: HK$12576 (4 )
Helianthus Dream Homes
1 2
apartment , Santorini
The Helianthus Suites- Caldera Caves are located in Oia, a short walk from the famous sunset viewpoint, offering stunning views of the caldera and the Aegean Sea. The property has excellent user, location, and cleanliness ratings, making it a great choice for travellers looking for a comfortable and well-maintained stay. The suites are designed in the traditional Cycladic style, with cave-like structures for a unique and authentic Santorini experience. Guests can enjoy a range of amenities, including air conditioning, a kitchen with a fridge, a jacuzzi, a terrace or balcony, a garden, a concierge, parking, and free Wi-Fi.
9.5 103 reviews
Oia
08/04 – 08/06
HK$1559/nighttotal: HK$3118 (2 )
Vivid Caves 2 Bedroom Cavehouse
2 3
apartment , Santorini
This Santorini cavehouse is located in Foinikiá, a village around 2.6 km from Baxedes Beach and 11.6 km from the Archaeological Museum of Thera. The property has received excellent ratings for location, cleanliness, and overall experience. The two-bedroom apartment is 70 square metres and offers a comfortable living space. Guests can enjoy a terrace with views, a garden, and free Wi-Fi, as well as a kitchen with a fridge and air conditioning.
9.9 171 reviews
Oia
06/25 – 06/29
HK$1614/nighttotal: HK$6456 (4 )
Villa Of The 7 Angels (New Listing) Old Winery Transformed To A Cycladic Villa
2 2
house , Santorini
This charming cave dwelling is situated in the peaceful village of Finikia, just a short distance from the bustling town of Oia and the island's capital, Fira. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience. The villa is comprised of two spacious underground caves, offering unique and comfortable living areas. Guests can enjoy a private yard with stunning sea views, a fully equipped kitchen, air conditioning, free Wi-Fi, and a welcome package upon arrival.
9.6 179 reviews
Oia
06/25 – 06/29
HK$750/nighttotal: HK$3000 (4 )
Canava Cave
1 2
troglodyte , Santorini
CANAVA, a unique 200-year-old cave house in Finikia, Santorini, offers stunning sea and sunset views and is a short 1.6km walk from Oia and the caldera. This two-bedroom, one-bathroom dwelling sleeps four, features a kitchenette with fridge and freezer, a garden, parking, and excellent guest reviews; airport transfers are available.
9.8 50 reviews
Oia
06/25 – 06/29
HK$1894/nighttotal: HK$7576 (4 )
Aerie Neoclassical By Thireon
1 2
house , Santorini
This renovated Captain's house is centrally located in Oia's pedestrian village, a short walk from the Oia Nautical Museum and numerous restaurants. The two-bedroom property, sleeping four, boasts a fully equipped kitchen, air conditioning, a private garden with Aegean Sea views, and a bathroom with a walk-in shower; enjoy sunsets from the terrace.
Oia
07/18 – 07/20
HK$3484/nighttotal: HK$6968 (2 )
Comfort 2-bedroom Apartment In Oia
2 4
apartment , Santorini
This Oia flat provides accommodation in Santorini, located a short distance from the Castle of Oia and Ancient Thira, with the Santorini Caldera and Kamari Beach accessible nearby. This two-bedroom property accommodates up to five guests, featuring air conditioning, Wi-Fi, and a living room with a sofa bed, situated within easy reach of Oia's sunset viewpoints.
9.9 74 reviews
Oia
07/05 – 07/11
HK$2999/nighttotal: HK$17994 (6 )
Aroma Cavas Suite With Caldera View And Sunset
1 6
apartment , Santorini
This Santorini villa is situated in Pyrgos village, Santorini's highest village, offering panoramic caldera views and proximity to Pyrgos castle and traditional tavernas, a short distance from the island's beaches and centre. The two-bedroom, two-bathroom property sleeps seven, boasting a private pool, jacuzzi, garden, parking, and access to a family-owned winery with wine tasting, alongside excellent user ratings for cleanliness, location and overall experience.
9.7 535 reviews
Oia
08/08 – 08/12
HK$13561/nighttotal: HK$54244 (4 )
Hara's Houses All-in-one
5 8
house , Santorini
Studio 4, a caldera-edge apartment in Imerovigli village, boasts unobstructed volcano and Aegean Sea views, close to the Skaros rock formations. This self-catering unit features a fully equipped kitchenette, private terrace with built-in seating, a shared pool, daily cleaning, and options for airport transfers; additional apartments are available for larger groups.
10 1 review
Oia
08/08 – 08/12
HK$19330/nighttotal: HK$77320 (4 )
Villa Oro - 3bdr Heritage Suites With Jacuzzi
1 8
house , Santorini
Villa Oro, a fully renovated captain's mansion in Oia, Santorini, offers convenient access to the island's iconic caldera views, though precise distances to specific attractions are not provided in the listing. This three-bedroom, three-bathroom property sleeps up to 12 guests and boasts a private heated pool, a garden, jacuzzi, and all bedrooms include en-suite facilities, Nespresso machines, and mini-bars; daily housekeeping and concierge services are included.
Best family friendly Oia holiday rentals
Among the 933 accommodations in Oia, here are the 4 best family friendly rentals
9.6 9 reviews
Oia
07/10 – 07/12
HK$1542/nighttotal: HK$3084 (2 )
Rock Cave House
1 2
house , Santorini
ROCK CAVE HOUSE in Oia, Santorini, is a short walk from the Naval Museum of Oia and Katharos Beach, approximately 14km from the Archaeological Museum of Thera. This 55 square metre cave house sleeps four, boasting a fully equipped kitchen, air conditioning, a private terrace, and free Wi-Fi; explore nearby attractions such as Ancient Thera and Akrotiri.
9.8 9 reviews
Oia
08/23 – 08/30
HK$3013/nighttotal: HK$21091 (7 )
Nykteri Cave | A Terre Cave Villas
2 4
house , Santorini
This Santorini villa, near Oia, is less than 2km from the Oia Blue Dome Church viewpoint and Panagia Platsani Church, and a 15-minute walk from Domaine Sigalas Winery. The 45-square-metre property features two bedrooms, a sofa bed, one bathroom, a private pool, and can accommodate up to five guests, benefiting from complimentary breakfast and a free limo/town car service.
9.2 19 reviews
Oia
06/25 – 06/29
HK$1740/nighttotal: HK$6960 (4 )
Chalaris Armeni Villa
2 2
house , Santorini
Chalaris Armeni Villa is situated in Oia, a short walk from the Naval Museum of Oia and a 2km drive from Katharos Beach, offering a peaceful setting with stunning views. The villa consistently receives excellent ratings for its location, cleanliness, and overall experience. This 2-bedroom villa provides comfortable accommodation for up to 5 guests, spanning 40 square meters. Enjoy a private beach area, a fully equipped kitchen, on-site restaurant, laundry service, and the opportunity to explore nearby hiking trails.
9.8 312 reviews
Oia
08/27 – 09/04
HK$2432/nighttotal: HK$19456 (8 )
Oia Lucky Emerald Residence
2 2
resort , Santorini
This two-bedroom, two-bathroom Captain's house in Oia, Santorini, boasts breathtaking caldera views and is within walking distance of Oia's shops and cafes. The 6-guest property features a spacious interior, a private patio with Aegean Sea and volcano views, air conditioning, a kitchen, and internet access; explore nearby hiking paths and admire the Thirassia island vista.
Best Oia holiday rentals with a pool
Among the 933 accommodations in Oia, here are the 4 best rentals with a pool
9.5 1028 reviews
Oia
08/22 – 08/25
HK$2728/nighttotal: HK$8184 (3 )
Caldera Bliss Cave Villa Oia, Santorini Private Terrace Outdoor Hot Tub Breathtaking Caldera Views Traditional Cave-style Luxury Intimate,
1 1
house , Santorini
This cave dwelling is situated in Oia, a picturesque village on Santorini, just 14 miles from the port and 15 miles from the ancient site of Thera. The property enjoys excellent ratings for location, cleanliness, and overall user experience. This Santorini cave villa offers a unique and authentic experience. You'll find a fully equipped kitchen, a private hot tub, and a terrace with stunning sea views. The villa is also close to beaches, restaurants, and local attractions, making it a perfect base for exploring the island.
Oia
07/28 – 08/01
HK$2710/nighttotal: HK$10840 (4 )
Luxury Santorini Villa Villa Elysian Tessera Private Pool 1 Bedroom
1 2
house , Santorini
Villa Elysian Tessera, a luxury Santorini villa in Foinikiá, is situated approximately 9km from Santorini Airport (JTR) and 8.8km from the Archaeological Museum of Fira, offering easy access to Oia and nearby beaches. This one-bedroom, one-bathroom property boasts a private pool with sea views, a fully equipped kitchen, air conditioning, Wi-Fi, and a terrace; guests can enjoy cycling nearby and explore attractions such as Ancient Thera and Akrotiri, both within a 20km radius.
9.9 395 reviews
Oia
07/10 – 07/12
HK$9763/nighttotal: HK$19526 (2 )
Island Blue, Postcard Perfect View & Private Pool
1 2
house , Santorini
This cave house is located in the most famous part of Santorini Island, just a short walk from the main caldera path and the famous blue domed churches. It has received excellent ratings for its location, cleanliness, and overall experience. The property features two bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a private heated pool, a fully equipped kitchen, daily maid and pool service, and a welcome basket with local treats.
9.6 429 reviews
Oia
08/31 – 09/03
HK$5142/nighttotal: HK$15426 (3 )
Super Luxury Santorini Villa Mansion Kyani Private Pool
2 5
house , Santorini
This villa is located in Megalochori, a village on Santorini, just 1.8 km from Thermis Beach and a short drive from Santorini Port and Airport. The property features a private pool, a beautiful terrace, two bedrooms, a dining area, a fully equipped kitchen, and a bathroom, accommodating up to four guests.
Frequently asked questions about holiday rentals in Oia
What are some interesting places to visit in or near Oia?
Oia is a beautiful village, so you'll want to spend time exploring the narrow streets and white-washed houses. Of course, you can't miss the iconic sunset from the caldera. If you want to explore more, you can take a boat trip to the nearby volcanic island of Nea Kameni or Palea Kameni, or visit the ancient Akrotiri archaeological site, which is just a short drive away.
What are the best Airbnb and vacation rentals in Oia?
Which walking or cycling routes are the best in Oia?
The best walking route in Oia is along the caldera edge, from the main village down to Ammoudi Bay. It's about a 30-minute walk, and you'll get stunning views of the Aegean Sea. For cycling, you can explore the back roads around Oia, which are quieter and offer a different perspective on the island. There's a great cycle route that goes all the way to Fira, the capital of Santorini.
What sports or outdoor activites can visitors enjoy in and around Oia?
Oia is perfect for swimming, sunbathing and watersports like paddleboarding and kayaking. You can also go on a boat trip to explore the volcanic islands, or hike to the top of the volcano for incredible views. If you're looking for something more adventurous, you can try rock climbing or scuba diving.
What are the best vacation rentals with a pool in Oia?
What other towns or cities can be easily accessed from Oia?
Oia is well-connected to other towns and cities on Santorini. You can easily take the bus to Fira, the capital, or to Imerovigli, which is another beautiful village on the caldera. From Fira, you can also take a bus to other parts of the island, like Perissa and Perivolos.
What are the best rentals for families and kids in Oia?
What amenities are commonly available in vacation rentals in Oia?
Most vacation rentals in Oia offer basic amenities like a kitchen, bathroom, and Wi-Fi. Many also have balconies or terraces with views of the caldera. You can often find rentals with swimming pools, especially in the more luxurious properties.
What are the best rentals or Airbnbs with a jacuzzi in Oia?
What time of year is best to rent a vacation rental Oia?
The best time to visit Oia is during the shoulder seasons, from April to May and September to October. The weather is still pleasant, but the crowds are smaller and prices are lower. If you want to experience the famous Oia sunset, you'll need to book your accommodation well in advance, especially during peak season.
What are the local dishes in Oia region?
Santorini is known for its delicious cuisine, and Oia has plenty of restaurants serving traditional dishes. Some of the local specialities include fava, a chickpea spread, tomatokeftedes, tomato fritters, and avgolemono, a chicken and lemon soup. You should also try the local wines, which are produced from the Assyrtiko grape.
This Santorini villa offers a prime location, situated just 720 metres from the Santorini Caldera and the Oia Church viewpoint, providing convenient access to major attractions. This two-bedroom apartment features a private swimming pool, a terrace with garden furniture, complimentary Wi-Fi, and on-site parking, accommodating up to five guests with a concierge service available.
9.4 1241 reviews
Oia
06/25 – 06/27
HK$1429/nighttotal: HK$2858 (2 )
Lotza Studios
1 2
studio , Santorini
Lotza Studios are situated in the traditional village of Finikia, a short 15-minute walk from the famous village of Oia, offering a peaceful escape from the crowds. These apartments have consistently received excellent ratings for location, cleanliness, and overall experience. The studios are equipped with a kitchen, a private balcony or shared terrace, and a swimming pool with hydromassage jets. Guests can enjoy a complimentary breakfast, free Wi-Fi, and amenities such as air conditioning, a hairdryer, toiletries, and a flat-screen TV.
9.7 980 reviews
Oia
10/29 – 10/31
HK$2689/nighttotal: HK$5378 (2 )
Morfi Cave House
1 3
apartment , Santorini
Morfi Cave House is located in Oia, a short walk from Katharos Beach and a short drive from the Archaeological Museum of Thera, making it a great choice for exploring the island's beauty. The property has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment offers two bedrooms, a living room, and a well-equipped kitchen, ideal for families or groups of friends. Guests can enjoy amenities such as a private hot tub, a terrace with sea views, free Wi-Fi, and a complimentary welcome drink.
9.8 156 reviews
Oia
06/27 – 07/04
HK$1805/nighttotal: HK$12635 (7 )
Casa Di Magi
1 2
apartment , Santorini
Casa di Magi is a centrally located Fira apartment, conveniently situated near the Archaeological Museum of Thera, Megaro Gyzi, and the Museum of Prehistoric Thera, approximately 6km from Santorini (Thira) International Airport. This one-bedroom, one-bathroom flat offers guests a private terrace with sea and garden views, a swimming pool, tennis court, free Wi-Fi, airport transfers, and on-site parking – a rare find in Fira – alongside a kitchenette and air conditioning.
Best Oia holiday rentals with parking
9.7 779 reviews
Oia
08/04 – 08/06
HK$2394/nighttotal: HK$4788 (2 )
Micasa
2 3
apartment , Santorini
MiCasa is situated in Oia, a charming village known for its stunning sunsets and white-washed houses, just 22.5 kilometres from Santorini Port and Ancient Thera. This apartment has received excellent ratings for its location, cleanliness and overall user experience. This one-bedroom apartment comfortably accommodates two guests and features a kitchen with a fridge and microwave oven, air conditioning, and a terrace. Guests can enjoy a private bathroom, free Wi-Fi, and a paid airport shuttle service, making it an ideal choice for a relaxing and comfortable stay in Santorini.
Oia
08/08 – 08/12
HK$3769/nighttotal: HK$15076 (4 )
Santorini Grace Villa No1
4 8
house , Santorini
This terraced villa is located in the PORI beach area of Imerovigli, Santorini, offering direct sea views and private beach access via a ladder from the balcony, with Fira town just 3 kilometres away and a bus stop 10 metres from the property. This two-floor, 120 square metre dwelling accommodates up to 8 guests, featuring independent floors ideal for two families, a private 5000 square metre land with seasonal produce, a 4.5 x 10 metre infinity swimming pool, air conditioning, Wi-Fi, and facilities for fishing.
Oia
08/08 – 08/12
HK$19828/nighttotal: HK$79312 (4 )
Villa ∙ 3 Bedrooms ∙ 8 Guests
3 8
house , Santorini
Villa Heliades, a luxurious villa in Imerovigli, Santorini, offers panoramic Aegean Sea, mountain, and garden views from its elevated position above the caldera. This family-friendly property accommodates up to eight guests across three bedrooms and three bathrooms, featuring a private swimming pool, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, and parking, situated a short drive from Fira and close to scenic walking paths and sunset viewpoints.
9.9 203 reviews
Oia
06/25 – 06/28
HK$924/nighttotal: HK$2772 (3 )
Thealos Santorini
1 2
apartment , Santorini
Thealos Santorini apartments in Pyrgos offer a family-friendly stay, conveniently located 5km from Santorini Airport, 5.1km from Santorini's port, and 6.6km from the Archaeological Museum of Thera. This self-catering property features a private garden, sun terrace, jacuzzi, and free Wi-Fi, plus breakfast service and car rental options for exploring the island.