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Authentic 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly

Photo gallery for Authentic 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly

A poolside area with two lounge chairs, a view of the sea, and white buildings in the background.
A dining area with a checkered tablecloth, wooden chairs, and a view of the sea through an open door.
A hillside village with white buildings, terraced streets, and outdoor seating areas.
A white-washed hillside village with terraced houses, outdoor seating, and a pool.
A kitchen with blue cabinets, a stainless steel range hood, a hanging pot rack, and a window with blue shutters.

Reviews

10 out of 10
Exceptional

Highlights

  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Discover nearby landmarks
    Walk to Santorini Caldera
2 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Massages in spa
  • Patio
  • Spa pool on site
  • Private pool
  • Breakfast included
  • Kitchenette

Explore the area

View map
Oia, Egeo
  • Place, Santorini Caldera
    ‪1 min walk‬
  • Place, Oia Blue Dome Church Viewpoint
    ‪2 min walk‬
  • Place, Castle of Oia
    ‪6 min walk‬
  • Airport, Thira (JTR-Santorini National)
    ‪29 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

2 Single Beds and 1 Queen Bed

Bedroom 2

1 Double Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Bidet · Toilet · Jetted bathtub

Spaces

Deck or patio
Kitchen
Kitchenette
Garden
Dining area

About this property

Authentic 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly

Villa Hercules is a traditional luxury Santorinian cave house decorated like the original Santorinian houses.

This original/authentic cave-house is very old (about 250 years old).

With the appropriate renovation, this particular cave house is transformed in a very comfortable appartment with all amenities of today, with an absolute respect of local tradition.

There are 2 bedrooms, the original cave room ( sospito) with a double bed , the big bedroom with a king bed and 2 sofa-beds ( piso camara), a living room with dinning table (sala), fully equipped kitchen, wc with shower, and a big bathroom with jet tube downstairs.

The big private terrace, with sunbeds, a private pool overlooking caldera, shower, and dinning corner, is full of flowers, and its a must !!
Free fast WI-FI , free laundry, complimentary champagne, local wine, and more extras !
Free complete breakfast in the villa.

A/C in the living area keeps all villa Fresh. In each bedroom there are silently ceiling fans.
In the heart of Oia, close to everything, but in a very quiet place !

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House Rules

Check in after 3:00 PM
Check out before 11:00 AM
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Children

Adults only
Children ages between 0-11 are not allowed.
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Events

No events allowed
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Pets

Pets allowed
Only very small pets and quiet
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Smoking

Smoking is not permitted
Children ages between 0-11 are not allowed.

Important information

You need to know

Property Registration Number 1167Κ91001326101
Property # 6560220
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Santorini

Located in Santorini, this villa is in the city centre and on the waterfront. Castle of Oia and Ancient Thira are notable landmarks, and the area's natural beauty can be seen at Santorini Caldera and Kamari Beach. Maritime Museum and Lost Atlantis Experience Museum are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with ecotours and hiking/biking trails.
View more Villas in SantoriniOpens in a new window
Map
Oia, Egeo

What's nearby

  • Santorini Caldera - 1 min walk - 0.0 km
  • Oia Blue Dome Church Viewpoint - 2 min walk - 0.2 km
  • Castle of Oia - 6 min walk - 0.5 km
  • Amoudi Bay - 9 min walk - 0.6 km
  • Ammoudi - 13 min walk - 0.9 km

Getting around

  • Thira (JTR-Santorini National) - 20 min drive

Restaurants

  • ‪Lotza - ‬3 min walk
  • ‪Flora - ‬3 min walk
  • ‪Passaggio - ‬8 min walk
  • ‪pitoGyros - ‬4 min walk
  • ‪Santo Souvlaki - ‬3 min walk

Frequently asked questions

Does Authentic 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Authentic 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Authentic 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly?

On-site parking is available at the property.

What time is check-in at Authentic 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly?

Check-in begins at 3:00 PM.

What time is check-out at Authentic 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly?

Checkout is at 11:00 AM.

Where is Authentic 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly located?

Located in the heart of Santorini, this villa is steps away from Oia Blue Dome Church Viewpoint and Santorini Caldera. Castle of Oia and Panagia Platsani Church are also within 5 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 23 out of 24 reviews
Rating 8 - Good. 1 out of 24 reviews
Rating 6 - Okay. 0 out of 24 reviews
Rating 4 - Poor. 0 out of 24 reviews
Rating 2 - Terrible. 0 out of 24 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
From the communication before our trip through our stay our host was excellent! Danae, our guide, was super helpful with picking us up, taking us to the villa and showing us all the places to go and arranged our sailing trip! The place was perfect for our group and we got lots of excercise going up and down all the steps but that was expected considering the place is on the side of the cliff.The placed was cleaned every day and they supplied us with fresh fruits, bread, milk, ham and cheese, marmalade and wine!! Highly recommend this place!Thanks again for making our stay enjoyable and one we will never forget!!
Stayed 3 nights in Jul 2026
Response from VrboOwner on 23 July 2026
Thank you SO SO much dear Rene ! I hope you will be back "home some day !!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise in Santorini

We had a great stay! Katerina is wonderful and the villa is as beautiful and dramatic as in the photos (the view may even be more amazing in person if that’s possible)! The location in Oia is also perfect. We would definitely stay here again if we are fortunate enough to return to beautiful Santorini!
Stayed 4 nights in Jun 2019
Response from VrboOwner on 13 Sept 2023
Thank you so much ! It’s a big pleasure to have guests like you ! Come back “home” !!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful view and terrific location!

This place is about as conveniently located as you can get, and like many spots in Oia, the view is jaw-dropping. Working with Katerina makes the whole thing easy - she is super friendly and clearly dedicated to ensuring you have a great time!
Stayed 4 nights in Jul 2021
Response from VrboOwner on 13 Sept 2023
Thank you so much Kendal ! You were perfect guests and i wish you will be back "home" some day !!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property!

The property was amazing: location, layout, refreshing pool! Katerina was extremely responsive, helpful and we all had a wonderful time. Thank you!
Stayed 3 nights in Jul 2022
Response from VrboOwner on 13 Sept 2023
Τhank YOU, you were perfect ! Come back !
Verified review

10/10 Excellent

Best ever!

The villa is so beautiful and in such a great location. Katerina is very welcoming and will help you book any activities. Would definitely stay there again! Thanks Katerina!
Stayed 4 nights in May 2018
Response from VrboOwner on 13 Sept 2023
Ruth and Tim ! They are not only guests, they are my friends !! Excellent guests , perfect !! I hope they will come back again !!! Thank you !!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

September in Oia

Our Stay was wonderful. Katerina and Katia were so attentive and helpful in planning our activities. We highly recommend this rental and would not hesitate to return for another visit. Everything that was arranged for us was timely with very clear instructions.
Stayed 5 nights in Sep 2022
Response from VrboOwner on 13 Sept 2023
Thank you SO much ! You were so perfect guests and people ! Please come back "home" !!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house and view!

This house in Oía was absolutely prefect for the four of us (2 couples). The view was insane, and the location was great. Katerina made the whole process easy from start to finish, and even arranged all of our transportation! After this visit, we will definitely be back to Santorini and we hope we can get this same spot!
Stayed 3 nights in May 2022
Response from VrboOwner on 13 Sept 2023
`thank you SO much !! Come back !!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wow! Once in a lifetime villa

We had an amazing stay. This villa was breathtaking. The view was incredible. Sitting in the pool overlooking Santorini was amazing. Staying in a cave house was unique. Every detail was taken care including dinner reservations, luggage porters and laundry service. Katarina and her team was so lovely. I highly recommend!!!!!
Stayed 3 nights in May 2022
Response from VrboOwner on 13 Sept 2023
Thank you SO much lovely family ! You were perfect guests !! Come back !!!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

BEST HOST EVER!!

We can not say enough about Katarina. We have traveled the world many times and have never had such a host go to the lengths she did to ensure an incredible experience. The house was exactly as described. What an amazing experience. She was in constant contact, making sure we saw all the right places and ate all the right food. What an incredible human. Highly recommend.
Stayed 5 nights in Sep 2023
Response from VrboOwner on 20 Sept 2023
THE BEST GROUP EVER !!! It is so rare to have a group of people ALL fantastic, excellent persons, and PERFECT as guests !! Thank you SO much all of you ! Come back "home" !!!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dream Location, Amazing Host

Short Review since I left a longer one on another site, but briefly put....My family and I have wanted to visit Santorini for many years. As the COVID restriction finally loosened up in the EU, we took this opportunity and could not be more pleased. The location is everything that we imagined and is even better in person than on Google Images. Oia is the best place to stay on the Island and Katerina is a truly thoughtful and amazing host. She is both manager and owner and she not only provided a clean and comfortable villa with a "pinch me I must be dreaming" view, but helped us plan and reserve our activities during the week. This was well beyond the typical VRBO experience. Book this trip and you will not regret it. -Bobby and Jenn J.
Stayed 7 nights in Jun 2021
Response from VrboOwner on 13 Sept 2023
I can only say that you were the perfect people /guests !! Thank you !!!!! Come back !!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Views for days and days and days

After a slight hiccup to start (the luggage porter took us to the wrong villa so we had to spend one night in that one then change the next day!), the overall stay in Santorini was superb. Katerina’s place seems far away from the hustle and bustle because you can’t hear a single thing when you’re in the villa - bliss. However, the main walk way is literally a 3 minute walk up some steps to the top where you are near to a wealth of restaurants and rooftop bars. It’s so wonderfully well hidden but also close to everything you need. I think we took about 100 photos from the villa and we stayed here most of the time. The views are the best I have ever seen in my life. The villa has air con which is great and the house keeper who is very nice pops in every morning for a quick clean. The pool was a perfect temperature and much needed in the midday sun and Katerina had stocked the fridge with cheese, ham, cake and other bits, which was a nice touch. There was also plenty of bottled water too. Katerina was also near her phone for us to communicate with her which was very helpful. Santorini is just so breath-takingly beautiful - we can’t wait to go back. I will remember this weekend forever. Thank you, Katerina.
Stayed 3 nights in Jul 2021
Response from VrboOwner on 9 May 2025
Oh thank you SO much !! Come back !!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beyond Beautiful!

No pictures or videos can do justice to the unbelievable beauty of Oia and this villa is right in the middle of all it! Katerina went above and beyond as a host, and her villa felt like someplace out of a movie…it was perfect! We can’t wait to visit again!
Stayed 4 nights in Apr 2022
Response from VrboOwner on 13 Sept 2023
Thank you so much lovely girls !! I will wait for you cause you were perfect guests ! Thank you !!!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Santorini Oct. 2021

Perfect location, good housekeeping, free breakfast. I cannot imagine a better place. Thank you!
Stayed 5 nights in Oct 2021
Response from VrboOwner on 13 Oct 2023
Thank you !! Come back !!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Above All The Others

Owner/ operator Katerina was delightful and secured all transportation and reservations for us. Believe me- she knows all the local contacts! Amenities within the house included breakfast breads/ appetizers with welcome wine, soaps and shampoo. Expect MANY steps - which is the unique way that Oia stands out. The private pool was perfection and we were so thankful to have!
Stayed 3 nights in Aug 2021
Response from VrboOwner on 13 Sept 2023
Thank you SO much lovely girls !! I am sure you enjoy your stay ! Stairs yes, are for exercise sfter so good meals here, but the secret is.. slowly slowly !! You were all perfect !! THANK YOU !!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect stay!

We loved our stay at Katerina! It was centrally locates right off of the Main Street in Oia. Very close to shops and restaurants. Katerina was so wonderful. She planned an itinerary for us for our stay, was on call the entire time and was so sweet and knowledgeable. We left to visit another island and called begging to come back. She sets the bar high for other VRBO properties.
Stayed 3 nights in Oct 2019
Response from VrboOwner on 13 Sept 2023
I am so sorry i have no availability ... cause you are the perfect guests !! Thank you so much !!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Accommodations in Oia

We loved everything about this property! Katerina is a perfect host and arranged our transportation to and from the airport as well as gave recommendations on places to visit while in Santorini. The home is very traditional and in the PERFECT location. The pool is heated and we would definitely stay here again.
Stayed 2 nights in Oct 2019
Response from VrboOwner on 13 Sept 2023
Thank you my girls !! You were perfect guests !! I hope you will be back !!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Katerina is the best!

Katerina had coffee with us when we arrived and gave us an overview of the island. She was available by phone ALL THE TIME to help with everything. She met us when we left to say good-bye, too. The cave was well stocked with a bottle of sparkling wine, white wine, some breakfast treats, cheese and meats, coffee and milk, wonderful jams..... incredible. The house keeper, Anna, did a great job every day, too. The place is lovely, but it is 100 steps (we counted them) down from the main street. They helped with the bags, but if you don't have good mobility, it is not the place for you. The second bathroom is huge and beautiful, but it is down a set of spiral stairs. Four robes kept us comfy and the dipping pool is refreshing. The larger bedroom could easily sleep 2 additional people (for a total of 4 in that room). I was a bit nervous about making our outbound ferry on time based on Katerina's time estimate to get to the port - it did take twice as long as she said, but we really didn't need to be at the port an hour early - and there is nothing to do while hanging at the port. The port looks like complete chaos to the uninitiated.
Stayed 4 nights in Sep 2019
Response from VrboOwner on 13 Sept 2023
Thank you SO much !! You were wonderful !! Come back "Home" !!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Villa in the heart of Oia, Santorini

This place was fantastic. Spacious outdoor area with dining table, lounge chairs and pool overlooking the sea. But more importantly than the location and the villa itself were the amazing Katerina and Anna (property manager and housekeeper) that were so kind and helpful and made our stay absolutely perfect.
Stayed 7 nights in Sep 2019
Response from VrboOwner on 13 Sept 2023
Thank you SO much Karam and lovely family !! It was a big pleasure to have you here ! I hope some day you will be back "home" !!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our stay at Hercules villa

A wonderful week in Oia. We loved Hercules Villa, and Katerina was an exceptional hostess. Looking forward to returning. Thank you Katerina
Stayed 7 nights in Aug 2019
Response from VrboOwner on 13 Sept 2023
Perfect, perfect guests !!!! I love them all !!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property in a perfect location

My friend and I stayed here with our two teenage daughters. The property had a perfect location in Oia, close to shops and restaurants. It had everything we needed and more than we expected, including free laundry service, pool, breakfast food, and daily cleaning service. Katarina was helpful and informative, loved her insight into the area and recommendations. She helped us make some reservations and had great ideas to maximize our enjoyment of our stay. We would love to visit again and definitely would stay here next time. We couldn’t have been happier!
Stayed 5 nights in Jun 2019
Response from VrboOwner on 13 Sept 2023
Thank you girls !! I am happy only when i have happy guests like you ! You were perfect guests and it will be a big pleasure to have you here again ! You were perfect !!
Verified review

10/10 Excellent

Unbelievable location, accommodations and hospitality

Beautiful accommodations, views, location and surrounding areas
Stayed 3 nights in May 2019
Response from VrboOwner on 13 Sept 2023
A lovely lovely family! They real enjoyed their stay with respect. I wish I had guests like them ! And I wish they will come back « home » !!!
Verified review

10/10 Excellent

Ifestio Villa Hercules - Amazing!

We had such a wonderful time at Villa Hercules! Katerina is fantastic and gave us great recommendations for our stay. The place was beautiful and everything was absolutely perfect. We highly recommend staying at this place!
Stayed 4 nights in Apr 2019
Response from VrboOwner on 13 Sept 2023
Thank you SO much lovely yang family !! Come back !! You were perfect guests !!! All my best wishes !!
Verified review

10/10 Excellent

Stunning view

We had a lovely stay. Katherina helped us plan our three day stay including dinner reservations, car rental and airport transfers. The view from the large desk is awesome. The pool was a great place to enjoy an evening bottle of wine. Thanks
Stayed 3 nights in Sep 2018
Response from VrboOwner on 13 Sept 2023
Thank you SO mutch Kim and friends !! Perfect guests !!!
Verified review

10/10 Excellent

Amazing place to stay. Katerina was the perfect host, and made us feel so welcome.

Very spacious, with lots of private outdoor space and great views. The pool really is the icing on the cake. This place will provide an amazing Santorini experience.
Stayed 4 nights in Apr 2018
Response from VrboOwner on 13 Sept 2023
Oh, Thank you SO much !! I hope will be back "home "!!

About the host

Hosted by ifestio villas

Host profile image
I am an architect and I use to do my best for my guests !!

Why they chose this property

Because here you can live your dream !

What makes this property unique

FREE LAUNDRY !!
Champagne and best local volcanic wine for your welcome.
Free complete breakfast.
Fast free WI-FI
Olive oil, vinegard, salt, pepper, origan
greek sweets
Suggestions for best places to visit, best things to do, restaurants, attractions.

Languages:

English, French, Italian, Greek
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