See all properties

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

Top rated by guests

Terrace/patio

Private kitchen

Outdoor dining

Property grounds

Exterior

9.9Outstanding

(23 Ratings)

Host Katerina's exceptional care and attention ensured an amazing experience from start to finish. Highly recommended for an unforgettable stay.

From real guest reviews summarized by AI

Don't miss out! Price and availability may change

9.9 / 10.0

Outstanding(23 Ratings)

Villa in Oia

6 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Top-tier experienceA high end property in this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this villa rental

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 !

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

Pets allowed

Map of Oia

city location on map

Nearby attractions

Akrotiri Lighthouse

Santorini Wine Museum

Museum of Prehistoric Thera

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Vrbo provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vrbo

$$$$

Top rated by guests

9.9Outstanding

(23 Ratings)

Host Katerina's exceptional care and attention ensured an amazing experience from start to finish. Highly recommended for an unforgettable stay.

From real guest reviews summarized by AI

Don't miss out! Price and availability may change

$$$$

9.9 / 10.0

Outstanding(23 Ratings)

Villa in Oia

6 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Top-tier experienceA high end property in this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Map of Oia

city location on map

Nearby attractions

Akrotiri Lighthouse

Santorini Wine Museum

Museum of Prehistoric Thera

About this villa rental

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 !

Amenities

Pets allowed

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Vrbo provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vrbo

Ratings and reviews

9.9 / 10.0

Outstanding(23 Ratings)

Summary of reviews

Host Katerina's exceptional care and attention ensured an amazing experience from start to finish. Highly recommended for an unforgettable stay.

From real guest reviews summarized by AI

10.0 / 10.0

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.

10.0 / 10.0

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.

10.0 / 10.0

Amazing property!

Amazing property!

The property was amazing: location, layout, refreshing pool! Katerina was extremely responsive, helpful and we all had a wonderful time. Thank you!

10.0 / 10.0

Wow! Once in a lifetime villa

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!!!!!

10.0 / 10.0

Beautiful house and view!

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!

10.0 / 10.0

Beyond Beautiful!

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!

8.0 / 10.0

Santorini Oct. 2021

Santorini Oct. 2021

Perfect location, good housekeeping, free breakfast. I cannot imagine a better place. Thank you!

10.0 / 10.0

Above All The Others

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!

10.0 / 10.0

Beautiful view and terrific location!

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!

10.0 / 10.0

Views for days and days and days

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.

10.0 / 10.0

Dream Location, Amazing Host

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.

10.0 / 10.0

Perfect stay!

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.

10.0 / 10.0

Perfect Accommodations in Oia

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.

10.0 / 10.0

Katerina is the best!

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.

10.0 / 10.0

Beautiful Villa in the heart of Oia, Santorini

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.

10.0 / 10.0

Our stay at Hercules villa

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

10.0 / 10.0

Paradise in Santorini

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!

10.0 / 10.0

Beautiful property in a perfect location

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!

10.0 / 10.0

Unbelievable location, accommodations and hospitality

Unbelievable location, accommodations and hospitality

Beautiful accommodations, views, location and surrounding areas

10.0 / 10.0

Ifestio Villa Hercules - Amazing!

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!

10.0 / 10.0

Stunning view

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

10.0 / 10.0

Best ever!

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!

10.0 / 10.0

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

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.

Explore similar stays in Oia

Explore all rentals in Oia

8.6 / 10.0

Excellent(16 Ratings)

Caldera View by Caldera Houses

6 guests · 3 bedrooms · 3 baths

Family friendly

Looking for the perfect place to call home during your trip to Oia? This Villa offers a comfort and style with top-notch amenities, including Family friendly, and more.

10.0 / 10.0

Outstanding(1 Rating)

ArmonOia Caves

2 guests · 1 bedroom · 1 bath

Air conditioner · Internet / Wifi · Balcony or Patio

Soak up the beauty of Oia in our Apartment, ArmonOia Caves. With a range of amenities such as Air conditioner, Internet / Wifi and Balcony or Patio, you'll feel right at home.

10.0 / 10.0

Outstanding(1 Rating)

ArmonOia Caves

2 guests · 1 bedroom · 1 bath

Air conditioner · Internet / Wifi · Balcony or Patio

This Apartment in Oia, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

8.7 / 10.0

Excellent(31 Ratings)

Chroma Suites

2 guests · 1 bedroom · 2 baths

Air conditioner · Internet / Wifi · Balcony or Patio

Apartment in Oia, for $429 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

9.6 / 10.0

Outstanding(105 Ratings)

Armeni Luxury Villas

2 guests · 2 bedrooms · 2 baths

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking to create some memories in Oia? Look no further than our Villa, Armeni Luxury Villas. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

Mesmerizing Santorini Villa | 3 Bedrooms | Beautiful Sea & Sunset Views

7 guests · 3 bedrooms · 1 bath

Family friendly

Looking for a Villa in Oia, this Villa for $355 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

9.6 / 10.0

Outstanding(105 Ratings)

Armeni Luxury Villas

2 guests · 2 bedrooms · 2 baths

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking for a Villa in Oia, this Villa for $343 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

Traditional Cycladic house with sea view

7 guests · 3 bedrooms · 2 baths

Pets allowed · Family friendly

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Oia, at $371 per night for your next great vacation.

10.0 / 10.0

Outstanding(4 Ratings)

Traditional Santorini Villa | Adrales Cave House | 3 Bedrooms | SeaViews

6 guests · 3 bedrooms · 1 bath

Family friendly

Experience vacation in Oia with our Villa, Traditional Santorini Villa | Adrales Cave House | 3 Bedrooms | SeaViews. Enjoy amenities such as Family friendly, and more.

9.8 / 10.0

Outstanding(53 Ratings)

Luxus VIP Suites

2 guests · 1 bedroom · 1 bath

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Soak up the beauty of Oia in our House, Luxus VIP Suites. With a range of amenities such as Air conditioner, Internet / Wifi and Kitchen or Kitchenette, you'll feel right at home.

9.8 / 10.0

Outstanding(53 Ratings)

Luxus VIP Suites

2 guests · 1 bedroom · 1 bath

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Oia, at $352 per night for your next great vacation.

9.0 / 10.0

Outstanding(2 Ratings)

Amazing Santorini Villa | Anima Residence | 3 Bedrooms | Astounding Views

6 guests · 3 bedrooms · 1 bath

Villa in Oia, for $348 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

9.2 / 10.0

Outstanding(6 Ratings)

White Cave Villa by Caldera Houses

4 guests · 1 bedroom · 1 bath

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Soak up the beauty of Oia in our Villa, White Cave Villa by Caldera Houses. With a range of amenities such as Air conditioner, Internet / Wifi and Balcony or Patio, you'll feel right at home.

Traditional Cycladic house with sea view

7 guests · 3 bedrooms · 2 baths

Pets allowed · Family friendly

Looking for the perfect place to call home during your trip to Oia? This House offers a comfort and style with top-notch amenities, including Pets allowed and Family friendly, and more.

9.0 / 10.0

Outstanding(6 Ratings)

White Cave Villa by Caldera Houses

4 guests · 1 bedroom · 1 bath

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This attractive Villa in Oia, $378 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

10.0 / 10.0

Outstanding(2 Ratings)

Amarie House with Sea View and Sunset View

6 guests · 3 bedrooms · 1 bath

Family friendly

The best choice in Oia for House, for $358 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

Wonderful Santorini Villa | 2 Bedroom Villa | Outdoor Pool & Stunning Views

6 guests · 2 bedrooms · 2 baths

Family friendly

Indulge in a peaceful retreat at Wonderful Santorini Villa | 2 Bedroom Villa | Outdoor Pool & Stunning Views, our elegant Villa in Oia. Enjoy amenities including Family friendly, and more.

9.8 / 10.0

Outstanding(153 Ratings)

Aris Caves

2 guests · 1 bedroom · 1 bath

Air conditioner · Internet / Wifi · Balcony or Patio

Enjoy the best of Oia in our Apartment, Aris Caves. A stunning property with amenities including Air conditioner, Family friendly and Internet / Wifi, and more.

7.6 / 10.0

Good(4 Ratings)

Rhenia Suites-Prive Jacuzzi&Caldera View

3 guests · 1 bedroom · 1 bath

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Business stays, family stays, couples stay, getaway vacation, and rental in Oia at Rhenia Suites-Prive Jacuzzi&Caldera View for $364 for your next trip.

7.6 / 10.0

Good(4 Ratings)

Rhenia Suites-Prive Jacuzzi&Caldera View

3 guests · 1 bedroom · 1 bath

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Villa in Oia, for $364 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

10.0 / 10.0

Outstanding(2 Ratings)

Amarie House with Sea View and Sunset View

6 guests · 3 bedrooms · 1 bath

Family friendly

Experience the best of Oia with this House available for $358. This property is equipped with amenities including Family friendly, and more.

Sculptors cave house, Santorini by Cycladica

6 guests · 2 bedrooms · 1 bath

Pets allowed · Family friendly

This inviting Villa in Oia can fit your needs for many types of vacations, at $439 per night.

Sculptors cave house, Santorini by Cycladica

6 guests · 2 bedrooms · 1 bath

Pets allowed · Family friendly

Experience vacation in Oia with our Villa, Sculptors cave house, Santorini by Cycladica. Enjoy amenities such as Pets allowed and Family friendly, and more.

9.4 / 10.0

Outstanding(7 Ratings)

Passion Blue Villas

3 guests · 1 bedroom · 1 bath

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

When traveling to Oia, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $337 per night.

9.4 / 10.0

Outstanding(7 Ratings)

Passion Blue Villas

3 guests · 1 bedroom · 1 bath

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

When traveling to Oia, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $337 per night.

You can save with One Key

9.4 / 10.0

Outstanding(3 Ratings)

White Cellar Cave houses Oia Santorini by Cycladica

6 guests · 2 bedrooms · 2 baths

Pets allowed · Family friendly

The best choice in Oia for House, for $398 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

Skala Cave by Thireon 3-bedroom villa in enchanting Oia with AC, Splash Tub

6 guests · 3 bedrooms · 2 baths

Pets allowed · Family friendly

Experience vacation in Oia with our Villa, Skala Cave by Thireon 3-bedroom villa in enchanting Oia with AC, Splash Tub . Enjoy amenities such as Pets allowed and Family friendly, and more.

2.0 / 10.0

(1 Rating)

Platis Residence Villa

6 guests · 2 bedrooms · 3 baths

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Indulge in a peaceful retreat at Platis Residence Villa, our elegant Villa in Oia. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more.

Skala Cave by Thireon 3-bedroom villa in enchanting Oia with AC, Splash Tub

6 guests · 3 bedrooms · 2 baths

Pets allowed · Family friendly

Are you ready to indulge in a relaxing getaway? Our Villa in Oia has everything you need for a rejuvenating stay. Treat yourself to Skala Cave by Thireon 3-bedroom villa in enchanting Oia with AC, Splash Tub 's exceptional amenities, such as Pets allowed and Family friendly.

2.0 / 10.0

(1 Rating)

Platis Residence Villa

6 guests · 2 bedrooms · 3 baths

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Experience the best of Oia with this Villa available for $441. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.