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Cycladic house vacation rentals in Santorini caldera

Find and book unique cycladic house rentals on Airbnb

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Popular amenities for Santorini caldera cycladic house rentals

Family-friendly cycladic house rentals

Guest favorite
A person is seen relaxing by a small plunge pool with a tray of fresh watermelon slices nearby. Sun loungers and a large umbrella provide shade against the blue sky, while the landscape features distant hills and the ocean in the background.
Cycladic home in Oia
4.79 out of 5 average rating, 393 reviews

Cave house Oia Caldera Amazing view with Jacuzzi

MarcieRating, 5 stars7 months ago
The home was in the most ideal location with the most beautiful views! Jackie was so helpful with booking our transfers. The jacuzzi could have been hotter but we still enjoyed it! Would definitely recommend this place for the most authentic Santorini experience!!
Superhost
The interior features a spacious and airy living area with a curved ceiling. Two comfortable seating areas are arranged beside a kitchen equipped with modern appliances. A dining table is set with tableware, and soft lighting enhances the welcoming atmosphere.
Dome in Mesaria
4.97 out of 5 average rating, 145 reviews

Marla Villas - Cave House

JuliaRating, 5 stars3 days ago
Very happy with our stay!
Top guest favorite
A private terrace features a shimmering pool with views of the sea and the caldera. Whitewashed buildings in Oia line the cliffside under a clear blue sky, creating a serene backdrop for relaxation.
Villa in Oia
4.87 out of 5 average rating, 208 reviews

Top Caldera view villa with Hot Tub in Oia

KathrynRating, 5 stars3 weeks ago
Couldn’t recommend this more! Beautiful home with an amazing view and great hosts!
Top guest favorite
A wooden sign displaying the name 'Olyra Traditional Cave Houses' is mounted on a whitewashed wall, complemented by a rustic gate. Vibrant pink flowers enhance the entrance, adding a touch of natural color to the setting.
Cycladic home in Pyrgos Kallistis
4.96 out of 5 average rating, 132 reviews

Olyra Traditional Cave Houses 2

TressaRating, 5 stars2 weeks ago
The place was great! It was in a perfect location less than a 5 minute walk from a bus stop. Dimitra was extremely kind and helped us answer any questions we had. The place was exactly as pictured!
Top guest favorite
A serene outdoor space is highlighted, featuring sun loungers positioned by a swimming pool. The horizon glows with hues of orange and yellow as the sun sets, while a hanging chair gently sways nearby. Natural stone elements frame the view, adding texture to the scene.
Apartment in Fira
4.98 out of 5 average rating, 196 reviews

Saints Apostles Villa with private pool

LauraRating, 5 stars2 weeks ago
Wow! George was the best. We arrived late due to a flight delay and he stayed around to wait for us so he could show us all the local recommendations. We were blown away by how much food was in the fridge for us. Every time we asked for a ride into town, George himself was there within minutes. We woke up to two amazing sunrises, which you wouldn’t get anywhere else in the island. The villa was within walking distance to Fira. We would highly recommend this air bnb, it was perfect for two couples! A 10/10 experience!
Superhost
A clean outdoor patio area features a small table set with a tablecloth, surrounded by two wooden chairs with pink cushions. Whitewashed walls and windows with shutter-style openings create a bright and inviting space under a clear blue sky.
Apartment in Fira
4.83 out of 5 average rating, 120 reviews

Souita Mantilaria

OliviaRating, 5 stars3 days ago
Lovely stay. The host was wonderful and welcoming creating an amazing atmosphere. She also helped us arrange transfer from the port which was very helpful. Such a cozy place to stay in such a great area in Fira.
Guest favorite
A spacious terrace offers stunning views of the ocean and surrounding landscape. Three soft seating cushions are arranged on a smooth, light-colored surface, providing a comfortable space to relax. The horizon blends the sky and water, creating a serene backdrop.
Cycladic home in Oia
4.9 out of 5 average rating, 174 reviews

Ammos Oia Mansion

OliviaRating, 5 stars1 month ago
This is far and away the best experience I have ever had using Airbnb. The place was amazing--even better than we expected--and Elizabeth thought of everything. She met us for check in to walk us through everything, made recommendations and reservations, and was very timely in responding to questions. I cannot recommend this listing highly enough. 1000/10!
Top guest favorite
A modern living area features a curved, turquoise sofa against a white wall, complemented by decorative wall hangings. A dining table is positioned nearby, adorned with fresh flowers and food items. Natural light illuminates the space, enhancing its welcoming atmosphere.
Cycladic home in Megalochori
4.96 out of 5 average rating, 255 reviews

Villa Ruby

WendyRating, 5 stars2 weeks ago
Wonderful place! Georgia was soooo friendly and helpful with everything. The Airbnb is in the best location with deck views over the town and of the next door churches. We also fell in love with Megalochori, the cafe/tavern with exquisite live Greek music (across the "street"), the great village restaurants, the local artisans...all just steps away. Thank you, Georgia! Your amazing Cycladic home was perfect!

Cycladic house rentals with a patio

Top guest favorite
A private terrace is presented with a cozy seating area, featuring plush cushions in neutral tones. A small table holds a bottle of wine and two glasses, alongside a pineapple. The backdrop showcases a tranquil sea view during sunset, with soft hues in the sky.
Home in Oia
4.97 out of 5 average rating, 35 reviews

Lunar Sea Suite with Hot-tub and caldera view

AnthonyRating, 5 stars2 weeks ago
TL;DR Stunning air bnb. Very worth it for a first visit to Santorini. Booked Catherine’s room for our first visit to Santorini and it was fantastic. The views from the air BnB are even more beautiful than the pictures and the bed was very comfortable. It also came with an actual duvet which isn’t very typical from what we’ve experienced on other islands. She also provided a lot of services and assistance during the trip such as restaurant reservations, taxis, porters to move our suitcases to/from the post office and daily cleaning of the room. Note: the route to the air BnB is a bit precarious so it might not be suitable for people who are less active. The jacuzzi also isn’t as hot as jacuzzis in the states but was still very enjoyable. Also Santorini is experiencing a water shortage so there might be bouts where the shower/tap won’t be working but it doesn’t last very long.
A private hot tub with bubbling water is positioned on a terrace, surrounded by white walls. In the background, a traditional bell tower rises against the clear blue sky, adding a touch of local architecture. Sun loungers are placed nearby for relaxation.
Cycladic home in Akrotiri
5 out of 5 average rating, 13 reviews

Spilia Cave Nicole Santorini

SarahRating, 5 stars8 months ago
The cave house was exactly what me and my partner wanted for our trip. It is in a quiet part of Santorini and we felt like we had a lot of privacy. The cave looked just like the photos and was spotlessly clean. Bed and couch were comfortable. We also loved the jacuzzi on the roof. Nikoleta was very easy to communicate with and we had a great stay in her cave. Would definitely recommend it.
Superhost
A modern villa is set against a clear blue sky, featuring a spacious pool surrounded by wooden lounge chairs. The property includes multiple structures with white exteriors, accentuated by lush landscaping and steps leading to a peaceful outdoor area.
Cycladic home in Megalochori

Apelia Santorini Holiday Villa (Car Included)

OmarRating, 5 stars10 months ago
We had an amazing stay at the Airbnb! Upon our arrival, a car was waiting to take us to the house. When we walked in, we were pleasantly surprised to find food in the refrigerator, as the host had thoughtfully stocked it for us. The house was not only new but also impeccably clean and tidy, creating a welcoming atmosphere. The host was incredibly friendly and made us feel right at home, even giving us a tour of the property. The pool was maintained daily, ensuring a refreshing experience. Additionally, he provided us with a map and suggested various places to explore, making our stay even more enjoyable. Overall, we had a fantastic time and highly recommend this place!
Top guest favorite
A private jacuzzi is featured on the terrace, partially shaded by a dark curtain. The soothing water is illuminated in blue, with a backdrop of traditional Santorini buildings and a soft evening sky creating a calm atmosphere for relaxation.
Cycladic home in Megalochori
4.97 out of 5 average rating, 39 reviews

Argy's Luxury White Villa With Private Jacuzzi

AngelRating, 5 stars7 months ago
The stay at Argy’s was wonderful! We loved the location! It was a magical place in what felt like a small traditional village with the most delicious restaurant right at the bottom of the stairs! The hot tub was lovely (turn up the temp as soon as you arrive because it takes about 16 hours to heat up) and the deck was perfect for yoga and meditation. There was a generous bottle of wine.
Top guest favorite
A spacious outdoor dining area is set against a clear blue sea, featuring a wooden table surrounded by white woven chairs. Sunlight creates a bright atmosphere, with a shade sail overhead providing comfort. Scenic views of the coastline and mountains are visible in the background.
Cycladic home in Ormos Korfou
4.86 out of 5 average rating, 7 reviews

Petinos Traditional House

KateRating, 5 stars9 months ago
Stunning flat and stunning cove to stay in . Utterly peaceful and it felt like a true haven. Apostolo was a fantastic host and really was amazing in getting us to Santorini for our flights home when the local boat wasnt running . The fava in the windmill restaurant was the best we have ever tasted A million thank yous Apostolo .
An outdoor patio area is visible, featuring wooden dining furniture under a shaded structure. Soft lighting enhances the space as it transitions into evening. Steps lead down to an entrance framed by stone walls, surrounded by greenery and palm trees in the background.
Home in Mesaria
5 out of 5 average rating, 3 reviews

Euphemus Cave House

NikiRating, 5 stars9 months ago
The accomodation is lovely, spacious, clean, comfortable and modern. The area is quiet with narrow laneways meaning no cars just scooters and foot traffic - which was minimal and means you are not on a tourist route and it is lovely and peaceful. Evi kindly arranged transfer services from the airport to the accommodation for us, and also for when we wanted to go out to dinner one evening. These were much appreciated, Evi could not do enough for us.
Top guest favorite
A private terrace features a hot tub surrounded by sun loungers, with a view of the distant sea and rocky landscape. A palm tree adds a tropical touch, while a comfortable seating area is situated nearby, offering a serene outdoor space for relaxation.
Cycladic home in Vourvoulos
5 out of 5 average rating, 43 reviews

Beyond Crowds Seafront Escape | Sonus Mare 2

KerrinRating, 5 stars7 months ago
This home and host were nothing short of spectacular. It was the perfect space and view of both sunrise and moon rise! Iconic views from the very well maintained hot tub! I hope to be back!
Superhost
Two wooden lounge chairs with navy cushions are positioned beside a clear, inviting hot tub. The surrounding area features a smooth concrete surface, bathed in natural sunlight, accentuating a serene outdoor setting.
Apartment in Fira
4.91 out of 5 average rating, 56 reviews

Casa Bu 4 - 1Bedroom Apartment with Prive Hot-Tub

ElisabethRating, 5 stars2 weeks ago
We really enjoyed our stay at Case Bu! The hosts are friendly, quickly responsive, and very accommodating. The location is perfect- a quick, easy walk to many, many wonderful restaurants, all with excellent food and drink/coffee, and the bus station is only a 10 minute walk. The buses are very nice and comfortable- we took day trips to Oia, Perissa black beach and Akrotiri red beach. The room was lovely- small but cozy, clean and comfortable with everything you might need, and we loved having a private enclosed sitting area with a small pool/tub. The surrounding area is safe, quiet and so beautiful!! Thank you for sharing your wonderful space with us!!

Cycladic house rentals with a washer and dryer

Superhost
A hot tub is seen on a balcony, offering a view of the calm Aegean Sea and surrounding landscapes. The railing features a decorative design, and the sky above is partly cloudy, adding to the serene atmosphere.
Apartment in Ia
4.65 out of 5 average rating, 100 reviews

Captain’s studio twin beds with sea view in Oia

MohamedRating, 5 stars1 week ago
One of the best places in Oia , john is friendly , the view is amazing , i ll come back for sure on my next vacations in Oia 👋🏻
Guest favorite
A serene outdoor space is showcased, featuring a circular seating arrangement overlooking the vast blue Aegean Sea. The landscape includes whitewashed structures and steps leading to the balcony, framed by clear skies and distant cliffs along the coastline.
Windmill in Oia
4.94 out of 5 average rating, 65 reviews

The Sunset Windmill

KyraRating, 5 stars1 month ago
We had a wonderful stay . The house,location and views were amazing . Jason 100% made the stay even better with his wonderful spread of breakfast every morning . He was so helpful with recommendations , helping us rent a car and so accommodating. The only downfall ( which we knew in previous reviews ) was the traffic of people and vacant lot . Not a lot of privacy. But to be honest , we were not at the house all that much . After sunset it's pretty private and peacefully quiet. I wouldn't choose another place knowing we were so well taken care of and the benefits you get in staying there .
Superhost
A clear blue pool reflects the white architecture of the villa and the surrounding mountain landscape. Sun loungers are arranged on the deck beside the pool, and a large umbrella provides shade. Lush greenery outlines the pool area, enhancing the serene setting.
Dome in Kamari
4.91 out of 5 average rating, 11 reviews

Felicity Villas Santorini - Victoria

RobertRating, 5 stars11 months ago
This house is an excellent option for a trip to Santorini. It is in an excellent location, has wonderful hosts, close to the airport, beautiful surroundings and pool. The house has a maid who comes to clean every day. Margarita made us a cake and brought it to us on the first day of our stay. The house is a 5 minute walk to a grocery store, 10 minute walk to the bus stop to go to Fira, and 10-15 minutes walk to Kamari beach. I’d definitely stay here again. Thanks to Margarita and her family for hosting us.
Guest favorite
A private balcony features sunbeds and a lounge chair, inviting relaxation with expansive views of the caldera. The bright blue sky and serene sea provide a picturesque backdrop. Light-colored furnishings enhance the open atmosphere, complemented by the tranquil setting.
Apartment in Pyrgos Kallistis
4.79 out of 5 average rating, 33 reviews

Genesis Suite | Sea view & outdoor hot tub

Bethany-RoseRating, 5 stars2 weeks ago
Love love loooove this accommodation! Georgia was an amazing host who went above and beyond to make sure our stay was one to remember. She was so proactive and helpful, made our journey to and from the port a breeze and went the extra mile 🥰 definitely one of our favourite listings, the staff are so sweet and friendly, the views are to die for and our place felt so luxurious! Thank you again to Symphony Suites and Georgia for making our stay a very pleasurable one, we’ve loved our stay in Santorini 🤍
Top guest favorite
A spacious terrace is set for outdoor dining, featuring a wooden table with plates arranged neatly. Soft lighting enhances the serene atmosphere, while a fading sunset casts warm hues across the sky. The door to an interior space is visible, adding context to the area.
Cycladic home in Pyrgos Kallistis
4.96 out of 5 average rating, 259 reviews

Santorini Mayia Cave House with Private Cave Pool

AnnaRating, 5 stars1 week ago
What a find. This area is less touristy but has all you need. Amazing restaurants, view points, car and buggy rentals. The house it self is as described. Perfect! We cooked dinner and ate on the terrace during sunsets, no bugs. Many friendly people around. All you need for coffee is provided. Cooking utensils and pans were good enough. Found I needed an extra bowl but as luck would have it there was a local market that was selling beautiful bowls. Also there is Maria market that had all the necessities. Be ware of things that don’t have a price. Over all we had an amazing stay and our host was very prompt, kind and responsive!
Guest favorite
The image captures a modern apartment entrance with a charming archway. A small seating area is visible beside a bright window. The background features traditional white buildings and a distant church tower, set against a blue sky with soft clouds.
Apartment in FIROSTEFA
4.94 out of 5 average rating, 71 reviews

Airth Suite (jacuzzi and sunset view)

DebraRating, 5 stars3 weeks ago
This was a perfect place to stay in the Firostefani village of Santorini! The location was very convenient - right on the 'walk' but quieter than staying directly in Fira. There were wonderful views directly from the front and there were many restaurants and shops very close by. It is also a very short walk to the hustle and bustle of Fira and we did it each day with no worries. Everything in the apartment was so clean and comfortable, including the outdoor hot tub which we enjoyed! The place is very spacious and had everything we needed, and our host welcomed us with warm Greek hospitality, providing an orientation to the area and recommendations for restaurants, and even assisted with booking a Catamaran tour - which I would recommend as well. Overall we felt so relaxed and comfortable during our time and highly recommend this place for the views, comfort, convenience, and exceptional service. A+
Superhost
A spacious bedroom is illuminated by natural light from the double doors opening to a terrace. The room features a large bed with white linens, accompanied by a cozy accent pillow. Soft curtains frame the doorway and a circular rug adds warmth to the polished floor.
Cycladic home in Santorini
4.82 out of 5 average rating, 104 reviews

Bluewhite villa with heated private pool

CallumRating, 5 stars2 weeks ago
Highly recommend staying here, one of the best views I’ve ever seen. Place was beautiful, situated right next to a local town which was amazing. Pool was absolutely stunning along with the house, if anything the pictures do not do enough justice for how nice this place is. Ina was our host who was so friendly and helpful, gave us recommendations, always responsive and even was able to sort us travel. Definitely will be coming back!
Guest favorite
Cycladic home in Finikia
4.89 out of 5 average rating, 236 reviews

Villa Florina

DanaRating, 5 stars1 week ago
Stefanos and Natasa were amazing hosts! Quick to respond, helpful, and friendly. Stefanos coordinated pick up/drop off from the airport and met us personally to walk my family to our Airbnb. If you decide to use the shuttle service, ask Stefanos to try and book Theo as your driver (if he's available!). He shared great information along the ride, and we asked Stefanos to book him as our guide for a personal tour of the island ~ this was one of our most favorite days! The traditional cave house was exactly as described, worked perfectly for our family of seven (4 adults, 3 teenagers), offered amazing family space in the courtyard and spectacular views and sunsets from the rooftop patio!!! My entire family would highly recommend this property and hopes to return to beautiful Santorini!

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