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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

ChristelleRating, 5 stars3 weeks ago
Séjour parfait! Il est très bien situé à Oia avec vue à couper le souffle et jacuzzi à bonne température pour le soir. Jackie est très attentionné et toujours prêt à aider. Je conseille de prendre le portier pour les bagages, car l’accès est un peu compliqué, mais ça vaut le coup. Il est spacieux, bien décoré, avec un matelas très confortable. Terrasse, table, parasol et jacuzzi sont privés. Il y a juste l’appartement au-dessus qui a un droit de passage sur la terrasse. Une séparation par un muret bas avec les voisins ne limite pas l’intimité, mais permet de profiter d’une magnifique vue. L’eglise voisine attire beaucoup de touristes, ce qui peut troubler un peu le calme en terrasse. Invasion de fourmis vite gérée. Coupures d’électricité possibles sur l’île. Accès moins pratique pour personnes à mobilité réduite, surtout pour la terrasse en hauteur. Jolie salle de bain, un pommeau fixé en hauteur serait un plus. Début de sunset splendide, mais on ne voit pas la fin 😊 Je recommand
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, 144 reviews

Marla Villas - Cave House

AzucenaRating, 5 stars2 weeks ago
Host was very helpful in answering questions and offering suggestions.
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, 131 reviews

Olyra Traditional Cave Houses 2

JessicaRating, 5 stars4 weeks ago
It was super helpful that Dimitra met us near the bus stop which dropped us off from the ferry destination. Bus schedule to Fira/Oia were a little confusing but we were able to figure it out soon after we got settled and it was a very nice adventure all around. The local people were very nice everywhere we went in Pyrgos. It was beautiful to hear the church bells early in the morning. The Airbnb was much bigger than expected. Super cool being in the caves. Just like the photos. The surroundings were stunning and amazing views. A little rough going uphill with luggage but not super unbearable and we made it work. Dimitra helped and we were very happy to have picked that location. Although the bus ride was about 30 minutes (to Fira), the scenery was beautiful.
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 stars1 week 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!
Guest favorite
A private outdoor area features a jacuzzi tub surrounded by a sun terrace. A dining table with seating for four is positioned near a cozy lounge area with cushions. Neutral-toned walls complement the space, creating a bright and open atmosphere.
Cycladic home in Karterádos
4.84 out of 5 average rating, 275 reviews

il Melograno Traditional Cave House

KellyRating, 5 stars2 weeks ago
Rodoula’s place was fantastic!! Its minimalistic beauty was exactly as pictured. We were only on the island for 1 day and 1 night but would have loved to spend more time in this gorgeous place.
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!
Guest favorite
A charming interior features a spacious bed draped with soft curtains, complemented by a daybed adorned with decorative pillows. A small table sits on a round woven rug, adding a cozy touch to the tile floor, while a wall clock and framed artwork enhance the tranquil ambiance.
Cycladic home in Finikia
4.78 out of 5 average rating, 209 reviews

Cosy Cave House

SierraRating, 5 stars8 months ago
Had a wonderful stay at Alexandra’s cave house! In a beautiful area with the best restaurant we went to in Santorini nearby (Lefkes). We loved how peaceful the area was, while being close enough to walk to Oia. She was very responsive, friendly, and helpful. Definitely recommend this Airbnb!
Top guest favorite
A serene outdoor area is highlighted by a clear blue pool, surrounded by comfortable sunbeds and a large umbrella. Lush greenery, including cacti, adds a natural touch to the space, creating a relaxing setting for guests.
Guesthouse in Mesaria
4.91 out of 5 average rating, 320 reviews

Studio with pool view

MariemRating, 5 stars1 week ago
We’re so grateful to Ida for making our stay truly unforgettable ! The accommodation is absolutely charming, authentically Greek .. with a lovely swimming pool and a terrace perfect for soaking up the Mediterranean sun ☀️ Mesaria is a great location, close to many key spots on the island, and Ida was incredibly helpful in recommending the must-see places. We couldn’t recommend staying at Ida’s place more 🤩

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, 34 reviews

Lunar Sea Suite with Hot-tub and caldera view

SarahRating, 5 stars5 days ago
There are not enough stars to describe how amazing Catherine was! The place and the views, were out of this world! From the moment we arrived they helped bring our luggage to the Airbnb and she greeted us with such kindness. She set up any and all reservations we requested, including meals and any day trips or activities. She was truly the best host I have ever had, would recommend her to anyone, we will be back!!
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.
Cycladic home in Fira
4.74 out of 5 average rating, 62 reviews

Aeron Suite Villa w. Queen Bed Sea & Mountain View

BenjaminRating, 5 stars1 month ago
Très bon Airbnb je recommande.
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.
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

PatrickRating, 5 stars9 months ago
Diese Wohnung ist ideal um die ganze Insel zu entdecken. Sie liegt am Ende einer kleinen Stichstraße die in einen Fußweg übergeht, der nach Messaria hineinführt. Wir gehörten zu den ersten Mietern, alles war neu, supersauber und gut eingerichtet. Hier fehlte es an nichts. Vor allem die Küche war sehr gut ausgestattet. Wasch- und Spülmaschine waren eine große Hilfe. Die Klimaanlagen haben perfekt funktinioniert, ebenso das wlan, das allerdings kaum auf die Dachterrasse reicht. Wir haben die Terrasse jeden Morgen und Abend gerne genutzt und dabei in der Ferne das Meer gesehen. Wir wurden sehr freundlich empfangen und gleich mit Wasser/Kaffee/Tee versorgt und zum Schluss gab es sogar eine kleine liebe Aufmerksamkeit.
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

ElinaRating, 5 stars4 weeks ago
Incroyable ! Les mots me manquent pour décrire ce Airbnb qui est sans aucun doute le meilleur dans lequel nous ayons pu séjourner. Points forts : - localisation à 10mn de Fira en voiture, a mi chemin de tous les points d’intérêts - un havre de paix en face de la mer, même si il y a plusieurs logements on ne ressent pas du tout le vis à vis - le jacuzzi incroyable en face de la mer a bonne température - la beauté de l’appartement - tous les petits cadeaux vraiment adorables avec un petit déjeuner + le ménage fait au milieu de notre séjour ce qui est très rare dans un airbnb Leur gentillesse est également un gros avantage Petit conseil pour les voyageurs, prenez une voiture, peu d’endroits sont accessibles à pieds d’autant plus que la villa se trouve en hauteur d’une montée :)
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 stars1 week 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

Guest favorite
The image captures a private swimming pool reflecting clear blue skies. Two striped deck chairs are positioned on the poolside, inviting relaxation. The villa's white exterior and large windows provide a serene backdrop against the tranquil water.
Home in Exo Gialos Karteradou
4.96 out of 5 average rating, 25 reviews

"Sand" sea view luxury villa with pool by beach !

DeborahRating, 5 stars1 month ago
The house is beautiful, just down from a very quiet beach. It was clean and exactly as described in the listing with plenty of space for our family. To note, it is near the airport with flights audibly departing throughout the day but these were very fleeting and did not disrupt our day. Maria helped us arrange a car which made it convenient to get around. It was a really nice, tranquil place to hang out at the pool at night.
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 stars6 days 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, 64 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
An outdoor space features a modern pool with crystal-clear water reflecting sunlight. A round lounge chair is positioned beside the pool, where a person can be seen relaxing. Glasses are placed on a nearby surface, suggesting a welcoming atmosphere.
Cycladic home in Megalochori
4.97 out of 5 average rating, 29 reviews

Samsara - Santorini Luxury Retreat

Paris Rating, 5 stars8 months ago
We had a wonderful stay at Samsara. It is a beautiful and peaceful villa with everything you need to have a relaxing time. The villa is in fantastic condition and well maintained. Andreas is a great host, always available to answer questions, arrange transportation or anything you need. We really appreciated the flexible check in and out times as we came and departed by ferry which only had one per day. We would not hesitate to book here again.
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 a Jacuzzi, with the sea view visible through large open windows. A comfortable sitting area is provided, set against the backdrop of Santorini's landscape. A bowl of fresh fruit sits nearby, enhancing the serene atmosphere.
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 🤍
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 stars2 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
An aerial view captures a private infinity pool, featuring clear turquoise water surrounded by a light-colored patio. Sun loungers and round stools are positioned nearby. A person relaxes by the pool, adorned in a pink swimsuit and a wide-brimmed hat, creating a peaceful scene.
Cycladic home in Santorini
4.83 out of 5 average rating, 103 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!

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