
Vacation rentals with a pool in Santorini caldera
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Top-rated rentals with a pool in Santorini caldera
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Santorini caldera rentals with a pool
House rentals with a pool
Top guest favourite

Home in Oia
4.92 out of 5 average rating, 60 reviewsChrista's home
NinaRating, 5 stars7 months ago
We had the most incredible stay at Christa’s home. We couldn’t believe how lucky we were to find this gem! Christa was a wonderful host, the location is just 2 minutes from the centre of everything yet it’s so peaceful, there is a shop and taxi rank at the end of the drive, the apartment was clean and perfect. The animals we felt really made the experience, they would greet us every morning and we loved getting to know their individual personalities. We found it difficult saying goodbye to them all! Christa very kindly arranged the airport transfers for us, sent us recommendations and informed us of a firework event that was happening in Fira. We also watched some beautiful sunrises and sunsets from the garden. Personally we think this is a better option than staying in the centre as some of the hotels are rather overlooked, whereas this offers a peaceful, secluded retreat but at the same time you get to experience beautiful Oia! We 100% recommend staying, it’s a very special place!
Superhost

Home in Θήρα
4.9 out of 5 average rating, 154 reviewsSTILVI SUITE
KaryRating, 5 stars7 months ago
Don’t think twice! If it’s available you’re lucky and should book it! The views are breathtaking and the inside is so unique and picture perfect. Yes, during the day there is foot traffic, but you will hear nothing but compliments and it will make you feel like a celebrity. Having the pool is so very nice and relaxing. In the evening the foot traffic is less for more privacy in the pool. You just can’t beat the views and a super host that helped us with transfers and local recommendations. Galini and Volkan are must try restaurants in walking distance. We really enjoyed the breakfast and both! Georgia is an artist and the decorations and painting in the house reflect her talents. We loved everything about this place and would love to return one day.
Guest favourite

Home in Karterádos
4.91 out of 5 average rating, 64 reviewsTriple garden view(3)
ElisaRating, 5 stars7 months ago
io e mia sorella abbiamo alloggiato in questa camera per 4 notti e non potevamo fare scelta migliore! zona molto tranquilla, vicina all'aeroporto e se si ha la macchina è vicina a tutte le principali attività turistiche. camera molto accogliente e zona comune con piscina curata nei minimi dettagli, host sempre disponibili e amichevoli pronti ad aiutare per rendere la vacanza leggera e rilassante. grazie per questi giorni fantastici 🧿🩵🙏
Top guest favourite

Home in Pyrgos Kallistis
4.97 out of 5 average rating, 123 reviewsAROMA CAVAS Suite with caldera view
LauraRating, 5 stars4 days ago
Nikos is a great host, very helpful and welcoming! The authentic greek hospitality! The place is clean, confortable with a great view and all the amenities needed. The place is less than 5 minutes away from good restaurants and supermarkets. I recommend Nikos's apartment! Thanks again for everything!!
Superhost

Home in Panagia Kalou
4.76 out of 5 average rating, 21 reviewsSantorini's Rising Sun Private Villa
Luca Rating, 5 stars8 months ago
Il nostro soggiorno in Villa è stato meraviglioso. La villa è molto bella e l'host è stato molto gentile e disponibile nelle comunicazioni. Consigliamo questa villa e speriamo di tornarci al più presto.
Top guest favourite

Home in Santorini
4.94 out of 5 average rating, 17 reviewsLe Grand Blue Villa with Private Pool & Sea View
RogerRating, 5 stars6 months ago
What a great place to stay in Santorini. We loved our six days. Tony greeted us and gave us lots of information and advice. The outside space is massive with plenty of places to relax and watch the boats go by. Many good restaurants within a few minutes walking distance. We walked around locally for the first part of our stay and only hired a car for just a couple of days at the end to explore a little further afield. Two mini markets (5 mins and 15 mins walking) had all we needed for breakfasts and snacks plus wine, beer and water. The accommodation is perfect for four people and there is lots of shaded seating around the building if you don’t want to get a tan. Note the pool is a small plunge pool. Great for cooling off, but don’t expect to do a workout in it. You can always swim in the sea for that. Add this to your list if you are looking for a relaxing location with great views.
Guest favourite

Home in Mesaria
4.95 out of 5 average rating, 164 reviewsVilla Helena Santorini- Private Plunge Pool & BBQ
OlivierRating, 5 stars1 week ago
Nous avons passé un très bon séjour à Santorin dans le logement d'Elena, qui est spacieux, fonctionnel et très propre. Elena est une hôte très réactive, à l'écoute et qui propose des informations et conseils sur les activités et les sites à voir, ce qui permet de passer un excellent séjour. Nous recommanderons le logement d'Elana à nos proches qui souhaiteraient se rendre à Santorin.
Superhost

Home in Fira
5 out of 5 average rating, 5 reviewsInspire Santorini Luxury Villas - B2
ThomasRating, 5 stars11 months ago
Mon séjour chez Ruben a été tout simplement exceptionnel grâce à l'accueil et au service irréprochable.Dès mon arrivée, j'ai été accueilli avec chaleur et professionnalisme. Ruben s'est montré incroyablement attentif à tous les détails, assurant que chaque aspect de mon séjour se déroule parfaiteme Il est rare de trouver un hôte aussi dévoué et passionné par l'accueil de ses invités. Grâce à Ruben j'ai pu me sentir comme chez moi tout en bénéficiant d'un service digne des plus
Condo rentals with a pool

Condo in Perissa
4.71 out of 5 average rating, 17 reviewsMaisonette 30 meters from Perissa Beach
Aman DineRating, 5 stars8 months ago
Noud venons de passer 9 jours de vacances superbe. Le logement est propre et bien entretenu par la femme de service que nous remercions. La climatisation est fonctionnelle. La piscine est vraiment top! ensoleillée l'après midi et ombragée vers le milieu de l'après midi ce qui est vraiment un Atout. Tout est accessible à pieds, et nous avions même le parking privé. Le logement est situé en plein centre de Perissa face à la mer. c'est juste génial avec des enfants. Le personnel est très agréable, les réceptionnistes toujours souriantes, agréable, et disponible pour nous aider dans nos recherches. je recommande vraiment cet endroit. encore merci
Guest favourite

Condo in Imerovigli
4.95 out of 5 average rating, 77 reviewsFamily Maisonette Sea-Sunset Suite Outdoor Jacuzzi
ShelbyRating, 5 stars10 months ago
If you asked me what the worst part of staying here was, it would be that the shower is so big I had to walk across to grab my shampoo! So not a bad thing at all! I was in communication prior to our stay as it was going to be my mom’s birthday while we were there. Our host arranged a beautiful wine tour of the island and a private dinner at sunset, and a specialized cake, it was the best birthday I could provide for my mom! Speaking of sunset, forget staying in Oia, while I am sure it is beautiful, nothing can compare to the beauty and ease of the sunset at this location. One evening there were two other people that were close for sunset, and that was it. They also provide easy transports between Oia and Fira so you don’t have to worry about trying to walk when it gets too hot out. Oh, and let me tell you. The breakfast that is provided here is seriously the best! So many different breakfast options right to your room. This was definitely the best breakfasts we had while in Greece!

Condo in Fira
4.67 out of 5 average rating, 3 reviewsAkrotiri Santorini Two bedroom apartment & pool
GaryRating, 5 stars22 months ago
Mr. Kostas reached out to us in plenty of time, set everything up from our transfers, rental cars, excursions, dinners, sunset cruise, etc. He MADE out trip and helped us experience everything we wanted to do in Santorini and maximized all of our available time. He is simply the best! We are forever grateful! for him! The villas we quiet and relaxing, food, drinks, service was top notch. All the staff were extremely helpful and kind. Vitali provided superb service, and he did a little of everything around there. On site breakfast was very good. But none would have been possible without Mr. Kostas, we cannot thank him enough.
Superhost

Condo in Tholos
4.57 out of 5 average rating, 21 reviewsSuperior Suite with Plunge Pool @Aplada Suites
OliverRating, 5 stars9 months ago
A wonderful place to stay! It strikes the perfect balance of seclusion and accessibility, being just a short walk from Oia. The plunge pool offers incredible views of the sea, making the experience truly exceptional. Yiannis was incredibly helpful, assisting with our bags from the car to the accommodation and again during checkout. Nothing was too much trouble for him! His excellent recommendations for restaurants and activities greatly enhanced our time on Santorini.
Superhost

Condo in Exo Gonia
4.92 out of 5 average rating, 173 reviewsKarpimo Suites, Samarina House
JacquelineRating, 5 stars8 months ago
Coole Unterkunft, schneller Check in. Empfehlungen Restaurants vor Ort. Nette Betreiber. Kostenloser Parkplatz direkt gegenüber.
Guest favourite

Condo in Fira
4.9 out of 5 average rating, 121 reviewsGarden Aprtmnt 2p, Karterados Beach
ColyneRating, 5 stars7 months ago
Merci à Helen, qui nous a préparé de l’eau et des snacks car nous arrivions tard. Vraiment disponible, répond très rapidement. Le logement est propre et plus grand que ce qu’il en a l’air sur les photos. Tout est niquel
Superhost

Condo in Fira
5 out of 5 average rating, 3 reviewsBlue Apartment Eos Villa Imerovigli
MarcRating, 5 stars117 months ago
George was a great host and made us feel welcome right from the start. He sorted out our airport transfers, ATV hire etc as soon as we asked and also had great recommendations for what bars, restaurants we should try. The accommodation and the pool were great and spotless when we arrived and throughout, so I would most definitely recommend staying at Eos Villas as it's the perfect location on the island between all the main areas you'd want to visit anyway.

Condo in Fira
4.43 out of 5 average rating, 7 reviewsOffer!!! Cave Pool Villa
SarahRating, 5 stars32 months ago
We had an amazing stay at George’s place. The Villa was beautiful and close to everything. Staff was incredibly helpful and organized our activities/rides. We can’t wait to come back!
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