The 30 Best Holiday Rentals in Santorini Caldera

Ranked 1 out of 772 in the region, as well as being 1 of 259 for holiday rentals in Oia.

• “Olvos was absolutely stunning and magical in every way!”
• “Instagram worthy property with the service to match!”
• “Paradise”
• See more reviews of Olvos Luxury Suites

Ranked 2 out of 772 in the region, as well as being 1 of 41 for holiday rentals in Firostefani.

• “The most breathtaking view that you can have, avoid seeing...”
• “Excellent value in a great location with wonderful views.”
• “Spectacular view”
• See more reviews of Santorini View Studios - Firostefani Caldera

Ranked 3 out of 772 in the region, as well as being 1 of 211 for holiday rentals in Fira.

• “BEAUTIFUL SUITE RECOMMENDED”
• “Fantastic place!”
• “I would definitely recommend this place to my friends.”
• See more reviews of Deep in cave suites

Ranked 4 out of 772 in the region, as well as being 2 of 259 for holiday rentals in Oia.

• “Very private and still very close to Oia (2min drive /10...”
• “Relaxing oasis in Oia”
• “Easily the best villa we’ve ever stayed at! The location was great - private yet within walking distance of everything a”
• See more reviews of Saint John Oia-Private Heated Pool Villas

Ranked 5 out of 772 in the region, as well as being 3 of 259 for holiday rentals in Oia.

• “Perfect stay in Santorini!!”
• “Great place to stay”
• “Great place!”
• See more reviews of Hyperion Oia Suites

Ranked 6 out of 772 in the region, as well as being 1 of 106 for holiday rentals in Imerovigli.

• “It was an amazing vacation, most of it because of the amazing suite that we had with fantastic view and great hospitalit”
• “Amazing and I will be back one day.”
• “Beyond expectations. Just amazing and highly recommended”
• See more reviews of Avista Suites

Ranked 7 out of 772 in the region, as well as being 2 of 106 for holiday rentals in Imerovigli.

• “We loved it.”
• “I have visited a few Greek islands including Crete, Rhodes, Kefalonia, Kos, Lefkada and Zakhyntosbut I never received a”
• “Great option if you want a luxe and private stay”
• See more reviews of Bianco Diverso Suites

Ranked 8 out of 772 in the region, as well as being 3 of 106 for holiday rentals in Imerovigli.

• “GO FOR IT!”
• “Grate place we will back for sure”
• “Absolutely fantastic.”
• See more reviews of Lithi Luxury Retreat

Ranked 9 out of 772 in the region, as well as being 4 of 259 for holiday rentals in Oia.

• “A great location and a wonderful host”
• “Best place in Oia. Everything perfect!”
• “Amazing place to stay and have the experience!”
• See more reviews of Anemi House & Villas

Ranked 10 out of 772 in the region, as well as being 2 of 211 for holiday rentals in Fira.

• “Loved our stay, good value for money & will definitely be back!”
• “We loved your stay, the team of Thinari Lodge is excellent and they always made us feel like home.”
• “.”
• See more reviews of Thimari Lodge

Ranked 11 out of 772 in the region, as well as being 5 of 259 for holiday rentals in Oia.

• “Lovely Brand New Villas”
• “We like everything about the facilities.”
• “Comfortable luxury near Santorini’s most romantic and beautiful coastline.”
• See more reviews of Oia Kissiri - private pool villas

Ranked 12 out of 772 in the region, as well as being 3 of 211 for holiday rentals in Fira.

• “The host (Yiannis) was very warm and welcoming and we raised...”
• “Excellent view and friendly staff!”
• “If we could give a rating of 11, we would....”
• See more reviews of Numa Santorini

Ranked 13 out of 772 in the region, as well as being 4 of 211 for holiday rentals in Fira.

• “The most amazing place to stay”
• “Breathtaking view”
• “Everything!”
• See more reviews of Fira Deep Blue Suites

Ranked 14 out of 772 in the region, as well as being 4 of 106 for holiday rentals in Imerovigli.

• “Priceless View, Outstanding Service and Breakfast!”
• “Vacations to Paradise”
• “The best stay in Santorini”
• See more reviews of Atoles Retreat

Ranked 15 out of 772 in the region, as well as being 5 of 106 for holiday rentals in Imerovigli.

• “Me and my husband booked Eteoro suites after a bit of...”
• “Perfection in Santorini”
• “Stunning! Amazing Eteoro Suites!”
• See more reviews of Eteoro Suites

Ranked 16 out of 772 in the region, as well as being 5 of 211 for holiday rentals in Fira.

• “Amor Hideaway Villas So Good We Love It”
• “Great location , Stamatis was a great host and very helpful and accommodating. The staff was all very nice the place was”
• “The staff were amazing, villas were so clean, unique and quite mind blowing, we always had everything we needed. Thanks”
• See more reviews of Amor Hideaway Villas

Ranked 17 out of 772 in the region, as well as being 6 of 259 for holiday rentals in Oia.

• “2 night stay in early April”
• “Gorgeous views, we didn't want to leave! Elisabeth is the best host- helpful and generous. Worth it!”
• “So relaxing with the best view”
• See more reviews of Blessed Blue Boutique Cave Suite

Ranked 18 out of 772 in the region, as well as being 7 of 259 for holiday rentals in Oia.

• “The location is nice and view is not so great . If yoy just want to relax with immediate access to the shopping street,”
• “every thing is perfect”
• “Fairy-tale !!”
• See more reviews of Alisaris Cave Suites

Ranked 19 out of 772 in the region, as well as being 8 of 259 for holiday rentals in Oia.

• “muy bien ubicado, en el corazón de Oia, muchas cosas cerca,...”
• “Very good stay and enjoyed ourselves”
• “Best hotel we had in Greece.”
• See more reviews of Delta Suites

Ranked 20 out of 772 in the region, as well as being 6 of 211 for holiday rentals in Fira.

• “Once in a lifetime dreamy experience”
• “Exceeded our expectations! So gorgeous and authentic. Relaxing, elegant, and rich!”
• “Relaxing stay in Fira”
• See more reviews of Palmariva Villas

Ranked 21 out of 772 in the region, as well as being 6 of 106 for holiday rentals in Imerovigli.

• “Αξέχαστη διαμονή!”
• “Absolute bliss”
• “It’s Heaven n Such a lovely retreat”
• See more reviews of Mardanza Exclusive

Ranked 22 out of 772 in the region, as well as being 1 of 62 for holiday rentals in Akrotiri.

• “Exceptional”
• “Matthew is a consummate and gracious host. He took care of everything, had wonderful suggestions and ensured we had a f”
• “This was an incredible experience.”
• See more reviews of Vineyard Exclusive Suites

Ranked 23 out of 772 in the region, as well as being 7 of 211 for holiday rentals in Fira.

• “Fab stay at Fanari Vista Suites”
• “”
• “Exceptional property with unparalleled view of Caldera”
• See more reviews of Fanari Vista Suites

Ranked 24 out of 772 in the region, as well as being 8 of 211 for holiday rentals in Fira.

• “Absolutely perfect stay in many ways.”
• “Beautiful and friendly.”
• “The hospitality received from Chrisa and the rest of the...”
• See more reviews of Enigma Suites

Ranked 25 out of 772 in the region, as well as being 9 of 211 for holiday rentals in Fira.

• “Excellent location and view.”
• “Everything about White Ark is first class.”
• “paradise”
• See more reviews of White Ark

Ranked 26 out of 772 in the region, as well as being 9 of 259 for holiday rentals in Oia.

• “Sublime”
• “Amazing place and location. Chris could not do more!!”
• “Better than expected”
• See more reviews of White Side Suites

Ranked 27 out of 772 in the region, as well as being 2 of 62 for holiday rentals in Akrotiri.

• “Amazing villa, breathtaking views, great location and lovely hosts. We would warmly recommend and hope to visit again so”
• “Come here if you want to unwind and spend quality time in the lap of nature with style!”
• “Awesome”
• See more reviews of Summer Lovers Villa

Ranked 28 out of 772 in the region, as well as being 10 of 211 for holiday rentals in Fira.

• “Amazing villa.”
• “I would definitely recommend this place to anyone looking for a stay in Fira!”
• “Beautiful villa with amazing view. Antonios was very helpful and provided great suggestions and helped book excursions o”
• See more reviews of NK Cave House Villa

Ranked 29 out of 772 in the region, as well as being 7 of 106 for holiday rentals in Imerovigli.

• “In een woord “GEWELDIG “”
• “The apartment had a great view over the Caldera but was not...”
• “The service and location were exceptional.”
• See more reviews of Vallais Villa

Ranked 30 out of 772 in the region, as well as being 10 of 259 for holiday rentals in Oia.

• “Excellent option to stay in Amalfi Coast, very nice facilities and room, excellent hosts”
• “Kind staff, very clean and well laid out.”
• “Best location!”
• See more reviews of Aris Caves