Top Vacation rentals in Santorini Caldera

Find the Top Vacation rentals in Santorini Caldera – 90+ Quality Options from Leading Providers

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22 Guests, 1 Room
2Filter & Sort
81-97 out of 97 vacation rentals
Holiday home
8.2
Great26 reviews
18 adults
6 bedrooms
10 beds
From   US$ 70 /nightSelect
  • Authentic Santorini winery conversion
  • Enchanting balconies with sea views
  • Private courtyards for relaxation
8.6
Great30 reviews
6 adults
3 bedrooms
4 beds
From   US$ 579 /nightSelect
  • Heated outdoor pool with caldera views
  • Stylish, contemporary rooms with amenities
  • Arrangements for wine tasting tours
8.2
Great47 reviews
  • Private Jacuzzi
  • Communal Pool
  • Spacious Villas
From   US$ 250 /nightSelect
  • Private jacuzzis in each villa
  • Locally sourced organic breakfast options
  • Eco-friendly design and practices
From   US$ 127 /nightSelect
Being within 0.8 miles of Panagia Platsani, this villa features a sunny patio.
Villa
8.4
Great17 reviews
  • Outdoor pool
  • Wellness packages
  • Private terrace
From   US$ 745 /nightSelect
  • Outdoor pool with sea views
  • Wellness packages for rejuvenation
  • Adults-only tranquil environment
From   US$ 1 670 /nightSelect
  • Heated Plunge Pool
  • Private Terrace
  • Luxury Amenities
From   US$ 353 /nightSelect
  • Heated mini plunge pool with sea views
  • Tailor-made concierge services available
  • Authentic cave-house accommodation design
Holiday home
9.0
Perfect6 reviews
From   US$ 394 /nightSelect
Featuring the vicinity to the Aegean Sea, this property with a full kitchen is in an area where guests can engage in such activities as canoeing, hiking and horseback riding.
Holiday home
8.2
Great18 reviews
From   US$ 236 /nightSelect
Situated 250 metres from Agios Georgios Church, the property provides accommodation with a sunbathing terrace and a picnic area.
8.6
Great34 reviews
  • Private Pool
  • Outdoor Hot Tub
  • Luxury Spa
From   US$ 800 /nightSelect
  • Private villas with outdoor hot tubs
  • Spectacular views of Pyrgos Village
  • Luxurious spa and wellness services
8.0
Great2 reviews
  • Private Pools
  • On-site Spa
  • Outdoor Dining
From   US$ 994 /nightSelect
  • Unobstructed views of the Caldera
  • Chic design with volcanic soil integration
  • Private pools for each villa
From   US$ 409 /nightSelect
  • Hot Tub
  • Spa Services
  • Outdoor Dining
From   US$ 897 /nightSelect
  • Stunning sea view terrace
  • Private hot tub and spa services
  • Outdoor dining with city views
Holiday home
From   US$ 399 /nightSelect
While staying at the Esmi Suites Santorini you are invited to discover Sunset in Oia, set 15 minutes away by car, or Orthodox Metropolitan Cathedral, which is a 5-minute ride away.
From   US$ 368 /nightSelect
Holiday home
  • Sea views
  • Air conditioning
  • Flat-screen TV
From   US$ 169 /nightSelect
  • Sea-view holiday home with outdoor seating
  • Adults-only accommodation for relaxed stays
  • Activities like diving and cycling nearby
  • Hot tub
  • Private entrance
  • Bicycle rental
From   US$ 415 /nightSelect
  • Private hot tub with sea views
  • Four-bedroom villa for family stays
  • Outdoor dining area with quiet views