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
21-40 out of 95 vacation rentals
Holiday home
8.6
Great27 reviews
From   US$ 329 /nightSelect
  • Hot tub and massage services available
  • Private balconies with sea views
  • Fully equipped kitchenette in suites
Holiday home
8.6
Great39 reviews
4 adults
1 bedroom
2 beds
From   US$ 121 /nightSelect
  • Suites with private outdoor jacuzzis
  • Outdoor pool with stunning sea views
  • A la carte Greek breakfast options
8.6
Great37 reviews
  • Mountain views
  • Fully equipped kitchen
  • Outdoor dining area
From   US$ 295 /nightSelect
  • Panoramic sea view terrace
  • Private entrance for added privacy
  • Accessible hiking opportunities nearby
  • Private Pool
  • Spa Centre
  • Garden Area
From   US$ 2 449 /nightSelect
  • Private villa with outdoor swimming pool
  • Spa services including full body massage
  • Spacious terrace offering sea views
From   US$ 1 079 /nightSelect
Composed of 2 bedrooms and 2 bathrooms, this villa is set only 0.5 miles from Agios Georgios Church.
  • Hot tub
  • Sea views
  • Concierge service
From   US$ 613 /nightSelect
  • Private hot tub with sea views
  • Continental breakfast served in-room
  • Concierge service for local activities
8.6
Great27 reviews
  • Outdoor hot tub
  • Sea-view terrace
  • In-room breakfast
From   US$ 441 /nightSelect
  • Stunning sea-view terrace with hot tub
  • Adults-only property for exclusive tranquility
  • Private outdoor dining area available
  • Swimming Pool
  • Private Parking
  • Picnic Area
From   US$ 363 /nightSelect
  • Stunning sea view accommodations
  • Outdoor swimming pool with sun loungers
  • On-site spa with various massage options
  • Hot tub
  • Parking
  • Kitchenette
From   US$ 320 /nightSelect
  • Panoramic caldera sea views
  • Private hot tub for relaxation
  • Complimentary in-room breakfast
  • Heated Pool
  • Private Jacuzzi
  • Outdoor Terrace
From   US$ 3 525 /nightSelect
  • Private heated pool with stunning views
  • Exclusive concierge services for tailored experiences
  • Luxury terrace for intimate events
  • Infinity Pool
  • Private Terrace
  • Concierge Service
From   US$ 2 321 /nightSelect
  • Breathtaking caldera view from private terrace
  • Infinity swimming pool overlooking Aegean Sea
  • Dedicated 24/7 concierge service available
8.6
Great64 reviews
  • Natura Spa
  • Akau Restaurant
  • Infinity Pool
From   US$ 707 /nightSelect
  • Private heated plunge pool in villas
  • Nikkei cuisine at Akau Restaurant
  • Infinity pool with spectacular views
7.8
Very good6 reviews
  • Sea view terrace
  • Air conditioning
  • Self-catering kitchen
From   US$ 960 /nightSelect
  • Elegant villas with sea and volcano views
  • Centrally located near historical sites
  • On-site spa services available
Holiday home
8.4
Great46 reviews
  • Sun Loungers
  • Flat-Screen TV
  • Well-Equipped Kitchenette
From   US$ 162 /nightSelect
  • Panoramic Aegean Sea views
  • Traditionally-built cave apartments
  • Outdoor terraces with sun loungers
8.8
Great8 reviews
  • Hot Tub
  • Private Terraces
  • Wellness Spa
From   US$ 1 286 /nightSelect
  • Private hot tubs in all accommodations
  • Scenic mountain view terraces available
  • On-site wellness spa services offered
8.2
Great18 reviews
  • Outdoor furniture
  • Flat-screen TV
  • Private bathroom
From   US$ 1 310 /nightSelect
  • Breathtaking sea views from the villa
  • Air-conditioned units with private entrances
  • Outdoor dining area for guests
  • Hot tub
  • BBQ area
  • Table tennis
From   US$ 512 /nightSelect
  • Aegean Sea and caldera views
  • Outdoor hot tub for relaxation
  • Table tennis for entertainment
8.6
Great36 reviews
  • Shared Pool
  • Air Conditioning
  • Seating Area
From   US$ 225 /nightSelect
  • Aegean Sea views from private balconies
  • Outdoor pool with sun loungers
  • On-site spa with massage services
8.2
Great14 reviews
  • Private Verandas
  • In-room Spa
  • Custom Dining
From   US$ 296 /nightSelect
  • Breathtaking Caldera views from private verandas
  • Luxury spa services available in-villa
  • Custom food baskets and fine wine offerings