Top Holiday rentals in Santorini Caldera

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

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Rooms & Guests
22 Guests, 1 Room
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41-60 out of 92 holiday rentals
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Holiday home
4 adults
2 bedrooms
2 beds
From   US$ 324 /nightSelect
  • Stunning sea views from private terrace
  • Fully equipped kitchen in select units
  • Air-conditioned, comfortable holiday homes
4 adults
2 bedrooms
2 beds
From   US$ 240 /nightSelect
  • Stunning sea view balconies available
  • Air-conditioned apartments with modern amenities
  • On-site car rental service offered
Apartment
  • Outdoor jacuzzi
  • Elegant cafe
  • Spa services
From   US$ 923 /nightSelect
  • Private outdoor jacuzzi with Caldera views
  • Spectacular sunset views from private spaces
  • Elegant cafe with Caldera view
  • Infinity Pool
  • Private Balconies
  • Gourmet Restaurant
From   US$ 571 /nightSelect
  • Breathtaking sunset viewing private balconies
  • Infinity pool with spectacular caldera views
  • Culinary delights with scenic restaurant views
  • Heated Pool
  • Spa Services
  • Outdoor Fireplace
From   US$ 197 /nightSelect
  • Cave suite with heated plunge pool
  • Panoramic caldera and sunset views
  • On-site spa and beauty treatments
  • Sun terrace
  • Spa services
  • Outdoor dining
From   US$ 301 /nightSelect
  • Aegean Sea and Caldera views
  • Traditionally decorated two-level suites
  • On-site horseback riding activities
Apartment
  • Outdoor Jacuzzi
  • Sea-view pool
  • Private verandas
From   US$ 502 /nightSelect
  • Breathtaking caldera view from private verandas
  • Luxurious suites with outdoor Jacuzzis
  • Concierge services for personalized experiences
  • Private balcony
  • Air conditioning
  • Jacuzzi
From   US$ 444 /nightSelect
  • Sea-view rooms with private balconies
  • Adults-only environment for tranquility
  • On-site car rental service available
  • Family rooms
  • Sea views
  • Paid shuttle
From   US$ 227 /nightSelect
  • Sea view terraces for relaxation
  • Family rooms with modern amenities
  • Paid airport shuttle service available
Apartment
  • Heated pool
  • Private parking
  • Picnic area
From   US$ 442 /nightSelect
  • Stunning sea views from every unit
  • Heated swimming pool available for guests
  • In-room breakfast options for convenience
  • Air Conditioning
  • Private Bathroom
  • Car Rental
From   US$ 181 /nightSelect
  • Fully equipped kitchen with dining area
  • Scenic terrace with sea views
  • On-site massage services available
  • Hot Tub
  • Family Rooms
  • Private Patio
From   US$ 978 /nightSelect
  • Private hot tub in each unit
  • Stunning sea view accommodations
  • Continental and vegetarian breakfast
  • Private Hot Tub
  • Sea-view Balcony
  • In-room Breakfast
From   US$ 293 /nightSelect
  • Sea-view balconies for stunning sunsets
  • Private hot tubs in each unit
  • On-site massage services available
Apartment
  • Infinity Pool
  • On-site Spa
  • Continental Breakfast
From   US$ 121 /nightSelect
  • Stunning Aegean Sea views from balconies
  • Family-run with personalized excursion services
  • On-site spa offering diverse treatments
  • Private Hot Tub
  • Outdoor Terrace
  • Kitchenette
From   US$ 217 /nightSelect
  • Stunning Caldera sunset views
  • Private hot tubs with sea view
  • Romantic cave houses with artistic design
  • Private Hot Tub
  • Concierge Service
  • Luxury Amenities
From   US$ 1 433 /nightSelect
  • Breathtaking caldera views from every villa
  • Private outdoor hot tubs in each villa
  • Exclusive venue for weddings and events
  • Outdoor Pool
  • Massage Spa
  • Furnished Terraces
From   US$ 449 /nightSelect
  • Aegean Sea views from furnished terraces
  • Outdoor pool with sun loungers
  • On-site massage spa services
  • Heated Jacuzzi
  • Private Balcony
  • Plunge Pool
From   US$ 295 /nightSelect
  • Stunning caldera views from every suite
  • Private heated Jacuzzis in suites
  • Luxurious spa services on-site
  • Hot tub
  • Espresso machine
  • Daily maid service
From   US$ 720 /nightSelect
  • Cave-style accommodation with breathtaking views
  • Private hot tubs in all units
  • Homemade breakfast on private veranda
Apartment
  • Private terraces
  • Outdoor dining
  • Adult-only setting
From   US$ 442 /nightSelect
  • Stunning Caldera and volcano views
  • Traditional Santorinian-style accommodations
  • Relaxing on-site spa services