Top Vacation homes in Santorini Caldera

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

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22 Guests, 1 Room
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61-80 out of 91 vacation homes
From   US$ 441 /nightSelect
The Wesense Santorini Villa Imerovigli is set 5 minutes by car from MATI Art Gallery and within 300 metres of Anastasi Church.
6 adults
5 bedrooms
6 beds
From   US$ 1 184 /nightSelect
  • Private infinity pool with stunning views
  • Luxurious organic mattresses throughout villas
  • Heritage lime kiln incorporated into design
8.6
Great15 reviews
  • Hot Tub
  • Family Rooms
  • Coffee Shop
From   US$ 965 /nightSelect
  • Breathtaking sea views from balconies
  • On-site hot tub for relaxation
  • Family-friendly accommodations available
8.6
Great30 reviews
  • Heated Pool
  • Air Conditioning
  • Private Bathroom
From   US$ 579 /nightSelect
  • Heated outdoor pool with caldera views
  • Stylish, contemporary rooms with amenities
  • Arrangements for wine tasting tours
8.6
Great21 reviews
  • Infinity pool
  • On-site Spa
  • Private terraces
From   US$ 422 /nightSelect
  • Stunning caldera sunset views
  • Boutique suites with Cycladic decor
  • Exclusive helicopter transportation service
  • Private Pool
  • Hot Tub
  • Jacuzzi
From   US$ 229 /nightSelect
  • Private pool with sea views
  • On-site spa with diverse massages
  • Airport transfer and car rental services
Holiday home
  • Air conditioning
  • Streaming services
  • Car rental
From   US$ 260 /nightSelect
  • Sea-view accommodation with outdoor dining
  • Diving and fishing activities nearby
  • Concierge and housekeeping services available
8.6
Great34 reviews
  • Outdoor Jacuzzi
  • Rooftop Pool
  • Luxury Amenities
From   US$ 367 /nightSelect
  • Private outdoor Jacuzzi with stunning views
  • Luxurious suite carved from volcanic rock
  • Located near famous Oia sunsets
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
8.4
Great30 reviews
  • Private Pool
  • On-site Spa
  • Outdoor Dining
From   US$ 1 423 /nightSelect
  • Private villas with Aegean Sea views
  • Self-standing villas with private pools
  • On-site spa with hot tub and massages
From   US$ 1 424 /nightSelect
Set 15 minutes by car from Skaros, the Namaste Suites By Caldera Houses Oia features a private swimming pool and a continental breakfast.
From   US$ 368 /nightSelect
8.8
Great1 review
  • Hot tub
  • Patio
  • Family rooms
From   US$ 678 /nightSelect
  • Private hot tub with sea views
  • Air-conditioned units with kitchen
  • In-room breakfast with local specialties
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$ 128 /nightSelect
Being within 0.8 miles of Panagia Platsani, this villa features a sunny patio.
  • Private terrace
  • Steam bath
  • Outdoor Jacuzzi
From   US$ 865 /nightSelect
  • Private indoor heated pool
  • Intimate cave-like wine cellar
  • Serene adults-only atmosphere
  • Hot Tub
  • Coffee Shop
  • Diving Services
From   US$ 316 /nightSelect
  • Private hot tub in each unit
  • Secluded sea view terraces
  • On-site coffee shop
  • Outdoor Pool
  • Sea Views
  • Car Rental
From   US$ 1 418 /nightSelect
  • Villa with terrace and sea views
  • Seasonal outdoor swimming pool
  • On-site car rental service available
8.6
Great4 reviews
  • Heated Jacuzzi
  • Sun Terrace
  • Private Entrance
From   US$ 1 363 /nightSelect
  • Stunning sunset views over the caldera
  • Outdoor heated jacuzzi for relaxation
  • Bespoke breakfast prepared by local chef
From   US$ 1 670 /nightSelect