Top Vacation rentals in Santorini Caldera

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

Destination
Where to?
Check-in
Select date
Check-out
Select date
Rooms & Guests
22 Guests, 1 Room
2Filter & Sort
61-80 out of 95 vacation rentals
9.0
Perfect5 reviews
10 adults
5 bedrooms
5 beds
From   US$ 623 /nightSelect
  • Infinity pools with stunning caldera views
  • Luxurious on-site spa treatments available
  • Elegant villa with five bedrooms
8.6
Great22 reviews
6 adults
2 bedrooms
3 beds
From   US$ 181 /nightSelect
Situated 1 miles from Orthodox Metropolitan Cathedral, this venue features a sun terrace and a sun deck.
Holiday home
8.2
Great26 reviews
  • Private Courtyards
  • Balconies
  • Garden
From   US$ 70 /nightSelect
  • Authentic Santorini winery conversion
  • Enchanting balconies with sea views
  • Private courtyards for relaxation
8.6
Great10 reviews
  • Private Villas
  • Hot Tub
  • Sun Terraces
From   US$ 475 /nightSelect
  • Private villas with hot tubs
  • On-site yoga and outdoor activities
  • Beautiful sea-view sun terraces
Holiday home
8.2
Great18 reviews
From   US$ 236 /nightSelect
The Casa Sigala Cave Villa is nestled in the Oia Caldera district, Oia Castle is 750 metres away.
  • Infinity pool
  • Private courtyard
  • Outdoor jacuzzi
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$ 801 /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
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$ 873 /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.
8.8
Great1 review
  • Hot tub
  • Patio
  • Family rooms
From   US$ 1 541 /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
  • Hot Tub
  • Coffee Shop
  • Diving Services
From   US$ 666 /nightSelect
  • Private hot tub in each unit
  • Secluded sea view terraces
  • On-site coffee shop
  • Heated Plunge Pool
  • Private Terrace
  • Luxury Amenities
From   US$ 670 /nightSelect
  • Heated mini plunge pool with sea views
  • Tailor-made concierge services available
  • Authentic cave-house accommodation design
From   US$ 1 670 /nightSelect
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.