Top Vacation rentals in Santorini Caldera

Find the Top Vacation rentals in Santorini Caldera – 200+ Quality Options from Leading Providers

Destination
Where do you want to go?
Check-in
Select date
Check-out
Select date
Rooms & Guests
22 Guests, 1 Room
2Filter & Sort
61-80 out of 237 vacation rentals
2Filter & Sort
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
4 adults
1 bedroom
2 beds
From   US$ 229 /nightSelect
  • Private pool with sea views
  • On-site spa with diverse massages
  • Airport transfer and car rental services
2 adults
1 bedroom
1 bed
From   US$ 335 /nightSelect
  • Heated mini plunge pool with sea views
  • Tailor-made concierge services available
  • Authentic cave-house accommodation design
  • 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
From   US$ 477 /nightSelect
The Inspire Santorini Luxury Villas, located merely a 5-minute walk from Pelican Kipos, is also at a proximity to Cathedral of Saint John the Baptist.
Holiday home
  • Air conditioning
  • Streaming services
  • Car rental
From   US$ 186 /nightSelect
  • Sea-view accommodation with outdoor dining
  • Diving and fishing activities nearby
  • Concierge and housekeeping services available
  • Ocean views
  • Private terrace
  • Outdoor dining
From   US$ 170 /nightSelect
  • Private entrance with ocean views
  • Fully equipped kitchen facilities
  • Paid airport shuttle service available
  • Infinity Pool
  • On-site Spa
  • Private Terrace
From   US$ 732 /nightSelect
  • Private infinity pool with epic views
  • Luxurious Cycladic architecture and design
  • On-site spa with extensive treatments
  • Private terrace
  • Steam bath
  • Outdoor Jacuzzi
From   US$ 865 /nightSelect
  • Private indoor heated pool
  • Intimate cave-like wine cellar
  • Serene adults-only atmosphere
  • Private Pool
  • Outdoor Hot Tub
  • Luxury Spa
From   US$ 706 /nightSelect
  • Private villas with outdoor hot tubs
  • Spectacular views of Pyrgos Village
  • Luxurious spa and wellness services
  • Heated Jacuzzi
  • Sun Terrace
  • Private Entrance
From   US$ 1 020 /nightSelect
  • Stunning sunset views over the caldera
  • Outdoor heated jacuzzi for relaxation
  • Bespoke breakfast prepared by local chef
  • 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
  • Infinity Pool
  • Outdoor Hot Tubs
  • Hammam
From   US$ 1 241 /nightSelect
  • Infinity pools with stunning caldera views
  • Luxurious on-site spa treatments available
  • Elegant villa with five bedrooms
  • Hot tub
  • Private entrance
  • Bicycle rental
From   US$ 1 029 /nightSelect
  • Private hot tub with sea views
  • Four-bedroom villa for family stays
  • Outdoor dining area with quiet views
Holiday home
From   US$ 307 /nightSelect
The Casa Sigala Cave Villa is nestled in the Oia Caldera district, Oia Castle is 750 metres away.
Holiday home
  • Private Jacuzzi
  • Pool Bar
  • Fitness Room
From   US$ 230 /nightSelect
  • Suites with private outdoor jacuzzis
  • Outdoor pool with stunning sea views
  • A la carte Greek breakfast options
From   US$ 1 907 /nightSelect
The Wesense Santorini Villa Imerovigli is set 5 minutes by car from MATI Art Gallery and within 300 metres of Anastasi Church.
  • Hot Tub
  • Coffee Shop
  • Diving Services
From   US$ 493 /nightSelect
  • Private hot tub in each unit
  • Secluded sea view terraces
  • On-site coffee shop
From   US$ 318 /nightSelect
While staying at the Michelangelo Beach Villa you are invited to discover Sunset in Oia, set about 1.8 miles away, or Oia Castle, which is about 2 miles away.
From   US$ 125 /nightSelect
Nestled in a historical neighbourhood, the Lagadi Suites By K&K Mesaria is 1.3 miles from Castelli of Pyrgos.
  • Outdoor Pool
  • Sea Views
  • Car Rental
From   US$ 772 /nightSelect
  • Villa with terrace and sea views
  • Seasonal outdoor swimming pool
  • On-site car rental service available