Top Vacation homes in Santorini Caldera

Find the Top Vacation homes in Santorini Caldera – 100+ 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
1Filter & Sort
21-40 out of 150 vacation homes
1Filter & Sort
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
8.0
Great2 reviews
5 adults
2 bedrooms
3 beds
From   US$ 985 /nightSelect
  • Unobstructed views of the Caldera
  • Chic design with volcanic soil integration
  • Private pools for each villa
8.6
Great9 reviews
8 adults
3 bedrooms
4 beds
From   US$ 445 /nightSelect
  • Spectacular Caldera views from terraces
  • Private pool and hot tub in suites
  • On-site spa with beauty services
8.6
Great61 reviews
  • Hot Tub
  • Outdoor Pool
  • Concierge Service
From   US$ 259 /nightSelect
  • Private external hot tubs for relaxation
  • Elegant villas with romantic atmosphere
  • Seasonal outdoor swimming pool available
8.4
Great3 reviews
  • Furnished Terraces
  • Private Massage
  • Four-Poster Beds
From   US$ 371 /nightSelect
  • Stylish suites with sea and caldera views
  • American breakfast served in scenic settings
  • Exclusive massage treatments on private terraces
8.2
Great18 reviews
  • Outdoor furniture
  • Flat-screen TV
  • Private bathroom
From   US$ 646 /nightSelect
  • Breathtaking sea views from the villa
  • Air-conditioned units with private entrances
  • Outdoor dining area for guests
8.8
Great13 reviews
  • Swimming Pool
  • Private Parking
  • Picnic Area
From   US$ 557 /nightSelect
  • Stunning sea view accommodations
  • Outdoor swimming pool with sun loungers
  • On-site spa with various massage options
8.8
Great37 reviews
  • Sun terrace
  • Garden
  • Fully equipped kitchen
From   US$ 897 /nightSelect
  • Panoramic Aegean Sea views
  • Authentic Santorinian cave architecture
  • On-site water sport facilities
8.4
Great259 reviews
  • Air Conditioning
  • Satellite TV
  • Fridge
From   US$ 78 /nightSelect
  • Scenic sunset views from the hotel
  • Air-conditioned rooms with satellite TV
  • Short walk to Orthodox Church
8.6
Great37 reviews
  • Mountain views
  • Fully equipped kitchen
  • Outdoor dining area
From   US$ 291 /nightSelect
  • Panoramic sea view terrace
  • Private entrance for added privacy
  • Accessible hiking opportunities nearby
8.6
Great64 reviews
  • Natura Spa
  • Akau Restaurant
  • Infinity Pool
From   US$ 610 /nightSelect
  • Private heated plunge pool in villas
  • Nikkei cuisine at Akau Restaurant
  • Infinity pool with spectacular views
  • Private Pool
  • Spa Centre
  • Garden Area
From   US$ 950 /nightSelect
  • Private villa with outdoor swimming pool
  • Spa services including full body massage
  • Spacious terrace offering sea views
7.8
Very good6 reviews
  • Sea view terrace
  • Air conditioning
  • Self-catering kitchen
From   US$ 1 027 /nightSelect
  • Elegant villas with sea and volcano views
  • Centrally located near historical sites
  • On-site spa services available
8.6
Great10 reviews
  • Private Villas
  • Hot Tub
  • Sun Terraces
From   US$ 465 /nightSelect
  • Private villas with hot tubs
  • On-site yoga and outdoor activities
  • Beautiful sea-view sun terraces
  • Infinity Pool
  • Private Terrace
  • Concierge Service
From   US$ 1 517 /nightSelect
  • Breathtaking caldera view from private terrace
  • Infinity swimming pool overlooking Aegean Sea
  • Dedicated 24/7 concierge service available
8.6
Great10 reviews
  • 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
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
8.4
Great30 reviews
  • Private Pool
  • On-site Spa
  • Outdoor Dining
From   US$ 1 114 /nightSelect
  • Private villas with Aegean Sea views
  • Self-standing villas with private pools
  • On-site spa with hot tub and massages
From   US$ 781 /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
  • Cooking classes
  • Private terrace
From   US$ 968 /nightSelect
  • Private entrance with stunning sea views
  • Relaxing hot tub and on-site massage
  • Fully equipped kitchen for cooking classes
8.8
Great3 reviews
  • On-site Spa
  • Diving Activities
  • Beach Loungers
From   US$ 216 /nightSelect
  • On-site spa with massage services
  • Diverse activities including diving and snorkeling
  • Pool/beach towels and loungers provided