Top Vacation rentals in Santorini Caldera

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

Destination
Where to?
Check-in
Select date
Check-out
Select date
Rooms & Guests
22 Guests, 1 Room
2Filter & Sort
161-180 out of 230 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
2 bedrooms
3 beds
From   US$ 516 /nightSelect
  • Stunning sea views from all villas
  • Seasonal outdoor swimming pool
  • Diving and hiking activities available
2 adults
1 bedroom
2 beds
From   US$ 1 418 /nightSelect
  • Villa with terrace and sea views
  • Seasonal outdoor swimming pool
  • On-site car rental service available
  • 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
  • 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
Apartment
  • Hot tub
  • Balcony
  • Kitchenette
From   US$ 267 /nightSelect
  • Hot tub with stunning sea views
  • Private balcony for picturesque sunsets
  • Cultural walking tours available
Villa
  • Sea views
  • Diving activities
  • Private entrance
From   US$ 503 /nightSelect
  • Sea view terrace for relaxation
  • On-site diving activities available
  • Pet-friendly accommodations offered
  • Hot tub
  • Bicycle rental
  • Sun terrace
From   US$ 352 /nightSelect
  • Private balconies with scenic garden views
  • Relaxing hot tub and massage services
  • Bicycle rental for local exploration
  • Private Jacuzzi
  • Communal Pool
  • Spacious Villas
From   US$ 259 /nightSelect
  • Private jacuzzis in each villa
  • Locally sourced organic breakfast options
  • Eco-friendly design and practices
From   US$ 932 /nightSelect
Composed of 2 bedrooms and 2 bathrooms, this villa is set only 0.5 miles from Agios Georgios Church.
  • Hot Tubs
  • Sun Terrace
  • Car Rentals
From   US$ 180 /nightSelect
  • Private hot tubs in all villas
  • Beautiful sea views from accommodations
  • Complimentary welcome drink upon arrival
  • Outdoor hot tub
  • Spa centre
  • Garden views
From   US$ 201 /nightSelect
  • Individually decorated villas with hot tub
  • Daily homemade breakfast provided
  • On-site spa with various treatments
  • Sea views
  • On-site spa
  • Outdoor dining
From   US$ 817 /nightSelect
  • Sea view balcony for outdoor dining
  • On-site spa with comprehensive treatments
  • Adults-only for romantic getaways
Holiday home
  • Private terrace
  • Spa services
  • Outdoor dining
From   US$ 418 /nightSelect
  • On-site spa with diverse services
  • Private terrace in select units
  • Access to beach activities nearby
Holiday home
  • Sea views
  • Air conditioning
  • Flat-screen TV
From   US$ 169 /nightSelect
  • Sea-view holiday home with outdoor seating
  • Adults-only accommodation for relaxed stays
  • Activities like diving and cycling nearby
From   US$ 259 /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.
  • Private pool
  • Outdoor dining
  • On-site spa
From   US$ 897 /nightSelect
  • Private villas with Aegean Sea views
  • Luxurious cycladic-style accommodations
  • On-site spa with diverse massage options
From   US$ 466 /nightSelect
Staying at the Villa Ioli Anastasia Firostefani means you will be 0.3 miles from Timios Stavros, while enjoying a private swimming pool onsite.
  • Hot tub
  • Fireplace
  • Outdoor dining
From   US$ 402 /nightSelect
  • Panoramic volcano and Aegean sea views
  • Private balcony with hot tub
  • On-site water sports facilities
Apartment
  • Hot tub
  • Fitness room
  • Private balcony
From   US$ 809 /nightSelect
  • Mountain-view terrace with jacuzzi
  • On-site spa with beauty treatments
  • Daily yoga and fitness classes
  • Private Infinity
  • Spa Treatments
  • Helicopter Transfers
From   US$ 417 /nightSelect
  • Villas with private infinity pools
  • Spa with extensive treatment options
  • Helicopter transfers and tours available