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Oia Luxury Rentals

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394 rentals in Oia.
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Lioyerma Windmill Apt & Pool, vacation rental in Oia
Lioyerma Windmill Apt & Pool, vacation rental in Oia
Lioyerma Windmill Apt & Pool, vacation rental in Oia

Lioyerma Windmill Apt & Pool

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Unique 1868 Winery Canava - Caldera View, Private Pool, Hot tub, Sunbathing deck, vacation rental in Oia
Unique 1868 Winery Canava - Caldera View, Private Pool, Hot tub, Sunbathing deck, vacation rental in Oia
Unique 1868 Winery Canava - Caldera View, Private Pool, Hot tub, Sunbathing deck, vacation rental in Oia

Unique 1868 Winery Canava - Caldera View, Private Pool, Hot tub, Sunbathing deck

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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3 bedroom villa with private plunge pool, vacation rental in Oia
3 bedroom villa with private plunge pool, vacation rental in Oia
3 bedroom villa with private plunge pool, vacation rental in Oia

3 bedroom villa with private plunge pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Diamond Rock Venue - Weddings, vacation rental in Oia
The Diamond Rock Venue - Weddings, vacation rental in Oia
The Diamond Rock Venue - Weddings, vacation rental in Oia

The Diamond Rock Venue - Weddings

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Unique Restored 1868 Wine Canava - Caldera View, Private Pool, Sunbathing Deck, vacation rental in Oia
Unique Restored 1868 Wine Canava - Caldera View, Private Pool, Sunbathing Deck, vacation rental in Oia
Unique Restored 1868 Wine Canava - Caldera View, Private Pool, Sunbathing Deck, vacation rental in Oia

Unique Restored 1868 Wine Canava - Caldera View, Private Pool, Sunbathing Deck

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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SantoriniParadise: BLUE & WHITE cave house, authentic experience, Caldera view, vacation rental in Oia
SantoriniParadise: BLUE & WHITE cave house, authentic experience, Caldera view, vacation rental in Oia
SantoriniParadise: BLUE & WHITE cave house, authentic experience, Caldera view, vacation rental in Oia

SantoriniParadise: BLUE & WHITE cave house, authentic experience, Caldera view

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Elegant Luxurious Villa with a Breathtaking View, vacation rental in Oia
Elegant Luxurious Villa with a Breathtaking View, vacation rental in Oia
Elegant Luxurious Villa with a Breathtaking View, vacation rental in Oia

Elegant Luxurious Villa with a Breathtaking View

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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SantoriniParadise: PARADISE, outdoor Hot Tub, Caldera panorama!, vacation rental in Oia
SantoriniParadise: PARADISE, outdoor Hot Tub, Caldera panorama!, vacation rental in Oia
SantoriniParadise: PARADISE, outdoor Hot Tub, Caldera panorama!, vacation rental in Oia

SantoriniParadise: PARADISE, outdoor Hot Tub, Caldera panorama!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Twin Cave House - Oia, vacation rental in Oia
Twin Cave House - Oia, vacation rental in Oia
Twin Cave House - Oia, vacation rental in Oia

Twin Cave House - Oia

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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SantoriniParadise: PARADISE cave house, indoor winery & outdoor hot tub, Caldera, vacation rental in Oia
SantoriniParadise: PARADISE cave house, indoor winery & outdoor hot tub, Caldera, vacation rental in Oia
SantoriniParadise: PARADISE cave house, indoor winery & outdoor hot tub, Caldera, vacation rental in Oia

SantoriniParadise: PARADISE cave house, indoor winery & outdoor hot tub, Caldera

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Rose's Cave, vacation rental in Oia
Rose's Cave, vacation rental in Oia
Rose's Cave, vacation rental in Oia

Rose's Cave

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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SantoriniParadise: BLUE & WHITE Cave House, Santorini, Oia + hot tub!, vacation rental in Oia
SantoriniParadise: BLUE & WHITE Cave House, Santorini, Oia + hot tub!, vacation rental in Oia
SantoriniParadise: BLUE & WHITE Cave House, Santorini, Oia + hot tub!, vacation rental in Oia

SantoriniParadise: BLUE & WHITE Cave House, Santorini, Oia + hot tub!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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AQUA TERRA SUPERIOR PRIVATE VILLA  hot plunge pool  and sea view, vacation rental in Oia
AQUA TERRA SUPERIOR PRIVATE VILLA  hot plunge pool  and sea view, vacation rental in Oia
AQUA TERRA SUPERIOR PRIVATE VILLA  hot plunge pool  and sea view, vacation rental in Oia

AQUA TERRA SUPERIOR PRIVATE VILLA hot plunge pool and sea view

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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SantoriniParadise: HELIOS cave house, amazing sunset view , vacation rental in Oia
SantoriniParadise: HELIOS cave house, amazing sunset view , vacation rental in Oia
SantoriniParadise: HELIOS cave house, amazing sunset view , vacation rental in Oia

SantoriniParadise: HELIOS cave house, amazing sunset view

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Brandnew! Recently renovated from scratch with original greek island style!, vacation rental in Oia
Brandnew! Recently renovated from scratch with original greek island style!, vacation rental in Oia
Brandnew! Recently renovated from scratch with original greek island style!, vacation rental in Oia

Brandnew! Recently renovated from scratch with original greek island style!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Breathtaking Caldera View, Great Comfort, Romantic And Fully Revamped., vacation rental in Oia
Breathtaking Caldera View, Great Comfort, Romantic And Fully Revamped., vacation rental in Oia
Breathtaking Caldera View, Great Comfort, Romantic And Fully Revamped., vacation rental in Oia

Breathtaking Caldera View, Great Comfort, Romantic And Fully Revamped.

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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SantoriniParadise: HELIOS villa, amazing sunset views, perfect dream vacation!, vacation rental in Oia
SantoriniParadise: HELIOS villa, amazing sunset views, perfect dream vacation!, vacation rental in Oia
SantoriniParadise: HELIOS villa, amazing sunset views, perfect dream vacation!, vacation rental in Oia

SantoriniParadise: HELIOS villa, amazing sunset views, perfect dream vacation!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Wineryhouse where dreams live......, vacation rental in Oia
Wineryhouse where dreams live......, vacation rental in Oia
Wineryhouse where dreams live......, vacation rental in Oia

Wineryhouse where dreams live......

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Aqua & Terra cave house sea view  hot plunge pool, vacation rental in Oia
Aqua & Terra cave house sea view  hot plunge pool, vacation rental in Oia
Aqua & Terra cave house sea view  hot plunge pool, vacation rental in Oia

Aqua & Terra cave house sea view hot plunge pool

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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SantoriniParadise: SUNSET APARTMENT, panoramic Sunset view from rooftop terrace, vacation rental in Oia
SantoriniParadise: SUNSET APARTMENT, panoramic Sunset view from rooftop terrace, vacation rental in Oia
SantoriniParadise: SUNSET APARTMENT, panoramic Sunset view from rooftop terrace, vacation rental in Oia

SantoriniParadise: SUNSET APARTMENT, panoramic Sunset view from rooftop terrace

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Aerie beautiful house, heart of Oia's traditional settlement, Caldera view, vacation rental in Oia
Aerie beautiful house, heart of Oia's traditional settlement, Caldera view, vacation rental in Oia
Aerie beautiful house, heart of Oia's traditional settlement, Caldera view, vacation rental in Oia

Aerie beautiful house, heart of Oia's traditional settlement, Caldera view

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Traditional villa, 3 bedrooms, big living area, romantic view, bathroom+WC, vacation rental in Oia
Traditional villa, 3 bedrooms, big living area, romantic view, bathroom+WC, vacation rental in Oia
Traditional villa, 3 bedrooms, big living area, romantic view, bathroom+WC, vacation rental in Oia

Traditional villa, 3 bedrooms, big living area, romantic view, bathroom+WC

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lydia's House - indoor heated splash pool, Caldera view, vacation rental in Oia
Lydia's House - indoor heated splash pool, Caldera view, vacation rental in Oia
Lydia's House - indoor heated splash pool, Caldera view, vacation rental in Oia

Lydia's House - indoor heated splash pool, Caldera view

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blu Blanco Cave House, vacation rental in Oia
Blu Blanco Cave House, vacation rental in Oia
Blu Blanco Cave House, vacation rental in Oia

Blu Blanco Cave House

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BLUEDOME CAVEHOUSE OIA SANTORINI, vacation rental in Oia
BLUEDOME CAVEHOUSE OIA SANTORINI, vacation rental in Oia
BLUEDOME CAVEHOUSE OIA SANTORINI, vacation rental in Oia

BLUEDOME CAVEHOUSE OIA SANTORINI

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Traditional villa in Oia with Jacuzzi and unique view of the Volcano and Caldera, vacation rental in Oia
Traditional villa in Oia with Jacuzzi and unique view of the Volcano and Caldera, vacation rental in Oia
Traditional villa in Oia with Jacuzzi and unique view of the Volcano and Caldera, vacation rental in Oia

Traditional villa in Oia with Jacuzzi and unique view of the Volcano and Caldera

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Santo  Blue Horizon ( Blue domes ), vacation rental in Oia
Santo  Blue Horizon ( Blue domes ), vacation rental in Oia
Santo  Blue Horizon ( Blue domes ), vacation rental in Oia

Santo Blue Horizon ( Blue domes )

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Luxury 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly, vacation rental in Oia
Luxury 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly, vacation rental in Oia
Luxury 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly, vacation rental in Oia

Luxury 2 Bedroom Villa with outdoor Plunge Pool & Sea View, family friendly

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Villa in Oia, Santorini, vacation rental in Oia
Luxury Villa in Oia, Santorini, vacation rental in Oia
Luxury Villa in Oia, Santorini, vacation rental in Oia

Luxury Villa in Oia, Santorini

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Incredible caldera views! Full sunset, private, spacious - in the heart of Oia, vacation rental in Oia
Incredible caldera views! Full sunset, private, spacious - in the heart of Oia, vacation rental in Oia
Incredible caldera views! Full sunset, private, spacious - in the heart of Oia, vacation rental in Oia

Incredible caldera views! Full sunset, private, spacious - in the heart of Oia

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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House of the singing birds

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Astrea Suites: Cave Villa Valente, vacation rental in Oia
Astrea Suites: Cave Villa Valente, vacation rental in Oia
Astrea Suites: Cave Villa Valente, vacation rental in Oia

Astrea Suites: Cave Villa Valente

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stunning Caldera View With Jacuzzi In A Fully Renovated Cute Little Cave House!, vacation rental in Oia
Stunning Caldera View With Jacuzzi In A Fully Renovated Cute Little Cave House!, vacation rental in Oia
Stunning Caldera View With Jacuzzi In A Fully Renovated Cute Little Cave House!, vacation rental in Oia

Stunning Caldera View With Jacuzzi In A Fully Renovated Cute Little Cave House!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Blessed Blue boutique cave suite, vacation rental in Oia
Blessed Blue boutique cave suite, vacation rental in Oia
Blessed Blue boutique cave suite, vacation rental in Oia

Blessed Blue boutique cave suite

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Evmenia Luxury Cave Villa, vacation rental in Oia
Evmenia Luxury Cave Villa, vacation rental in Oia
Evmenia Luxury Cave Villa, vacation rental in Oia

Evmenia Luxury Cave Villa

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Luxury Villa at Oia with amazing view and  pool, vacation rental in Oia
Luxury Villa at Oia with amazing view and  pool, vacation rental in Oia
Luxury Villa at Oia with amazing view and  pool, vacation rental in Oia

Luxury Villa at Oia with amazing view and pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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270 Oia's View Cavehouse VII private swimming pool, sunset view, vacation rental in Oia
270 Oia's View Cavehouse VII private swimming pool, sunset view, vacation rental in Oia
270 Oia's View Cavehouse VII private swimming pool, sunset view, vacation rental in Oia

270 Oia's View Cavehouse VII private swimming pool, sunset view

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Pina Caldera Residence with Pool, vacation rental in Oia
Pina Caldera Residence with Pool, vacation rental in Oia
Pina Caldera Residence with Pool, vacation rental in Oia

Pina Caldera Residence with Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The house of the seven ships, vacation rental in Oia
The house of the seven ships, vacation rental in Oia

The house of the seven ships

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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270 Oia's View House III, private swimming pool, Sunset view, vacation rental in Oia
270 Oia's View House III, private swimming pool, Sunset view, vacation rental in Oia
270 Oia's View House III, private swimming pool, Sunset view, vacation rental in Oia

270 Oia's View House III, private swimming pool, Sunset view

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Ftelari Villa, vacation rental in Oia
Ftelari Villa, vacation rental in Oia
Ftelari Villa, vacation rental in Oia

Ftelari Villa

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Swinging Sunset Villa - Private Pool & Private Spa, vacation rental in Oia
Swinging Sunset Villa - Private Pool & Private Spa, vacation rental in Oia
Swinging Sunset Villa - Private Pool & Private Spa, vacation rental in Oia

Swinging Sunset Villa - Private Pool & Private Spa

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wineryhouse and 2 guest houses, vacation rental in Oia
Wineryhouse and 2 guest houses, vacation rental in Oia
Wineryhouse and 2 guest houses, vacation rental in Oia

Wineryhouse and 2 guest houses

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Armeni Beach House - with private boat service!, vacation rental in Oia
Armeni Beach House - with private boat service!, vacation rental in Oia
Armeni Beach House - with private boat service!, vacation rental in Oia

Armeni Beach House - with private boat service!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Hector Cave House Oia Santorini, vacation rental in Oia
Hector Cave House Oia Santorini, vacation rental in Oia
Hector Cave House Oia Santorini, vacation rental in Oia

Hector Cave House Oia Santorini

Rental Home
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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'The Annouso' villa in Oia, vacation rental in Oia
'The Annouso' villa in Oia, vacation rental in Oia
'The Annouso' villa in Oia, vacation rental in Oia

'The Annouso' villa in Oia

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Seafront Suite With Private Plunge Pool, vacation rental in Oia
Seafront Suite With Private Plunge Pool, vacation rental in Oia
Seafront Suite With Private Plunge Pool, vacation rental in Oia

Seafront Suite With Private Plunge Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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270 Oia's View House I, private swimming pool, sunset view, vacation rental in Oia
270 Oia's View House I, private swimming pool, sunset view, vacation rental in Oia
270 Oia's View House I, private swimming pool, sunset view, vacation rental in Oia

270 Oia's View House I, private swimming pool, sunset view

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Villa 'EMERALD'- Swimming Pool & Private outdoor heated Jacuzzi, vacation rental in Oia
Villa 'EMERALD'- Swimming Pool & Private outdoor heated Jacuzzi, vacation rental in Oia
Villa 'EMERALD'- Swimming Pool & Private outdoor heated Jacuzzi, vacation rental in Oia

Villa 'EMERALD'- Swimming Pool & Private outdoor heated Jacuzzi

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunny Winehouse, vacation rental in Oia
Sunny Winehouse, vacation rental in Oia
Sunny Winehouse, vacation rental in Oia

Sunny Winehouse

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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