Oia, Greece Vacation Rentals

Explore 182 vacation rentals, homes, and villas in Oia for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with hot tub and Homes with Pools, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $187 per night and featuring up to 8 bedrooms and 8 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

182 Vacation Rentals in Oia

Villa Pasion

Ia, South Aegean, GR
1 Bedrooms 2 Guests
Aug 23 - 25
$816 night

The two recently refurbished villas offer guests a sense of renewal in an authentic and elegant environment, without losing their traditional identity or any of the gloriousness of Santorini’s nautical times. Luxury and comfort characterize these neoclassical beauties, that will offer you everything you need to enjoy every moment of your holiday in Santorini. Indulge in absolute relaxation by enjoying the breathtaking view of the caldera from your terrace, as well as the uniquely enchanting sunset that Oia is known for. The one-bedroom villa impresses with its elegant decoration and luxurious sophistication, while its spacious rooms will make you feel like you have arrived at your island home! Across its 50 m², it features one bedroom with a double bed, a living room with built-in sofa and bed, a kitchenette plus a dining area and a bathroom with a shower. It also boasts a private terrace with a hot tub, that enjoys sensational sea and caldera views for guests’ total repose. It has two entrances for more flexibility and can accommodate up to 3 people. Cosmopolitan and scenic, Oia is undoubtedly the place to be in Santorini. Its famous volcanic beauty and the perpetual charm that has been attracting visitors for years, rank the Cycladic island at the top of the list of the world’s most popular travel destinations. The special architecture of the colourful houses, that look like they have been eclectically placed on the summit of a beautiful cliff, create a settlement of rare beauty, with a traditional yet sophisticated aura and dreamlike visuals at every cobblestone path you explore, every corner you turn. Built on the northernmost end of Santorini, it is without a doubt the island’s most popular and picturesque location offering the visitor the most idyllic sunset in the world in addition to spectacular views of the volcano caldera. Wandering along the cobbled alleys, next to the beautiful cave-like houses and neoclassical mansions will fill you with a sense of awe and offer you precious moments of escape from the bustling, everyday life. License number: 1167Κ91001364601 License: 1167K91001364601

Magnificent Santorini Villa | 3 Bedrooms | Villa Royal | Beautiful Caldera View

Oia, South Aegean, GR
3 Bedrooms 7 Guests
Aug 23 - 25
$1,919 night

Villa Royal is a prestigious sanctuary nestled on the mesmerizing island of Santorini. This remarkable estate, originally a captain’s house dating back to the 19th century, stands as a testament to the island’s rich history and enduring allure. Comprising two separate villas ingeniously combined into one, Villa Royal offers an unparalleled setting for family or group holidays, promising an unforgettable escape characterized by unrivaled comfort and sophistication. Step inside and immerse yourself in a world of timeless elegance, where every corner exudes a sense of grandeur and prestige. The interiors, spanning 100 square meters of opulent living space, are meticulously designed to marry tradition with modern-day comforts and aesthetics. Discover two sumptuous bedrooms adorned with plush double beds, ensuring restful nights of slumber, while an additional double bed offers ample accommodation for larger groups. A spacious living room, replete with a dining area and cozy sofa, provides the perfect setting for relaxation and socialization. Indulge your culinary desires in not one, but two fully equipped kitchenettes, where you can whip up delectable meals using the finest local ingredients. Refresh and rejuvenate in two private bathrooms, each boasting a luxurious shower and stocked with lavish bath amenities, bathrobes, and slippers for your comfort. Step outside onto your private terrace, where the magic of Santorini unfolds before your eyes. Two inviting hot tubs beckon, inviting you to immerse yourself in pure bliss as you soak up the breathtaking vistas of the Aegean Sea stretching endlessly before you. From sunrise to sunset, indulge in sublime moments of relaxation and serenity amidst the island’s stunning natural beauty. With the capacity to comfortably accommodate up to 7 guests, Villa Royal offers the perfect blend of space, comfort, and privacy for an unforgettable holiday experience. Each villa boasts its own entrance, ensuring privacy and convenience for guests, while still allowing for seamless interaction and connection among friends and family. Please note: To maintain the exclusivity and privacy of Villa Royal, guests are kindly requested to book the Three Bedroom Villa in its entirety, as it comprises One Bedroom and One Bedroom Villas. This ensures an uninterrupted and luxurious stay, allowing you to fully immerse yourself in the splendor of Santorini. From the captivating views to the lavish amenities, Villa Royal invites you to embark on a journey of unparalleled luxury and indulgence, where every moment is infused with opulence and grace. License: 1243633

Luxury Retreat in Oia | Lathouri Cave Villa | Private Plunge Pool

Oia, South Aegean, GR
2 Bedrooms 4 Guests
Aug 26 - 28
$787 night

Perched above the mesmerizing Aegean Sea, nestled amidst the iconic village of Oia in Santorini, the exquisite Lathouri Cave Villa is a haven of opulence, tranquility, and seclusion. A place where comfort meets serenity, it offers the ultimate retreat for those seeking a truly unforgettable experience. Gaze in awe at the breathtaking Caldera view from your very own private plunge pool, a heated oasis with soothing hydro-massage jets available from April through October. As you unwind on the furnished veranda, you’ll be captivated by the endless vistas of the azure sea, allowing you to bask in the unmatched beauty of this world-renowned destination. Inside, Lathouri Cave Villa boasts ample space, featuring two elegantly designed bedrooms - one with a lavish king-size double bed and the other with two separate single beds. Two luxurious bathrooms await, one equipped with a modern rainfall shower and the other with a relaxing bathtub, ensuring your utmost comfort. The cozy and contemporary living room welcomes you with plush sofas and opens up to the veranda, seamlessly blending indoor and outdoor living. In this idyllic setting, you can indulge in leisurely moments, taking in the magical surroundings while savoring the delights of Santorini. To elevate your stay to new heights, our exclusive concierge services are at your disposal. Our friendly and attentive staff will cater to your every need, making your stay truly exceptional. We offer a range of services, including concierge and travel assistance, yacht and helicopter services, daily maid service, laundry service, breakfast room service, massage treatments, and a warm welcome with refreshing drinks. The amenities at Lathouri Cave Villa are designed to enhance your comfort and leisure. The veranda is thoughtfully furnished with sunbeds and a sunshade, allowing you to relax and unwind under the Mediterranean sun. Inside, you’ll find cable TV, ensuring entertainment during your downtime, as well as complimentary WiFi to stay connected. Should you wish to explore the wonders of Santorini further, our concierge services can arrange private Caldera sailing cruises, traditional boat trips along the coast, guided island tours, scuba diving adventures, horse riding excursions, and bike or car rentals. For connoisseurs, wine tasting experiences can also be arranged to discover the local flavors of this enchanting island. Welcome to Lathouri Cave Villa, where luxury and tranquility merge to create an extraordinary retreat, promising an unforgettable stay in the heart of Santorini’s beauty. License: 1101752

Splendid Santorini Suite | Junior Suite | Caldera Sea Views

Oia, South Aegean, GR
1 Bedrooms 3 Guests
Aug 22 - 24
$1,193 night

Indulge in the contemporary elegance of our Junior Suite, where modern design meets spacious comfort. Ascend to the cozy second-storey loft, featuring a queen-size bed for a restful night’s sleep, complemented by a convenient sofa bed in the living room below. The bathroom invites relaxation with its invigorating massage shower, while the lower level of the suite beckons with a welcoming living area. Step outside to your private patio, where breathtaking panoramic views of the caldera await, accompanied by an inviting outdoor hot tub. Upon arrival, a bottle of local wine sets the tone for your stay, inviting you to unwind in style as you soak in the elegant hot tub under the Mediterranean sky. Elevating your experience further, a host of inclusive amenities and services cater to your every need. Enjoy our Guaranteed Best Available Rate and stay connected with complimentary Wi-Fi throughout your stay. Our attentive concierge team is on hand to provide personalized assistance, ensuring a seamless and memorable visit. Awaken to indulgent mornings with a sumptuous A La Carte Breakfast, setting the stage for a day of exploration and relaxation. Luxuriate in the finest bath amenities by Molton Brown, and revel in VIP perks within the suite, including premium Simmons mattresses and an individual Nespresso machine with daily complimentary capsules. Please note, in our dedication to safety and tranquility, our ambiance is tailored for adults, and we do not accommodate children under the age of 13. For guests traveling with younger companions, alternative arrangements must be made, with the full reservation cost remaining non-refundable. Discover the timeless allure of Santorini at our boutique hotel nestled in the heart of Oia. Each cave house and villa, recognized as "traditionally" built by the Greek National Tourism Organization (GNTO), seamlessly combines old-world charm with modern sophistication, promising an enchanting retreat for discerning travelers seeking unrivaled vistas and unparalleled hospitality. License: 1246621

Villa Magique

Ia, South Aegean, GR
1 Bedrooms 2 Guests
Aug 24 - 27
$509 night

The villa features a comfy queen size bed, air conditioning, a fully equipped kitchenette, with table and chairs, mini fridge, and espresso maker, a beautiful bathroom with shower, complimentary toiletries, slippers, bath and beach towels, a sitting area, flat screen satellite TV, free Wi-Fi access, fiber optic lighting, and an indoor ultra-cool deep plunge pool. The villa is conveniently located in the entrance of Oia, close to the pedestrian street with all the restaurants, galleries, and shops. The traditional settlement of Oia is world famous for its legendary sunsets and lively cultural scene. It is located on the westernmost point of Santorini, and its charming cube-like houses with the colorful façades are perched on the edge of the cliffs, about 150 meters above sea level. Oia is much more quiet than Fira –the island’s capital, located 11 kilometers away-, and its pedestrian narrow winding streets are filled with high-end galleries, boutiques, shops, restaurants, cafés and bars. As dusk falls, hundreds of excitable tourists are looking for the best spot near the ruins of the Venetian castle to watch the sun dipping in the Aegean. It’s when the sky and the sea look redder and redder as the sun gets closer to the horizon, creating a postcard worthy scenery. The charred islets of Palaia and Nea Kameni sizzle in the gleaming sea, and the view after sunset is just surreal. Enjoying dinner in one of the numerous Caldera view restaurants is a memorable experience, not only because of the inconceivable natural beauty of the landscape, but also due to the exquisite local gastronomy and wines. Ammoudi is Oia’s small port. It shelters a handful of fishing boats that provide the catch of the day to the local taverns, and can be accessed by a set of 300 zigzagging steps. The white washed blue-domed churches, the traditional cave houses, the mazy narrow passageways, and mind-blowing sunsets make Oia a fairytale place, trapped in a space and time out of this world. License: 003928001000

Oia Ocean Breeze Villa With Sea & Caldera View

Oia, South Aegean, GR
2 Bedrooms 4 Guests
Aug 22 - 24
$521 night

An architectural gem, this astonishing 60 square meter Villa can accommodate up to 4 persons in its two-bedroom, one bathroom premises. It has its own terrace with outdoor furniture and side views to the sea. It also has access to the shared swimming pool area with sunbeds & umbrellas, enjoying breathtaking views of the Caldera & the Aegean Sea. It is ideal for families & group of friends with its two bedroom and two living room areas. The first bedroom is equipped with a double bed. The second bedroom features a king size bed. There is autonomous air conditioning, a flat-screen satellite TV, complimentary Wi-Fi access, a beautiful bathroom with a shower and complimentary toiletries, slippers, bath and beach towels, as well as a mini fridge, and espresso maker. The villa is located near the church of Agios Georgios in Oia, with easy access to shops, galleries, supermarkets, restaurants, and cafe’s. Indulge in the surreal view of the sea sparkling under the glorious Mediterranean sun, the lunar rocks dropping sheer to the sea-filled crater, the cruise ships peacefully floating in the cobalt blue waters, the dazzling white cube-like houses daringly perched on the edge of the steep cliffs, and the dormant volcano standing as a silent sentinel, guarding the secret of the lost Atlantis. Words are not enough to describe the divine natural beauty of Aegean black diamond. Santorini -repeatedly voted as the most beautiful island in the world by travelers and travel experts- is certainly the jewel in the crown of all Greek islands, with its unearthly raw power, alluring energy, and dramatic landscape. The Villas are seductively nestled on the cliffs of Oia Santorini, where the awe-inspiring sunset dazzles the eye of the beholder with its unreal fiery mix of red, blue, yellow, and orange hues and the infinity of the azure water stretching to the horizon. The villas promise a once-in-a-lifetime vacation experience, with their breathtaking views of Caldera, the volcano and the Aegean, their stunning architecture, immaculate aesthetics, and unsurpassed comfort, style and amenities. Each villa has a unique layout being carved in the volcanic rocks-, indoor and outdoor Jacuzzis and plunge pools, magically hidden fiber optic lighting, ultra-romantic ambiance, a wealth of amenities, and sensational vistas. If you are seeking for villa accommodation in Oia Santorini, look no further than the stunning Villas; where ultimate privacy, luxury and style redefine island chic. License: 1895K12AB34567C9

Villa Doritha, Divine Sea Views, Furnished Terrace, Oia

Santorini, South Aegean, GR
2 Bedrooms 5 Guests
Aug 29 - 31
$464 night

Villa Doritha is a beautifully preserved cave residence that exemplifies the iconic architecture of Oia, suspended along the dramatic caldera cliffs and offering uninterrupted views towards the volcano and the endless blue of the Aegean Sea. Carved into the rock and spanning approximately 55 square metres, this unique retreat blends traditional Cycladic character with modern comforts, creating an atmospheric and memorable setting for a Santorini stay. The interior is thoughtfully arranged with an open-plan kitchen and living area, fully equipped for everyday living, including an oven, stovetop, microwave, refrigerator, coffee machine, toaster, kettle, kitchenware and washing machine. The master bedroom features a queen-size bed and a private en-suite bathroom, while the second bedroom offers three built-in single beds, also with its own en-suite bathroom and direct caldera views, making the villa well suited for families or small groups. Both bathrooms are fitted with walk-in showers, complimentary toiletries, hairdryers, towels and linens. The villa is fully air-conditioned and heated, non-smoking throughout, and provides free Wi-Fi in all areas, a flat-screen TV with satellite and streaming services, and a private entrance for added privacy. Outdoors, a private patio invites guests to relax while taking in the striking sea views, whether enjoying morning coffee or watching the sunset colours sweep across the caldera. Although there is no on-site parking, the central cliffside location places guests within easy reach of Oia’s renowned paths, viewpoints and dining spots. Daily housekeeping is included, and concierge services are available to assist with local arrangements and recommendations. Airport shuttle and additional shuttle services can be arranged upon request at an extra charge, as can a range of wellness treatments such as full-body or couples’ massages. Hiking and other activities are available nearby, independently operated and off-site. Please note that a security deposit may be required prior to arrival, with full details confirmed before check-in. Any optional services, including transfers and massages, are payable locally unless otherwise agreed in advance. Villa Doritha offers an authentic caldera living experience, combining privacy, comfort and one of Santorini’s most captivating settings. License: 1057647

Oia Secret Escape Villa with Private Pool with Sea & Caldera View

Oia, South Aegean, GR
2 Bedrooms 4 Guests
Aug 23 - 25
$844 night

An architectural gem, this astonishing 60 square meters, the two-story villa can accommodate up to 4 persons in its two-bedroom, two-bathroom premises. It enjoys stunning Caldera, volcano and Aegean vistas from its private verandas, and is elegantly decorated with vintage artifacts and furniture. The upper floor features a split-level space, accommodating a separate area with a queen size bed and a desk surface, and a spacious sitting area with couch, table, and chairs, mini-fridge and espresso maker, a flat-screen TV, as well as a bathroom with shower. The lower floor, which is connected to the upper by an indoor staircase, features a second bedroom with a queen size bed, desk surface, a second bathroom and a separate shower with rain showerhead, as well as an indoor jetted spa tub. This villa has two separate private verandas, both located on the lower level and enjoying stunning views of the Aegean and the Volcano. The first is equipped with a table and chairs, and the second with a semi-covered private swimming pool and sunbeds. The villa is located near the church of Agios Georgios in Oia, with easy access to shops, galleries, supermarkets restaurants and cafe’s. Complimentary breakfast is served daily at our cafeteria close to the villa. Indulge in the surreal view of the sea sparkling under the glorious Mediterranean sun, the lunar rocks dropping sheer to the sea-filled crater, the cruise ships peacefully floating in the cobalt blue waters, the dazzling white cube-like houses daringly perched on the edge of the steep cliffs, and the dormant volcano standing as a silent sentinel, guarding the secret of the lost Atlantis. Words are not enough to describe the divine natural beauty of Aegean black diamond. Santorini -repeatedly voted as the most beautiful island in the world by travelers and travel experts- is certainly the jewel in the crown of all Greek islands, with its unearthly raw power, alluring energy, and dramatic landscape. The Villas are seductively nestled on the cliffs of Oia Santorini, where the awe-inspiring sunset dazzles the eye of the beholder with its unreal fiery mix of red, blue, yellow, and orange hues and the infinity of the azure water stretching to the horizon. The villas promise a once-in-a-lifetime vacation experience, with their breathtaking views of Caldera, the volcano and the Aegean, their stunning architecture, immaculate aesthetics, and unsurpassed comfort, style and amenities. Each villa has a unique layout being carved in the volcanic rocks-, indoor and outdoor Jacuzzis and plunge pools, magically hidden fiber optic lighting, ultra-romantic ambiance, a wealth of amenities, and sensational vistas. If you are seeking for villa accommodation in Oia Santorini, look no further than the stunning Villas; where ultimate privacy, luxury and style redefine island chic. License: 1895K12AB34567C9

Villa Pure

Ia, South Aegean, GR
1 Bedrooms 2 Guests
Aug 21 - 24
$811 night

The villa is bright and airy, benefiting from the gorgeous Aegean sun through its numerous windows and balcony doors, has a queen size bed –oriented towards the sea, to take advantage of the view-, a sitting area with a couch and coffee table, a drawer and desk surface, a flat screen satellite TV, free Wi-Fi access, a fully equipped kitchenette, with mini fridge and espresso maker, air conditioning, a separate shower and bathroom, complimentary toiletries, slippers, bath and beach towels. The villa is conveniently located in the entrance of Oia, close to the pedestrian street with all the restaurants, cafés, galleries, and shops. The traditional settlement of Oia is world famous for its legendary sunsets and lively cultural scene. It is located on the westernmost point of Santorini, and its charming cube-like houses with the colorful façades are perched on the edge of the cliffs, about 150 meters above sea level. Oia is much more quiet than Fira –the island’s capital, located 11 kilometers away-, and its pedestrian narrow winding streets are filled with high-end galleries, boutiques, shops, restaurants, cafés and bars. As dusk falls, hundreds of excitable tourists are looking for the best spot near the ruins of the Venetian castle to watch the sun dipping in the Aegean. It’s when the sky and the sea look redder and redder as the sun gets closer to the horizon, creating a postcard worthy scenery. The charred islets of Palaia and Nea Kameni sizzle in the gleaming sea, and the view after sunset is just surreal. Enjoying dinner in one of the numerous Caldera view restaurants is a memorable experience, not only because of the inconceivable natural beauty of the landscape, but also due to the exquisite local gastronomy and wines. Ammoudi is Oia’s small port. It shelters a handful of fishing boats that provide the catch of the day to the local taverns, and can be accessed by a set of 300 zigzagging steps. The white washed blue-domed churches, the traditional cave houses, the mazy narrow passageways, and mind-blowing sunsets make Oia a fairytale place, trapped in a space and time out of this world. License: 003928001000

Stunning Oia Villa with Stunning Sea and Caldera views | Private Pool | Air Conditioning | Infinity Heated Pool

Oia, South Aegean, GR
3 Bedrooms 4 Guests
Aug 24 - 26
$1,641 night

Villa Ioulia harmoniously combines classic Cycladic architectural elements with modern comforts, making it an ideal retreat for couples, families with adult children, or groups of friends. This exquisite villa boasts two double bedrooms, a charming loft with two single beds, two well-appointed bathrooms, and a private infinity pool, all set against the backdrop of breathtaking vistas overlooking the Caldera and the Aegean Sea. Step into an oasis of tranquility within this villa, adorned with a soothing color palette of off-white and earthy tones, enhanced by soft fabrics and dark wood furnishings. The villa also features a spacious lounge area that adds to your overall comfort. The elegant interior design creates a welcoming and homey atmosphere. Take in the serene surroundings from your private balcony or enjoy the generous living space indoors, where you’ll find state-of-the-art technology and an array of thoughtful extras to cater to your needs. Each luxury villa is thoughtfully equipped with contemporary amenities, including an outdoor hot tub, plush towels, comfortable slippers, a luxurious bathrobe, a hairdryer, premium bath amenities, a coffee machine, a well-stocked mini-bar, a secure safe deposit box, a smart TV, high-speed WiFi, key card access, individual air conditioning control, a cozy seating area, a terrace, outdoor furniture, sun loungers, and a sun umbrella. Every villa provides breathtaking views over the Caldera and the majestic Volcano. Notably, the loft bedroom exudes a whimsical charm and is more suitable for older children. This bedroom is also only available on request. Please note that air-conditioning is available in all rooms apart from the loft bedroom. In addition to the breathtaking views and luxurious amenities, Villa Ioulia offers a range of conveniences, including air conditioning, alarm clock, bath amenities, bathrobes, slippers, a bathroom with a shower, a closet, coffee facilities, daily maid service, a dining table, electronic locks, a flat-screen TV, hairdryer, individually controlled air conditioning, an indoor jacuzzi, interactive TV, internet access, a living room, a marble bathroom, a mini-bar, non-smoking room options, a private balcony, a private terrace, a razor plug, refrigerator, safe deposit box, sea views, a sitting area, soundproof windows, television, turn-down service, veranda, wake-up call service, a welcome drink, and complimentary Wi-Fi internet access.

Villa Orisontas

Ia, South Aegean, GR
3 Bedrooms 6 Guests
Aug 31 - Sep 2
$1,638 night

Villa Orisontas is part of a residential complex, in the Perivolas area of Oia, with private entrance from the main street. The distance between the villas is only 60m which makes them the perfect retreat for parties of friends or family and for social events especially for weddings. It can be rented independently or together with one or more of the villas Windmill, Cave, Castro and Sentiment. The colour and design have been carefully blended with Aegean traditional touches to reward the guests with a perfectly romantic ambiance. The Orisontas Villa with a surface of 65 m2 is suitable for 6 guests and is designed based on an open space plan. The villa features an interconnecting bedroom, that is a no doors plan. The villa features 2 Bedrooms with King Size bed, 1 Bedroom with French bed (140cm wide) and a Living room with 1 Sofa bed. Gieusts are served by two bathrooms and a fully equipped kitchen. The outside area has a Terrace with a big Outdoor Heated Jacuzzi with magnificent Caldera View, table & chairs. Facilities include, Wi-Fi in all areas inside and outside, smart TV with Wi-Fi connection, air conditioning, LCD TV, CONNEX TV programs, safe box, luxurious bathroom amenities, Hairdryer, Slippers & bathrobes and coffee machines. Built on Oia’s most famous cliffs, offering dazzling views towards the volcano and the whole of the island, it is a villa that stands out in its simplicity. It is situated in the Perivolas area of Oia, with a private entrance from the main street. Exuberant through its minimalistic nature, traditional yet elegant contemporary, it offers the comforts of a modern and functional house.  Santorini, with its rugged Aegean beauty, is the most southern island of the Cyclades.  It is famed for its sunsets, wine and the turquoise sea that surrounds it.  From its dramatic birth in the apocalyptic volcanic explosion of 1450 BC to the modern sugar cube villas hugging its sheer cliffs, Santorini (also known as Thira) is indisputably the most dramatic and breathtaking of all the Greek island License: 1167K91000966601

Vacation Rentals in Oia by Amenities & Features

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Vacation Rentals Near Oia

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