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Villa vacation rentals in Oia

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Top-rated villa rentals in Oia

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Top guest favorite

A charming courtyard is displayed, featuring comfortable outdoor seating arrangements and a tranquil infinity pool in the background. The villa's exterior is constructed with local stone, illuminated softly by outdoor lighting, while the sky captures a gradient of blues and wispy clouds as twilight approaches.

Villa in Santorini

4.98 out of 5 average rating, 121 reviews

SPECTACULAR SANTORINI VILLA-CAR RENTAL INCLUDED

Description: Mansion Kyani is a secluded Hillside villa in Santorini's prettiest village. It offers three self-contained apartments spread over two spacious floors, a sunny terrace providing great views, and a huge yard with private pool & copious lounging spots. -A manual 5seater Car Rental (Fiat Panda or similar) is offered complimentary for the duration of your stay. This does NOT apply for special offers and not guaranteed for last minute reservations (depends upon agent's availability).

Top guest favorite

A private terrace features a spacious infinity pool alongside a separate heated plunge pool. Comfortable lounge chairs are positioned by the pool, and a shaded dining area is visible under a modern pergola. Clear views of the sea and distant landscapes are offered.

Villa in Pyrgos Kallistis

4.99 out of 5 average rating, 114 reviews

Santorini Sky | Panoramic Villa *NEW*

SPECIAL 2025 RATES. BOOK NOW! As seen in Vanity Fair, Conde Nast Traveller and Architectural Digest, this amazing villa will take your breath away. With panoramic windows in every room, a large private terrace with infinity pool, and a separate heated jacuzzi, you can enjoy incredible sea views from sunrise to spectacular sunset. This is paradise! Includes complimentary access to our Sky Lounge, with breakfast pantry items and snacks throughout the day. Contact us today with any questions!

A private heated jacuzzi is nestled on a terrace, overlooking a tranquil sea and vibrant sunset. The horizon is painted in warm hues as the sun descends, while the sleek white structure provides a contrasting backdrop.

Villa in Pyrgos Kallistis

4.97 out of 5 average rating, 111 reviews

Martynou View Villas

Martynou View villas is a private property,located in Santorini Pyrgos village. Just a few steps away from restaurants cafe and more shops.Only 10 minutes driving distance from central Fira and from the best beaches of the island. This is an ideal choice for couples. The property offers a spacious living room with kitchen, bathroom,double bed,air condition,coffee machine,TV,fridge,Wi-fi, soundtrack,private parking and a lovely balcony with private heated jacuzzi and stunning sea view!

An outdoor terrace is shown, featuring a dining table surrounded by light-colored chairs. A private jacuzzi is visible on one side, with panoramic views of the sunset over the sea and distant hills. The space is complemented by sheer drapes and a warm glow from the setting sun.

Villa in Firostefani

4.85 out of 5 average rating, 128 reviews

Sunset View Villa Santorini - Outdoor Jacuzzi

Exclusive Luxury Villa with breath-taking PANORAMIC views of the sea, Caldera & Sunset. Upstairs - One of the largest private jacuzzi terraces in Santorini with pergola & kitchen/bar, stunning views and Alfresco dining and lounging. Downstairs - 3 double Bedrooms, 2 bathrooms, lounge/dining room, Modern kitchen, outdoor dining table in the tranquil courtyard. Laundry with washer and drier. Daily clean, linen, towels & toiletries. Personal Manager & concierge services.

A private terrace features wooden lounge chairs surrounding a hot tub, offering expansive views of the Aegean Sea and the volcanic islands at sunset. The tranquil atmosphere is enhanced by soft, pastel skies reflecting over the water.

4.98 out of 5 average rating, 139 reviews

Calderas Hug 1 (Panoramic Sea View& Prive Hot Tub)

Calderas Hug 1 is a suite perfectly situated in the famous Caldera, offering an astonishing direct sea view to the infinity azure of the Aegean sea! Our property, is beautifully settled in the volcanic surface of Caldera cliff, following the traditional Cycladic white-washed architectural principals, providing our Guests a sense of serenity and a plethora of luxury amenities.

A serene outdoor area features a private pool with a smooth edge overlooking the sea. Comfortable sun loungers are positioned nearby, with captivating views of the sunset reflecting on the horizon and the gentle slopes of Santorini in the background.

4.73 out of 5 average rating, 107 reviews

180° Caldera by Stylish Stays

“180° Caldera” is located at the renowned Firostefani area of Santorini and has a panoramic, 180° view of the sought after volcanic caldera of the island. The Villa is built in the traditional local style with the iconic amphitheatric Santorinian fashion, which gives the impression of a balcony hanging over the Caldera and the Aegean Sea.

A private pool is featured within a sunlit terrace, surrounded by modern architectural elements. The clear water of the pool reflects the sky, while lounge chairs are positioned nearby for relaxation. The expansive space allows for unobstructed views of the surroundings.

Villa in Akrotiri

4.95 out of 5 average rating, 120 reviews

Serra Exclusive Suites

Our newly-built suites are providing a modern and luxury setting with the best view of the entire Caldera of Santorini (the cliffs, the volcano, Oia, Fira, etc.) where our guests will be pampered and feel like home thanks to the famous Greek hospitality. You can explore an unparalleled travel experience you would not miss for the world.

Top guest favorite

Two wooden lounge chairs are positioned on a concrete terrace, offering unobstructed views of the caldera. Two lanterns with flickering candles provide ambient lighting as the sun sets over the water, creating a serene space for relaxation.

5 out of 5 average rating, 142 reviews

Loukia House

Loukia House is a traditional Cycladic cave house carved inside the Oia cliff. The beautiful arched ceilings stretch along the indoor and outdoor space. Its unique location offers panoramic views of the whole island and the caldera. A relaxing terrace gives a sense of privacy in the most sought-after spot in Santorini.

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Stylish accommodations and amenities

Popular amenities for Oia villa rentals

Free parking on premises

Air conditioning

Private villa rentals

A tranquil pool area features a cozy love-seat with soft cushions, facing a stunning view of the coast at sunset. Lush greenery frames the scene, while a shaded terrace offers a comfortable spot for relaxation. The inviting pool reflects the sky's warm colors.

Villa in Santorini

5 out of 5 average rating, 21 reviews

Eolia Senior Villa

An open-plan living area is presented, featuring a modern kitchen with sleek cabinetry and a cozy seating arrangement. Large windows offer a view of the ocean, while light-colored walls and wooden accents create a bright and airy atmosphere.

Villa in Imerovigli

4.91 out of 5 average rating, 23 reviews

Deluxe Villa with Private Pool

Top guest favorite

A private pool is featured, surrounded by smooth stonework, offering expansive views of the ocean. A sun hat and sunglasses rest on a rolled towel, adding to the serene atmosphere. The horizon showcases distant landforms and a clear blue sky.

5 out of 5 average rating, 22 reviews

103. Lavanda | Superior 2-Bedroom Villa, Jacuzzi

Top guest favorite

The living area features curved white walls and two built-in seating areas adorned with grey cushions. A low coffee table sits centrally on a light brown rug, with natural light illuminating the space through arched windows that lead to a visible bathroom.

5 out of 5 average rating, 44 reviews

Inspire Santorini Luxury Villas - A2

A private terrace features a jacuzzi surrounded by natural stone walls and sunlight streaming through a slatted roof. Lush greenery peeks from above, creating a serene outdoor setting, while steps lead to an entrance shaded by the structure.

Villa in Monolithos

4.98 out of 5 average rating, 61 reviews

Blue Diamond Suite with Hot Tub *Aegean Diamonds*

A modern pool area is set against a stunning backdrop of mountains and the sea. The clear water glistens in the sunlight, surrounded by white lounge chairs and elegantly arranged potted plants, contributing to the serene atmosphere.

Villa in Pyrgos Kallistis

4.94 out of 5 average rating, 63 reviews

Brand new villa with swimming pool

A serene outdoor area features comfortable lounge chairs placed on a textured surface. Soft lighting illuminates a rustic dining space under a wooden pergola, enhancing the tranquil setting. A plunge pool is visible, along with the natural landscape of cliffs in the background.

Villa in Emporio

4.96 out of 5 average rating, 49 reviews

Canava Villas Winery Estate -Santorini

A private outdoor area features a pool with clear water, surrounded by a patio fitted with lounge seating. An arched entryway leads into the villa interior. Two wooden chairs and a small table are positioned near the entrance, enhancing the inviting outdoor space.

Villa in Mesaria

4.89 out of 5 average rating, 9 reviews

Living Moments Villa Amersa

Luxury villa rentals

The villa is shown at twilight, revealing its elegant architecture. A private pool reflects the evening sky, with lounge chairs positioned beside it. Soft lighting highlights the outdoor spaces, and palm plants frame the entrance, creating a welcoming ambiance.

Villa in Mesaria

4.92 out of 5 average rating, 25 reviews

Aleria Santorini Villa

Top guest favorite

A modern villa features a private pool surrounded by sun loungers and lush landscaping. The outdoor area includes a shaded seating space under a pergola, with warm lighting illuminating the pathway. The tranquil ambiance is enhanced by the evening sky.

Villa in Megalochori

4.96 out of 5 average rating, 25 reviews

Philosophia Luxury Villa

An outdoor area featuring a private pool surrounded by natural stone, a wooden dining table with several chairs, and a shaded lounge with thatched roofs. Lush greenery provides privacy, while a sun shower adds convenience for pool guests. The space offers a serene ambiance for relaxation.

Villa in Emporio

4.9 out of 5 average rating, 51 reviews

Rock Villas Complex| Castle View | Pool & Hot Tub

The exterior view of the villa at dusk features soft blue lighting illuminating the white facade. A private swimming pool is visible, surrounded by a stone border. Spacious terraces and outdoor seating areas are included, creating a welcoming ambiance for relaxation.

Villa in Megalochori

4.95 out of 5 average rating, 43 reviews

Alchemy Villa - 3 Bedrooms, 3 Baths & Prive Pool

An outdoor relaxation area features two spacious lounge chairs positioned beside a shimmering swimming pool. The stone wall of the villa contrasts with the soft glow from interior lights. Large glass doors offer a glimpse into the modern interior, emphasizing the blending of indoor and outdoor spaces.

5 out of 5 average rating, 15 reviews

Villa Trace-2 BR/Heated private pool, Sea view

An open-air terrace showcases outdoor seating arrangements and a hot tub, with panoramic views of the sea at sunset. The light-colored surfaces reflect the soft hues of the sky, while greenery adds a touch of nature to the space.

4.94 out of 5 average rating, 67 reviews

3 bed villa, @ Fira center Sea view,outdoor hottub

A private balcony offers a stunning view of the Aegean Sea at dusk, showcasing soft blue and orange hues in the sky. A jacuzzi is positioned nearby, and a small table with two chairs is illuminated by a warm light, creating a cozy setting.

5 out of 5 average rating, 5 reviews

Pure Bliss Villa, caldera view & jacuzzi

Two lounge chairs are positioned beside a private infinity pool, offering an unobstructed view of the ocean at sunset. The sky transitions in soft shades of orange and pink, while the tranquil waters reflect the warm hues. Lush greenery is present nearby.

4.98 out of 5 average rating, 42 reviews

Saint Apostles 3-bedroom villa with private pool

Villa rentals with a pool

An outdoor area features an inviting private pool surrounded by several loungers. The landscape includes a clear view of the Aegean Sea in the background, framed by a bright blue sky. Light-colored stone walls and minimal landscaping contribute to a serene environment.

Villa in Exo Gialos Karteradou

4.92 out of 5 average rating, 73 reviews

VILLA WAVES 2 SANTORINI

Villa in Vothonas

5 out of 5 average rating, 31 reviews

Santo Bloom "giio" Deluxe Villa with Private Pool

An evening view of a private terrace showcases a sleek pool with illuminated water in a calming blue hue. Comfortable seating is arranged nearby, and a small dining area is positioned in the background. The sky transitions into deep hues as twilight sets in.

4.98 out of 5 average rating, 57 reviews

Filoxenia Luxury Villa-2 Bedroom with private pool

A serene swimming pool is captured from above, featuring clear blue water. A person is swimming gracefully, while lounge chairs are positioned nearby, accompanied by a small table with refreshments, enhancing the tranquil environment.

Villa in Vothonas

4.95 out of 5 average rating, 37 reviews

Romantic Villa With Sea View Car Included

A clear swimming pool is surrounded by palm trees and lounge chairs, offering a relaxing outdoor space. The white villa in the background is complemented by blooming plants and a mountainous landscape under a bright blue sky.

Villa in Kamari

4.83 out of 5 average rating, 156 reviews

Studio Santorini Twin/Double

An outdoor lounge area features dark-colored seating alongside a sparkling pool. Sunbeds are arranged beside the pool, accompanied by a shaded area provided by a large umbrella. A table displays a selection of fresh fruits and drinks, with the ocean visible in the background.

Villa in Exo Gialos Karteradou

4.98 out of 5 average rating, 64 reviews

Villa Concha Con Perla Santorini

Top guest favorite

An outdoor area is showcased, featuring a private pool surrounded by green grass. Two lounge chairs are positioned nearby. Nearby, two stylish chairs offer additional seating. The bright white walls of the villa contrast with the blue sky, creating a serene and inviting atmosphere.

Villa in Santorini

5 out of 5 average rating, 59 reviews

Kyklos villas - private heated pool Villa

Villa in Karterádos

5 out of 5 average rating, 23 reviews

George Farm Land villa with private swimming pool

Quick stats about villa rentals in Oia

Total rentals
70 properties
Nightly prices starting at
R3,013 ZAR before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
30 properties have a pool

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