Villa holiday rentals in Oia

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.

4.99 out of 5 average rating, 148 reviews

Spectacular Private Mansion- Car Rental included *

Mansion Kyani is a secluded hillside villa in Santorini's prettiest village. It features three self-contained suites spread over two spacious floors, ensuring distinct private living areas for your group. Enjoy the sunny terrace with panoramic views, an expansive courtyard with a private pool, garden & many lounging spots. -A manual 5seater Car Rental (Cat.C) is included. *This does NOT apply for special offers and not guaranteed for last minute reservations (depends upon agent's availability).

A heated plunge pool is featured within a uniquely shaped archway, with clear blue water reflecting the sun. A stunning view over the ocean and distant islands is visible through the opening. Decorative cushions and a small table with refreshments enhance the inviting atmosphere.

4.99 out of 5 average rating, 175 reviews

Ventus Paradiso Villa, Outdoor Heated Plunge Pool

Our cave villa comes with sentimental value as it belonged to our grandmother. Dated back to 1920's brings a great heritage. The villa was totally renovated in 2015, transforming a traditional cave into a luxury residence following faithfully the unique cycladic architecture with exceptional modern esthetics. The villa consists of two bedrooms with ensuite bathrooms, a dining area and a small kitchenette. It features a heated plunge pool and an upper terrace with panoramic view over Caldera.

4.97 out of 5 average rating, 150 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!

4.91 out of 5 average rating, 173 reviews

A private Jacuzzi tub is positioned on a balcony, with a stunning view of the Aegean Sea and a sunset reflecting on the water. Soft clouds are visible in the sky, and a rolled towel is neatly placed beside the tub.

Villa in Vourvoulos

Levantis Suite - Private Hot Tub & Sea View

Levantis Suite (57 sq.m.) at La Estrella Luxury Suites embodies refined Cycladic elegance, perched in serene Vourvoulos just 600 m from Imerovigli. Offering uninterrupted Aegean Sea views, it features a heated private jacuzzi on the balcony, exquisite décor, premium amenities, daily housekeeping, and private parking. Ideally located near a mini market (400 m) and charming local tavernas (350 m), the suite is only 1.3 km from the Caldera, set in a peaceful and quiet area of Santorini.

4.96 out of 5 average rating, 198 reviews

A serene outdoor space features a small pool illuminated in soft blue, surrounded by white cave-style walls. A comfortable seating area with cushions is visible, alongside a decorative lantern casting a warm glow, creating an inviting atmosphere for relaxation.

Villa in Karterados

MyBoZer Cave Villa

MyBozer Cave Villa is a traditional cave style house located in traditional village of Karterados. This cave style luxury villa offers high end amenities and facilities in indoor area and outdoor area . Near the villa only 5 minutes by foot you can find the local bus stop ,also near by you can find everything you need like restaurants,super market,coffee shops ,patisserie,the police station and the general hospital of Santorini.

4.97 out of 5 average rating, 203 reviews

Luxury Villa | Outdoor Hot Tub | Sea & Sunset View

Vista d’Oro Luxury Villa offers a peaceful stay in Oia, just 500 meters from the village’s famous main pathway, around a 10-minute walk through a footpath or a 2-minute drive. Ideally located within walking distance of Ammoudi Bay and Katharos Beach, the villa lets you enjoy the best of Oia while retreating to a quiet setting. From your private terrace, you can take in Santorini’s iconic sunset away from the busy crowds.

An outdoor terrace features two comfortable lounge chairs facing the expansive Aegean Sea. The calm waters reflect clear blue skies, while views of nearby islands enhance the serene atmosphere. A railing provides safety while allowing unobstructed sightlines of the breathtaking scenery.

4.94 out of 5 average rating, 216 reviews

Calderas Hug 2 Suites(Sea View& Prive Hot Tub)

Calderas Hug & Sea View 2 is a villa with two suites perfectly situated in the famous Caldera, offering an astonishing direct sea view to the infinity azure of the Aegean sea! Our properties, are 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.

4.96 out of 5 average rating, 162 reviews

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

Serra | Caldera View Suite, Private Pool & Hot Tub

Perched above the Aegean, our newly built suites offer panoramic views across the entire Santorini Caldera—from the volcanic cliffs to Fira and Oia. Designed for refined Cycladic luxury, Serra combines modern comfort with authentic Greek hospitality. Relax on your terrace, unwind in your private pool, or soak in your heated jacuzzi while enjoying an elevated, unforgettable island stay.

4.98 out of 5 average rating, 228 reviews

A serene outdoor space is highlighted, featuring sun loungers positioned by a swimming pool. The horizon glows with hues of orange and yellow as the sun sets, while a hanging chair gently sways nearby. Natural stone elements frame the view, adding texture to the scene.

Villa in Fira

Saints Apostles Villa with private pool

Saints Apostles is located in a quite area 1,5 klm from Fira town (20 minutes by walking or 2 minutes by car). Is fully luxury furnished , unlimited sea view to the east side of the island (on the beach side) and to the sunrise. The house is divided in 2 villa apartments with each apartment been private with its one swimming pool and all the amenities we describe.

An outdoor seating area features wooden lounge chairs positioned to face the ocean, capturing a sunset view. A dining table is visible in the background. Lanterns are placed on the ground, and trees provide a natural frame against the colorful sky.

4.99 out of 5 average rating, 220 reviews

Villa Aronia

This immaculate, 80 m^2 and fully equipped Villa invites comfort and tranquility. Highlights include breathtaking view, secluded beach, only 20 meters away, spacious garden setting for relaxing and entertaining and private parking. Perfect for anyone, this home is ideally positioned to enjoy all year round in Santorini.

4.94 out of 5 average rating, 163 reviews

Luxury Villa with Hot Tub in the heart of Oia

Villa Rosaviglia is a contemporary and peaceful oasis, perfectly designed to experience the beauty of spectacular Santorini. Ideally located in the very center of Oia Village, it offers easy access with no stairs—allowing for a smooth and comfortable stay just steps from everything.

A private terrace features a shimmering pool with views of the sea and the caldera. Whitewashed buildings in Oia line the cliffside under a clear blue sky, creating a serene backdrop for relaxation.

4.87 out of 5 average rating, 212 reviews

Top Caldera view villa with Hot Tub in Oia

This charming, spacious villa sits at the highest point of the village, offering stunning, unobstructed views of the famous Caldera and the volcano. With a king-size bed and a private balcony featuring a hot tub, it promises unforgettable moments of relaxation and pure enjoyment.

Popular amenities for villa rentals in Oia

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.95 out of 5 average rating, 113 reviews

Villa in Karterados

Villa Makrilis | Spacious Villa for Groups Jacuzzi

4.99 out of 5 average rating, 188 reviews

The villa showcases a private pool in vibrant turquoise, surrounded by comfortable sun loungers and chic seating areas. The whitewashed structure features a covered terrace that offers shade. Lush greenery and decorative accents enhance the tranquil environment.

Villa in Kamari

Santorini Filoxenia Luxury villa

4.88 out of 5 average rating, 143 reviews

A private swimming pool is framed by sun loungers, offering a serene space for relaxation. A stone terrace features a shaded dining area, with stunning views of the sunset over the calm sea, creating a peaceful atmosphere.

Villa in Panagia Kalou

Abelomilos Luxury by The Sea

4.95 out of 5 average rating, 132 reviews

A heated jacuzzi features glowing blue water, framed by a wooden deck. Nearby, an outdoor dining area with a table and chairs is positioned under a shaded pergola. The expansive view includes the tranquil sea and distant hills, illuminated by the evening sky.

Villa in Akrotiri

Premium Two Bedroom Villa with Jacuzzi & Sea View

4.95 out of 5 average rating, 120 reviews

An inviting balcony features a jacuzzi set against the backdrop of a twilight sky. Two glasses of red wine are positioned on the ledge, and lounge seating is arranged nearby. Soft lighting enhances the tranquil ambiance, while panoramic views extend towards the horizon.

Villa in Megalochori

Blanca Luxury Villa

An elegant wrought iron gate is framed by a white wall, leading to a stunning view of the sea and distant islands. Bright blue skies and gentle clouds accompany the scene, enhancing the picturesque setting.

4.92 out of 5 average rating, 101 reviews

Villa DALI Danae with volcano view & large jacuzzi

Two wooden lounge chairs are positioned beside a plunge pool, with a small table holding a wine glass and a bottle of wine. The view overlooks the Aegean Sea and distant volcanic islands, with soft pastel hues accenting the landscape.

4.95 out of 5 average rating, 22 reviews

Little Rock Villa-Oia. Entire Cave House Oia

Two wooden chairs are positioned on a terrace, facing the expansive view of the blue sea and distant cliffs. One chair features red and white stripes, while the other is adorned with blue and white stripes. A clear blue sky complements the serene waters.

4.97 out of 5 average rating, 66 reviews

Villa Calliope

Luxury villa rentals

4.94 out of 5 average rating, 108 reviews

White Orchid Villa | Private Pool | Sunset View

4.94 out of 5 average rating, 201 reviews

A crystal-clear plunge pool glistens under the sun, surrounded by whitewashed stone walls. Decorative planters add splashes of green, while pink flowers provide a soft contrast. The image captures a backdrop of traditional Santorinian architecture against a bright blue sky.

Villa in Fira Santorini

The Painters House

A tranquil outdoor seating area is set against a backdrop of whitewashed buildings and blue domes. The shaded nook features a comfortable bench adorned with striped cushions, offering a serene space for reading or relaxing amid the picturesque Santorini landscape.

4.94 out of 5 average rating, 36 reviews

Aris Cave indoor plunge pool by SV

A tranquil infinity pool nestles against a backdrop of white architecture and vibrant flowers. The pool water reflects the clear blue sky, complemented by a nearby blue-domed church. The scene evokes a serene outdoor space perfect for relaxation.

5.0 out of 5 average rating, 72 reviews

Luxury Villa BLUE DOME, the 5* villa experience

5.0 out of 5 average rating, 9 reviews

Athera Luxury Villas

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.

5.0 out of 5 average rating, 58 reviews

Inspire Santorini Luxury Villas - A2

An outdoor terrace features a private heated plunge pool, surrounded by lounge chairs and a dining area. Natural stone walls accent the covered space, offering a view of the expansive glass doors that lead into the suite's combined living and sleeping area.

4.96 out of 5 average rating, 72 reviews

Santorini Sky | Retreat Suite | #1 in Santorini

Luxe

An outdoor terrace features an infinity pool surrounded by sunbeds with dark towels. A shaded seating area and potted plants enhance the space, while expansive views of the sea and surrounding landscape are visible in the background.

5.0 out of 5 average rating, 20 reviews

Kamini White 2 Bedroom

Villa rentals with a pool

A serene scene features two glasses positioned at the edge of a private pool, reflecting the vibrant hues of a sunset. Silhouettes of trees frame the view, enhancing the tranquil ambiance of the villa.

4.79 out of 5 average rating, 130 reviews

Queen Albus Villa with Private Pool, Sunset View

4.99 out of 5 average rating, 104 reviews

An infinity pool extends from the balcony, offering an unobstructed view of the caldera and surrounding landscape. The horizon showcases a mix of white structures and natural elements, under a partly cloudy sky, creating a serene atmosphere.

Villa in Akrotiri

Stela caldera view cave/private mini pool/jacuzzi

4.88 out of 5 average rating, 98 reviews

An inviting private swimming pool is situated on the terrace, with the tranquil Aegean Sea in the background. The sky is adorned with hues of orange and purple as the sun sets, while surrounding greenery and modern seating areas enhance the serene atmosphere.

Villa in Foinikiá

Astrea Suites: Villa Finikia- Aegean Sea View

4.94 out of 5 average rating, 18 reviews

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

Private Pool Villa, Santorini Village Retreat

5.0 out of 5 average rating, 7 reviews

Villa in Vothonas

Maison Dalidaz Luxury Villa & Pool

A private terrace features a refreshing pool surrounded by wooden loungers. Scenic views of rolling hills and the ocean horizon are visible in the background. The outdoor area includes a shaded seating space for relaxation, all framed by natural stone walls.

5.0 out of 5 average rating, 86 reviews

104. Cactus | Executive 3-Bedroom Villa with Pool

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.

4.94 out of 5 average rating, 77 reviews

Brand new villa with swimming pool