Holiday rentals with breakfast in Oia

A scenic view from HELIOS Cave House shows a guest overlooking the caldera and the sea. Whitewashed buildings line the hillside, accentuated by the brilliant blue sky. The image captures the serene atmosphere that surrounds the property, inviting relaxation and tranquility.

4.92 out of 5 average rating, 192 reviews

SantoriniParadise: HELIOS cave house, sunset view!

HELIOS Cave house is a roomy, well-lit, romantic love nest! In the heart of old Oia, it offers an unobstructed view of Oia's famous sunsets! That is why SISTERHOOD OF THE TRAVELLING PANTS was filmed just there! It features 2 double beds, a sofa bed, a corner sofa & a red stylish bathtub. There is a little, cozy yard and from SANTORINI PARADISE HOUSES' private rooftop you enjoy amazing sunsets & the Ammoudi port. Jacuzzi for 3 persons is available on Tuesday, Thursday & Saturday, just 2 min away

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Cycladic home in Santorini

A spacious rooftop terrace features a heated Jacuzzi surrounded by sunbeds. The stunning view showcases the Caldera and Aegean Sea at sunset, with colorful skies and the scenic cliffs of Fira in the background.

4.99 out of 5 average rating, 144 reviews

Three bedroom Villa with two Caldera View Jacuzzi

This luxury villa has the best location and feature specious terraces with famous view of Caldera and Aegean sea .Roof top terrace have heated Jacuzzi and comfortable sun-lounges.There is outdoor furniture next to Jacuzzi where you can enjoy breakfast and dinner with unforgettable view . Daily breakfast and cleaning make your stay comfortable .Each bedroom have private bathroom . In a walking distance you will find restaurants,bars, museums and supermarkets.Food delivery available.Free wi-fi

ValueLocationHiking

4.99 out of 5 average rating, 173 reviews

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.

Villa in Merovígli

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.

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Guest suite in Pyrgos Kallistis

A private terrace features a tranquil pool surrounded by a smooth, light-colored deck. Cozy, round seating is positioned nearby, offering a view of the expansive blue sea and hills in the distance. A small wooden table holds refreshments, inviting relaxation.

4.96 out of 5 average rating, 202 reviews

Infinity Pool • Luxury Villa • Sea View

Enjoy breathtaking sunsets and panoramic views of the Caldera, volcano and Aegean Sea from your private pool and terrace. Located in Pyrgos, Vista Dall Alto combines privacy, comfort and easy access to every corner of Santorini. The villa features 2 comfortable bedrooms, 2 modern bathrooms, a fully equipped kitchen and spacious indoor and outdoor living areas. Enjoy complimentary breakfast delivery and daily housekeeping while relaxing by your private pool and enjoying sunset views.

FamilyLocationWalkability

4.98 out of 5 average rating, 264 reviews

An indoor hot tub features calming blue water, framed by a large archway that opens to breathtaking views of the caldera and surrounding landscape. Soft lighting from candles enhances the serene ambiance, complemented by a potted plant placed nearby.

Apartment in Oia

Stellar Sun Suite-1BR/Hot-Tub/Sea View

This elegant suite is perched on the cliffs of the caldera in Oia. It combines traditional Cycladic architecture , making it the perfect choice for those who want to relax. The suite is aprox 37 sm, features a private outdoor cave hot tub, offering privacy along with stunning views of the caldera and volcano. Breakfast is included in the price. The room is equipped with air conditioning, free Wi-Fi, coffee and tea-making facilities, bath amenities, a smart TV and queen size bed.

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A private plunge pool is visible in the foreground, reflecting clear blue water. The stunning caldera view features vibrant blue dome churches in the distance, with the Aegean Sea stretching out toward a clear sky. Whitewashed buildings create a serene backdrop.

4.97 out of 5 average rating, 311 reviews

Santorini blue, caldera views, private pool

Traditional Santorini cave house with famous blue dome churches, postcard perfect caldera views in the heart of Oia. next to main path.. Private plunge heated pool with panoramic views. Next to Island blue, Serenity &Eternity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities Other villas : Island blue, Eternity,Serenity,Captains blue, Secret garden, Sailing &Sky blue Flexible on pandemic related cancellations!

FamilyLocationSleep quality

4.99 out of 5 average rating, 229 reviews

A private terrace features comfortable seating with plush cushions, small wooden table, and decorative bottles. The space provides a clear view of the deep blue ocean and surrounding caldera, complemented by the whitewashed buildings of Oia in the background and a bright blue sky.

Guest suite in Oia

Suite with Blue Domes View

Located in the very heart of Oia, at a secluded position on the famous caldera of Santorini, Oia Spirit is a stylish complex of 8 stand-alone traditional cave houses, with access to a shared cave pool. Right out of a post card between the two iconic blue domes of Oia. This suite has a private terrace with astonishing panoramic view to the caldera and the blue domes. Santorini International Airport is about 17 km from Oia Spirit, and the Ferry Port at approximately 23 km.

ValueFamilyNearby

4.96 out of 5 average rating, 149 reviews

A private patio features a soothing Jacuzzi with sunbeds for relaxation, overlooking the expansive sea and stunning Caldera views. A decorative bowl is placed on a small table beside the Jacuzzi, while soft hues of sunset create a calming ambiance in the background.

Home in Oia

Amazing View Villa Oia with Jacuzzi in Caldera

Hanging over the cliffs of Oia, Amazing View Villa offers uninterrupted views of the Caldera & Volcano islands. Right on the edge of the cliffs, there is a Jacuzzi where you can soak in and enjoy the endless blue view. Perfect for honeymooners & loving couples, Villa consists of 2 levels. You will find a bedroom with a double bed and a bathroom on the higher level. The lower level has a lounge area and access to the yard with the Jacuzzi and breathtaking views.

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4.99 out of 5 average rating, 171 reviews

A private terrace offers a view of the shimmering Aegean Sea, framed by the surrounding caldera cliffs. A plunge pool in inviting turquoise reflects the clear sky. Two elegant flutes stand beside a bowl of fresh fruit, inviting relaxation and enjoyment.

Cave in Oia

Cave Villa With Heated Plunge Pool & Caldera View

A traditional cave villa with modern touches that can accomodate up to four people with spacious veranda and breathtaking caldera views. Lathouri Cave Villa is perched on the famous caldera cliffside overlooking the Aegean sea and the two volcanic islands Palia and Nea Kameni. The traditional cycladic architecture along with the unique scenery makes it the perfect choice for those who want to enjoy a relaxing vacation in the lap of luxury.

FamilyValueBathroom

A private heated jacuzzi is visible in the foreground, offering a stunning view of the caldera and Aegean Sea. The sun sets in the background, casting warm hues across the sky, while rugged cliffs and white buildings are seen along the coast.

4.95 out of 5 average rating, 178 reviews

Blue Sky Suite with jacuzzi and caldera view

The team of Kaleidoscope Cave Houses proudly welcomes two brandly new suites to the Kaleidoscope family in the picturesque Oia village. The Blue Sky Suite, carved into the unique caldera cliff is a fully renovated suite which is located literally in 'the heart' of Oia with breathtaking views over the caldera cliffs and the Aegean Sea. The other listing is the white dome suite with plunge pool and caldera view.

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4.98 out of 5 average rating, 103 reviews

Windmill in Oia

Lioyerma Windmill Villa With Outdoor Hot Tub

At the edge of the traditional settlement of Oia, overlooking the Caldera and the world-famous Oia sunset, stands our fully renovated traditional Windmill, originally built in 1900. This unique three-level residence is connected by internal staircases and can comfortably accommodate a couple with two children or up to four adults. Breakfast is included, and free parking is available for all guests.

FamilyLocationOutdoor spaces

4.96 out of 5 average rating, 159 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.

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Popular amenities for Oia Holiday Accommodation with Breakfast

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with breakfast

4.91 out of 5 average rating, 127 reviews

A serene outdoor terrace features a private jacuzzi surrounded by clean white walls and tiled flooring. Sun loungers are positioned nearby, and a sun umbrella provides shade. The view captures the unique architectural style of Oia, with whitewashed buildings in the background under a clear blue sky.

Home in Oia

Yposkafo Jacuzzi House

ValueFamilyComfort

4.88 out of 5 average rating, 166 reviews

An outdoor terrace features a blue-tiled jacuzzi surrounded by glass railings. Two sunbeds are positioned nearby, accompanied by a small table. Clear skies above highlight the serene and inviting space, ideal for relaxation.

Home in Emporeio

Latipi House

LocationValueKitchen

4.91 out of 5 average rating, 182 reviews

A charming entrance features a light-colored door framed by rustic stone. A small table with tea settings and a decorative potted plant is placed nearby. A window box displays colorful seasonal decorations, complementing the serene atmosphere of the exterior.

Home in Santorini

Nikoletis ,B&B cave house at Arvanitis Village

LocationFamilyAmenities

5.0 out of 5 average rating, 4 reviews

Home in Merovígli

Villa with Pool and Jacuzzi

HospitalityGetting aroundComfort

4.89 out of 5 average rating, 98 reviews

Home in Santorini

Amaranthine Villa

ValueFamilySleep quality

5.0 out of 5 average rating, 62 reviews

A poolside area features a black wire chair and a patterned pouf, overlooking the expansive blue sea and distant island views. The clean, minimalist design highlights the serene atmosphere, while sunlight reflects off the clear water of the pool.

Home in Pyrgos Kallistis

M&D Stories Villa Santorini

LocationFamilySleep quality

5.0 out of 5 average rating, 36 reviews

A traditional cave house exterior is presented with a light-colored facade. A wooden lounge chair is positioned beside a small table, with pots of plants adding to the charm. Coastal views and an expansive sky can be glimpsed in the background.

Home in Agrilia

Sunlight Cave Agrilia

ValueLocationGetting around

4.73 out of 5 average rating, 316 reviews

An open living area is highlighted by a blue seating arrangement and a round wooden coffee table. Decorative items and a wall mirror are visible. Ceiling lights create a bright ambiance, complemented by a stone accent wall. Neutral tones enhance the overall space.

Home in Santorini

3 DAUGHTERS(2)

LocationFamilyBreakfast

Apartment rentals with breakfast

4.97 out of 5 average rating, 191 reviews

A round outdoor table is set on a balcony, accompanied by two white chairs. A bouquet of sunflowers and vibrant red flowers rests on the table, with two colorful glasses nearby. The expansive view of the blue sea and distant islands enhances the tranquil setting.

Apartment in Firostefani

AMAZING STUDIO IN PRIVATE VILLA

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Apartment in Pyrgos Kallistis

The serene private terrace features lounge seating next to a small heated pool, framed by a large yellow awning. Views of the surrounding landscape and distant coastline are visible as twilight descends, creating a peaceful ambiance.

4.85 out of 5 average rating, 144 reviews

Prince Albus Suite with Private Plunge Pool

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4.93 out of 5 average rating, 150 reviews

The image captures a scenic sunset viewed through an arched opening. Soft orange and pink hues adorn the sky, complementing the silhouette of the sea below. A balcony railing painted in blue provides a striking contrast to the white architecture.

Apartment in Merovígli

Peaceful Sunrise Mornings - B&B Apartment

FamilyLocationHospitality

4.92 out of 5 average rating, 139 reviews

A balcony view showcases a vibrant landscape, overlooking the sea and surrounding hills. The table is set with a coffee pot, a yellow cup, orange juice, and fresh fruit, inviting a peaceful moment outdoors. The clear blue sky enhances the overall serene ambiance.

Apartment in Santorini

Crocus apartment minutes walk from caldera

ValueLocationOutdoor spaces

4.98 out of 5 average rating, 57 reviews

A private hot tub is positioned on a terrace, surrounded by smooth stone steps. The panoramic view captures the serene caldera at dusk, with soft hues of orange and blue reflecting in the water. The gentle glow of outdoor lighting enhances the calming evening atmosphere.

Apartment in Oia

Junior Cave Suite at Enalion Suites

LocationValueHot tub

4.98 out of 5 average rating, 47 reviews

A spacious terrace overlooks a serene body of water, featuring a glass railing that enhances the view. Two white chairs and a small table are arranged for relaxation, alongside a decorative plant in a woven basket filled with white stones.

Apartment in Santorini

Cave private suite

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Apartment in Pyrgos Kallistis

An outdoor seating area offers stunning views of the Mediterranean Sea and volcanic landscape. A private Jacuzzi is positioned nearby, surrounded by sun loungers. A couple enjoys refreshments, while one person relaxes in a hanging chair, showcasing the tranquil setting.

4.96 out of 5 average rating, 99 reviews

Honeymoon Suite with Caldera View and Hot Tub

LocationValueHospitality

5.0 out of 5 average rating, 26 reviews

Apartment in Karterados

Aquarill

LocationValueParking

Bed and breakfast rentals with breakfast

A private terrace showcases a hot tub with sweeping views of the sea and surrounding landscape. A cozy lounge area, adorned with patterned cushions, invites relaxation under an archway, while a sunhat rests nearby, complementing the tranquil ambiance.

4.93 out of 5 average rating, 172 reviews

3 Caves suite with Hot-Tub and Caldera View in Oia

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Bed and breakfast in Merovígli

A modern cave suite features a spacious bed with an elegant black and white patterned coverlet. Decorative blue vases and lit candles create a serene ambiance. A small table with decorative items is positioned next to a chair, enhancing the minimalist decor.

4.95 out of 5 average rating, 44 reviews

Thea Cave suite with private terrace and hot tub

LocationValueHeating

4.63 out of 5 average rating, 159 reviews

A spacious outdoor area features a stone patio with a round table and wicker chairs. A swimming pool glimmers under sunlight, surrounded by lounge chairs and thatched umbrellas. The backdrop showcases a mountainous landscape under a clear blue sky.

Apartment in Santorini

House for 4 included car, breakf (Heated Pool)

LocationValueIndoor spaces

4.9 out of 5 average rating, 239 reviews

A serene outdoor seating area features a table surrounded by white chairs and a view of the horizon. A person in a wide-brimmed hat holds a drink, enjoying the atmosphere as soft sunlight bathes the space.

Hotel room

Oia bed and breakfast for 2 & swimming pool

ValueFamilyHospitality

A private terrace features a clear blue Jacuzzi surrounded by inviting sun loungers. An umbrella provides shade, while panoramic views of the Aegean Sea and surrounding landscape are visible under a bright blue sky.

Home in Vourvoulos

4.78 out of 5 average rating, 168 reviews

Tholos Arched Villa, Jacuzzi, Sea View

ValueLocationCleanliness

An expansive outdoor terrace features a pool surrounded by various lounge chairs and seating areas. Lush greenery and terracotta pots are scattered throughout, and stunning ocean views are visible in the background against a clear sky.

Bed and breakfast in Merovígli

4.71 out of 5 average rating, 72 reviews

Belle Etoile villas Santorini

ValueFamilyIndoor spaces

Private room in Merovígli

An outdoor terrace space features a comfortable lounging area with a gray sofa adorned with patterned cushions. A wooden table stands nearby, complemented by a stylish chair. A straw hat and a light throw are casually placed, while the tranquil sea and distant hills are visible in the background.

4.93 out of 5 average rating, 147 reviews

Honeymoon Suite with Outdoor Heated Jacuzzi

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