Family-friendly vacation rentals in Oia

A private heated pool is seen on a terrace, offering unobstructed views of the deep blue sea and distant islands. The scene includes iconic white buildings with blue domes, set against a clear sky, showcasing typical Santorini architecture.

4.95 out of 5 average rating, 397 reviews

Island blue, postcard perfect view & private pool

Traditional cave house located in the most famous location in Santorini Island with breathtaking postcard perfect views of the blue domed churches! 2 bedrooms, double beds 2 cave bathrooms. Outdoor heated pool with view! Next door to Santorini blue, Eternity & new home Serenity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities. Our other villas Santorini blue,Eternity,Serenity,Captains blue, Secret garden,Sailing & Sky blue

4.99 out of 5 average rating, 165 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 Imerovigli

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.

4.99 out of 5 average rating, 221 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.

A tranquil outdoor jacuzzi is visible, with a view of iconic blue-domed structures nearby. The sun casts a warm glow, reflecting on the water. The serene ambiance is enhanced by the surrounding landscape, suggesting a peaceful retreat in a picturesque setting.

4.99 out of 5 average rating, 167 reviews

Santo Blue Horizon Villa | Jacuzzi | Caldera View

This unique villa is located in the heart of Oia in an excellent position and has stunning views. The famous Three Domes just in front of villa with panoramic view overlooking the santorinian caldera and the aegean sea, have magnetized visitors and photographers from all over the world, making it, the most popular spot in Santorini. The villa is in perfect harmony with the natural surroundings of the area and follows the principles of traditional Cycladic architecture.

A private balcony features lounge seating and planters filled with greenery, overlooking the iconic white buildings of Santorini. A serene sunset casts warm hues over the horizon, reflecting softly on the water, creating a calm and inviting ambiance.

4.99 out of 5 average rating, 273 reviews

Anemi Karma- Private Villa with Sunset Views !

Anemi Karma House, our new part of our collection, is a Traditional Cycladic Cave House, located at the best spot in Santorini, to watch the breathtaking Sunset Views at the comfort and privacy of your balcony! Enjoy and revive, at our Anemi Karma House , upgrading your Holidays to an experience,as Dimitris, the Host, is very famous for his great Greek Hospitality offering high end tailor made services! We are looking forward to welcome you to our paradise!

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.

4.99 out of 5 average rating, 157 reviews

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.

4.93 out of 5 average rating, 160 reviews

Townhouse in Oia

"Our Grandma’s spacious House" in Oia, Santorini

"Grandma's House" offers a serene retreat for your holiday in Oia, ideal for digital nomads and writers. This spacious Venetian-style Captain's Mansion is perfect for families or couples seeking relaxation, as well as adventurous groups of up to eight looking for an affordable stay. Facing north towards the open sea, the house is just 50 meters from the main square, grocery shops, takeaways, and the public bus terminal.

4.99 out of 5 average rating, 198 reviews

By the Mill, Caldera, Oia

100 sq meters of traditional cave house - 3 bedrooms and 3 bathrooms, spread over 3 levels of 100 square meters of private terraces and private plunge pool. At Oia's heart - incredible volcano, caldera & sunset views all year round. Easy access, and remarkable privacy, as well as daily housekeeping and plunge pool maintenance.... By the Mill is your dream Santorini home!

A scenic view showcases traditional Cycladic architecture with whitewashed structures and striking blue domes. In the foreground, a quiet outdoor space features a small table set with fruit, while the expansive Aegean Sea and volcanic caldera are visible in the background under a clear blue sky.

4.97 out of 5 average rating, 130 reviews

Evmenia Luxury Cave Villa

Evmenia Luxury Cave Villa is a spacious (75 sq. m.) self-catered home located right in the heart of the traditional settlement of Oia. The villa has a (25 sq. m.) private patio which offers an unobstructed, gorgeous, panoramic view of the magnificent Caldera and the unique crystal clear waters of the Aegean Sea.

4.92 out of 5 average rating, 405 reviews

A panoramic view captures the deep blue sea contrasting with the rugged cliff, dotted with white buildings and blue-domed roofs. A cruise ship glides smoothly across the water, while the picturesque landscape of the caldera extends toward the horizon.

Home in Oia

VILLA MATILDE-VOLCANO VIEW

VILLA MATILDE in Santorini sits on the edge of the Caldera in Oia.A charming Cycladic house, with typical domed roofs and high ceilings, VILLA MATILDE is spacious enough to accommodate 6 or 7 people.2 bedrooms, sofa beds at the living room,2 showers

A balcony overlooking the caldera features two wooden chairs facing the sea, accompanied by a round table. Refreshments are placed on the table, with the vast ocean and distant islands visible in the background, and a plant sits nearby, adding a touch of greenery.

4.95 out of 5 average rating, 349 reviews

Pano Meria Cave House 3 in Ia

This is a renovated cave situated in Oia. It can sleep between 2 and 4 guests it has 2 doubles. It also has self-catering facilities. It is in the old part of the village and has a balcony overlooking the caldera. Quiet and peaceful but central.

4.95 out of 5 average rating, 253 reviews

An indoor-outdoor Jacuzzi is illuminated by candles, with soft blue water inviting relaxation. A panoramic archway frames a tranquil view of the sea, while a glass of red wine and a plate of grapes are presented nearby.

Cave in Santorini

Lava Cave suite 1BR/Private Plunge Pool+Panoramic View

Live the myth by staying in a cave that used to be a sailor's domicile back in 1875. Today after a full restoration, it has been turned into a jewel, keeping its traditional cave-curved Aegean island style with its pearl white walls.

Popular amenities for Oia family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An outdoor private jacuzzi is positioned on a spacious deck, surrounded by two lounge chairs made of natural wicker. Stunning views of the Caldera gulf and distant islands are visible against a clear blue sky, creating a serene setting.

4.97 out of 5 average rating, 308 reviews

Aspa Caves studio, outdoor hot tub & caldera view!

A view from the terrace features a custom-built hot tub with clear water, surrounded by whitewashed walls. In the background, a traditional blue-domed church tower stands prominently against a serene sea and sky, capturing the charm of the Oia landscape.

4.96 out of 5 average rating, 248 reviews

Blue Dome Suite by Otium Villas Santorini

4.95 out of 5 average rating, 100 reviews

A spacious terrace is presented with a comfortable seating area featuring a lounge sofa and a table set for two. A glimmering private jacuzzi is visible nearby, surrounded by sleek tiled flooring and unobstructed views of the Aegean Sea and landscape.

Dome in Oia

Casa paradiso private villas

Cycladic home in Santorini

The image presents a view of a traditional white structure topped with a vibrant blue dome, characteristic of Santorini architecture. In the background, the expansive caldera stretches into the horizon, complemented by gentle waves and the silhouette of landmasses under a clear sky.

4.98 out of 5 average rating, 213 reviews

Luxurious Amara Villa: Unmatched Imerovigli Views

4.98 out of 5 average rating, 253 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

4.95 out of 5 average rating, 151 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 Exclusive Suites

4.98 out of 5 average rating, 244 reviews

An outdoor terrace offers a jacuzzi and comfortable seating, perfect for relaxation. Expansive views of the caldera and surrounding landscape are visible, showcasing the natural beauty of Santorini. The clean, modern layout encourages outdoor enjoyment while highlighting the tranquil setting.

Cycladic home in Fira

Sol

4.95 out of 5 average rating, 147 reviews

Cycladic home in Fira

Revelis Villa

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 247 reviews

A serene outdoor terrace features a heated plunge pool, surrounded by comfortable loungers. The vibrant colors of the sunset illuminate the sky and reflect on the calm waters of the Aegean Sea, offering a tranquil atmosphere for relaxation.

Villa in Imerovigli

Entire Private Antrum Villa with Jacuzzi sunset

4.94 out of 5 average rating, 275 reviews

A small white table is set on a balcony with a blue tablecloth and two glasses, overlooking a calm sea. A bottle of wine sits on the table, with views of distant islands visible under a clear sky.

Apartment in Oia

Blue Mirage

Cycladic home in Santorini Island

An inviting living space features a vintage wooden armoire beside a potted plant with large green leaves. A cozy sleeping area is visible through an archway, with a light-colored quilt spread over a spacious bed. A retro-style refrigerator adds a charming touch to the kitchen area.

4.99 out of 5 average rating, 293 reviews

Sunset Views From Sideras House in Oia Center

4.9 out of 5 average rating, 103 reviews

The image showcases a cave-style heated pool with serene blue water. Soft lighting highlights the smooth white walls and ceiling, creating a calm ambiance. A wooden bench is positioned nearby, and a glass door leads to additional living spaces, enhancing the inviting atmosphere.

Dome in Episkopi Gonias

Aleria Luxury Cave Santorini - private heated pool

A private plunge pool is showcased beneath a bright blue sky, with expansive views of the shimmering sea and distant islands. Lush greenery and a cactus are visible near the pool, adding natural elements to the serene outdoor space.

4.94 out of 5 average rating, 390 reviews

Sunset Cave House by Spitia Santorini

An outdoor seating area is featured under a wooden pergola, providing shade and comfort. Two orange chairs are placed near a small table, surrounded by vibrant flowers and greenery. The entrance to the home is visible through a large glass door, complemented by a nearby window.

4.9 out of 5 average rating, 104 reviews

Absolute peace south villa a place to chill

4.9 out of 5 average rating, 138 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

An outdoor terrace features a private hot tub surrounded by neutral tiles. A small round wooden table and two chairs are positioned nearby, offering a space to relax. The background showcases soft, earthy tones of neighboring buildings against a cloudy sky.

4.83 out of 5 average rating, 268 reviews

Lovely House at Oia Village Center

Family-friendly home rentals with a pool

Cycladic home in Akrotiri

An infinity pool with crystal-clear water reflects the serene sky, framed by a curved architectural feature. The pool seamlessly blends into the view of the caldera and volcanic islands, providing a tranquil setting for relaxation.

5 out of 5 average rating, 221 reviews

Anemos suite -Private infinity pool & patio

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.

4.95 out of 5 average rating, 194 reviews

Vista Dall Alto | Sunset Views & Private Pool

4.9 out of 5 average rating, 167 reviews

An outdoor terrace showcases a natural wood table surrounded by comfortable seating. Morning refreshments, including pastries and drinks, are presented on the table. A clear blue sky and distant ocean views complement the serene ambiance of the space.

Home in Θήρα

STILVI SUITE

The image captures a serene nighttime view of Oia village, illuminated by soft lights reflecting off buildings along the cliff. In the foreground, a jetted plunge pool is visible, showcasing a clear water surface, inviting relaxation against the backdrop of the twinkling village.

4.91 out of 5 average rating, 101 reviews

Aqua Terra private villa on the cliff

Cycladic home in Imerovigli

An outdoor area showcases a serene pool surrounded by sun loungers. A shaded cabana adds a touch of elegance, while panoramic views of the Aegean Sea stretch into the horizon under a clear blue sky.

4.9 out of 5 average rating, 142 reviews

"Dream Home" Master Villa

4.81 out of 5 average rating, 232 reviews

Villa in Oia

Amazing views of volcano, private pool, spacious

4.98 out of 5 average rating, 213 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.

Apartment in Fira

Saints Apostles Villa with private pool