Family-friendly holiday 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, 409 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

KitchenIndoor spacesAir conditioning

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 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.

Indoor spacesKitchenAmenities

4.95 out of 5 average rating, 121 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

Casa Paradiso is a brand-new property featuring five luxurious, autonomous, and private villas, located in the heart of Oia, Santorini. We offer the perfect blend of luxury, relaxation, and top-quality services, just a 6-minute walk from the magnificent caldera and world-famous sunset views. Just a short distance from the center of Oia, with its breathtaking views, the village's restaurants and bars are only a 7-minute walk away. Enjoy complete privacy while being in the heart of Oia

Indoor spacesKitchenNearby

4.99 out of 5 average rating, 110 reviews

A heated mini pool is situated within a cave-style space, illuminated by soft light from surrounding fixtures. An archway frames a view of the sea, with calming turquoise water reflecting the gentle lighting, creating a relaxing environment.

Cycladic home in Fira

Revelis Canava

Revelis Canava is a beautiful cave style villa situated right in the center of Fira but still away from the crowed spots. In a spacious and cozy environment you will be able to relax and enjoy the island of Santorini. The terrace, with the lounge area and the heated mini pool, is the ideal spot to watch the spectacular view that the Caldera offers, fantastic sunset colors and relaxing scenery. The second bedroom which is a cave bed as well as the pool are ideal for children.

FamilyIndoor spacesView

4.92 out of 5 average rating, 310 reviews

An outdoor seating area is highlighted by a coffee table surrounded by soft, white lounge chairs. A private jacuzzi can be seen in the background, with a stunning view of the blue ocean and distant islands. A pergola provides shade, enhancing the relaxing atmosphere.

Dome in Fira

Fira White Residence Deluxe Villa

A fully-equipped villa with an attic. With its wide veranda [40m²] and the irresistible combination of stone - exterior and modern - interior, it accomplishes the perfect mix & match of the local traditional architectural style with the most modern touches. It is made up of two bedrooms, the first one [14m²] being carved in the heart of a Santorinean rock, with a concrete bed, commodes and a TV set, and the second bedroom [12m²] featuring a black iron bed with commodes.

FamilyIndoor spacesOutdoor spaces

A tranquil outdoor area features a custom hot tub accompanied by two lounge chairs. A panoramic view of the blue sea and cliffs is visible, complemented by iconic blue-domed buildings in the background. The scene is well-lit under clear blue skies.

4.88 out of 5 average rating, 268 reviews

Bluedome Cavehouse by Otium Villas Santorini

Luxury Cavehouse in Oia | Caldera Views | Heated Jacuzzi | Sleeps up to 6 Wake up to breathtaking caldera and Aegean Sea views from the private terrace of Bluedome Cavehouse, a spacious luxury cave villa in the heart of Oia, Santorini. Blending authentic Cycladic architecture with modern comfort and design, this beautifully renovated cavehouse offers an unforgettable retreat for couples, families, and small groups seeking romance, privacy, and panoramic sunsets.

Indoor spacesFamilyHot tub

4.99 out of 5 average rating, 170 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.

KitchenIndoor spacesHiking

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.

KitchenIndoor spacesBreakfast

4.96 out of 5 average rating, 158 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.

KitchenIndoor spacesBreakfast

4.99 out of 5 average rating, 207 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!

FamilyKitchenLong stay

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, 135 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.

KitchenFamilyNearby

4.92 out of 5 average rating, 115 reviews

An outdoor terrace overlooks the calm sea, featuring an inviting jacuzzi surrounded by seating and potted greenery. The view reveals the blue water and dramatic cliffs of Santorini, with white-washed buildings visible on the hillside.

Home in Oia

Archon Villa by K&K (outdoor jacuzzi)

ARCHON VILLA by K&K lies on a beautiful spot in Oia's caldera, with a breath taking view to the volcano and Santorini's fierce beauty. It features 2 bedrooms, 2 bathrooms, a living room, a kitchen, a terrace and an outdoor jacuzzi. Enjoy all the island has to offer from this stunning house.

FamilyKitchenLayout

Popular amenities for Oia family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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

KitchenIndoor spacesBreakfast

Place to stay in Imerovigli

4.95 out of 5 average rating, 155 reviews

Esmi Suites 2 Private Outdoor Jacuzzi Sunset View

KitchenIndoor spacesHospitality

4.88 out of 5 average rating, 117 reviews

An intimate outdoor dining setup is seen on a private terrace, featuring a small table for two beside a plunge pool. Candles illuminate the area, casting a warm glow against the backdrop of the caldera and Oia's iconic architecture at sunset.

Cave in Oia

The Blue Domes Cave House by Spitia Santorini

Indoor spacesFamilyQuiet

4.98 out of 5 average rating, 263 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

Indoor spacesFamilyHot tub

4.98 out of 5 average rating, 148 reviews

Home in Oia

Ambi, Authentic Cycladic Cave Villa | Caldera View

FamilyKitchenOutdoor spaces

4.92 out of 5 average rating, 351 reviews

Cave in Oia

Skala Cave-by Thireon

Indoor spacesFamilyCleanliness

Place to stay in Vothonas

A private indoor cave pool is set within a smooth, naturally formed alcove, with gentle lighting reflecting off the water’s surface. A staircase is visible in the background, leading to a brightly lit area, enhancing the cave's unique ambiance.

4.96 out of 5 average rating, 292 reviews

Mystagoge Retreat with subterranean pool/jacuzzi

Indoor spacesFamilyHospitality

Cycladic home in Pyrgos Kallistis

An illuminated cave pool is surrounded by smooth curves of stone walls, highlighting the modern design. The warm water reflects soft blue tones, creating a serene ambiance in the space. An indirect light source enhances the unique features of the pool area.

4.96 out of 5 average rating, 302 reviews

Santorini Mayia Cave House with Private Cave Pool

FamilyKitchenDecor

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 257 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

KitchenFamilyCheckout

4.94 out of 5 average rating, 288 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

Indoor spacesFamilyLocation

4.98 out of 5 average rating, 189 reviews

A modern villa is presented with a distinctive white dome roof, surrounded by greenery and blue sea views. A shaded patio features sun loungers beside a small swimming pool, providing a relaxing outdoor space. The bright blue doors complement the serene landscape.

Dome in Oia

MyBoZer Twins Odyssey Heated private pool

FamilyIndoor spacesGetting around

4.98 out of 5 average rating, 391 reviews

Historic Boatbuilder's House - Sunset Terrace Oia

FamilyKitchenHiking

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

FamilyKitchenLocation

4.95 out of 5 average rating, 228 reviews

A cozy sleeping area is defined by a spacious bed dressed in neutral tones and an intricately patterned blanket. The cave walls feature a natural rock formation, adding character. A small wooden table is positioned beside the bed, providing a homey touch.

Earthen home in Emporio

Traditional Farmers Secret Cave#1 Santorini

KitchenFamilySolo travel

A terrace overlooks the Aegean Sea, featuring a heated jacuzzi alongside elegant seating. The sun sets on the horizon, casting a warm glow over the space. Nearby guests are seen enjoying the scenic view, enhancing the inviting atmosphere of the location.

4.84 out of 5 average rating, 160 reviews

Sunset villa in Oia

KitchenIndoor spacesAccess

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, 271 reviews

Lovely House at Oia Village Center

FamilyIndoor spacesDecor

Family-friendly home rentals with a pool

Cycladic home in Akrotiri

An infinity pool gently merges with the shimmering caldera below, framed by an elegant archway. The water reflects a tranquil blue, inviting relaxation while offering sweeping views of the volcanic landscape that surrounds.

5 out of 5 average rating, 234 reviews

Anemos suite -Private infinity pool & patio

Indoor spacesKitchenOutdoor spaces

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, 201 reviews

Infinity Pool • Luxury Villa • Sea View

KitchenIndoor spacesHot tub

4.91 out of 5 average rating, 172 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

Indoor spacesKitchenHot tub

An outdoor dining area is positioned under a shaded pergola, with a wooden table and white chairs arranged for evening meals. The pool reflects the colorful sunset, with scenic views of the caldera visible in the background.

4.91 out of 5 average rating, 100 reviews

Villa Polaris Oia with Volcano view, Pool &Parking

Indoor spacesKitchenQuiet

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

FamilyKitchenGetting around

4.98 out of 5 average rating, 225 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

Indoor spacesKitchenCheck-in

4.83 out of 5 average rating, 101 reviews

Apartment in Oia

Deluxe Suite with Plunge Pool @Aplada Suites

Indoor spacesKitchenValue