Family-friendly holiday rentals in Oia

4.95 out of 5 average rating, 119 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

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, 310 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!

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.

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.

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.

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.

4.96 out of 5 average rating, 157 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.

4.99 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!

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

Discover the real Santorini, beyond the crowded touristic routes. Mayia Cave House is a renovated 19th century traditional cycladic cave house in the quiet medieval village of Pyrgos. Offers all modern amenities, a spectacular private large warmed cave pool, a private hot tub in the terrace and incredible views over Santorini, including the famous sunset.

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.

A view is presented through wide-open windows, offering a glimpse of the expansive sea and caldera. A wooden dining table is visible on the terrace, surrounded by natural scenery. Bright clouds fill the sky, enhancing the serene atmosphere of the coastal landscape.

5 out of 5 average rating, 270 reviews

Likno Traditional Villa

With your friends or family, with people dearly loved, enjoy your stay in the Likno Traditional Villa located in the center of the most famous village in Santorini, Oia. Experience the most astonishing caldera views with the comfort of a traditional local home, your home in Santorini!

4.93 out of 5 average rating, 415 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

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 terrace features a hot tub surrounded by a scenic view of the ocean and distant cliffs. Two black woven chairs and a round wooden table create a cozy seating area, while a lantern adds subtle illumination, perfectly complementing the serene atmosphere.

4.87 out of 5 average rating, 108 reviews

Panoramic Suite | Outdoor Hot Tub | Caldera View

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

Place to stay in Imerovigli

4.95 out of 5 average rating, 155 reviews

Esmi Suites 2 Private Outdoor Jacuzzi Sunset View

5 out of 5 average rating, 159 reviews

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.

Villa in Oia

Loukia House

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)

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

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.

4.98 out of 5 average rating, 263 reviews

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

4.92 out of 5 average rating, 351 reviews

Cave in Oia

Skala Cave-by Thireon

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

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.

4.94 out of 5 average rating, 288 reviews

Blue Mirage

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

4.98 out of 5 average rating, 391 reviews

Historic Boatbuilder's House - Sunset Terrace Oia

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

4.97 out of 5 average rating, 201 reviews

Villa in Oia

Luxury Villa | Outdoor Hot Tub | Sea & Sunset View

Superhost

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

4.89 out of 5 average rating, 142 reviews

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, 271 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, 234 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.

4.96 out of 5 average rating, 201 reviews

Infinity Pool • Luxury Villa • Sea View

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

4.99 out of 5 average rating, 107 reviews

A spacious terrace is highlighted with a white bench facing the calming Aegean Sea. The horizon features a gentle sunset, casting warm hues of orange and pink across the sky. Silhouetted mountains can be seen in the distance, enhancing the serene atmosphere.

Villa in Santorini

Anemi Villa - Sunset and Sea Views

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

4.83 out of 5 average rating, 100 reviews

Deluxe Suite with Plunge Pool @Aplada Suites

4.96 out of 5 average rating, 355 reviews

A private outdoor space features a plunge pool, small table, and two chairs. Bright beverages sit atop the table beside towels. The scene includes whitewashed walls, and expansive views of the deep blue sea and surrounding islands under a clear sky.

Cave in Santorini

Hector Cave House

A private non-heated splash pool is positioned on a terrace with a view of the ocean and distant hills. Surrounding the pool, decorative stones and a straw hat add a relaxed touch to the inviting space. Bright sunlight reflects off the water's surface.