Family-friendly vacation rentals in Oia

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

Kitchen · Family · Hot tub

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

Family · Kitchen · Comfort

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.

Indoor spaces · Kitchen · Access

Authentic 2 Bdrm Villa with Plunge Pool & Sea View

Villa Hercules is an authentic 250 year old cave. With the proper renovation it always has the traditional character but all the modern comforts with 2 separate bedrooms. One with a double bed, the other with a king-size bed and 2 single sofa beds. Fully equipped kitchen, WC with shower on the same floor and large bathroom with jacuzzi in the basement. Living room with office corner and dining area. Large private terrace with heated pool, dining area, sunbeds, umbrellas, view.

Kitchen · Family · Check-in

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.

Family · Kitchen · Checkout

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.

Family · Kitchen · Outdoor spaces

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.

Kitchen · Family · Decor

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.

Indoor spaces · Kitchen · Location

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.

Family · Indoor spaces · Getting around

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!

Kitchen · Indoor spaces · Comfort

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.

Family · Indoor spaces · Checkout

Armeni Beach House - with private boat service!

Delve into the soul of the caldera by staying in this beautiful and cosy beach house, nestled in Armeni Bay, the hidden gem of Oia! Accessed either on foot through 300 steps, or by our private boat service. Perfect for those with adventurous mind and energy!

Family · Indoor spaces · Parking