Pet-friendly vacation rentals in Oia

Villa in Pyrgos Kallistis

An outdoor space features two lounge chairs facing an infinity pool that overlooks the sea. Lush greenery surrounds the area, while a clear sky adds brightness to the scene. The pool reflects the serene blue of the water, creating a tranquil atmosphere.

4.99 out of 5 average rating, 114 reviews

Santorini Sky | Panoramic Villa *NEW*

SPECIAL 2025 RATES. BOOK NOW! As seen in Vanity Fair, Conde Nast Traveller and Architectural Digest, this amazing villa will take your breath away. With panoramic windows in every room, a large private terrace with infinity pool, and a separate heated jacuzzi, you can enjoy incredible sea views from sunrise to spectacular sunset. This is paradise! Includes complimentary access to our Sky Lounge, with breakfast pantry items and snacks throughout the day. Contact us today with any questions!

4.97 out of 5 average rating, 290 reviews

A view of a private terrace showcases the sea and caldera beyond. A small round table with two chairs is positioned outside, while a whirlpool bath is visible in the foreground, framed by arched windows that enhance the bright atmosphere.

Cave in Oia

Historic cave house, the old bakery by Cycladica

The old bakery of the village awaits just two minutes from Oia's central square, with a private entrance right on top of the stairs that lead to Armeni bay. Carved in the mountain with respect to the unique local architecture and in harmony with the sun-filled, wild volcanic beauty, the newly restored cave house recounts stories of tradition, heritage and style. The red pumice stones, antique marble floors and handcrafted wooden furniture, create the feeling of an authentic warm hospitality.

Superhost

A balcony offers stunning views of the Caldera, featuring a small table with colorful plates set for two. The bright sun reflects on the calm blue waters, creating a serene atmosphere. White walls and a dark door frame complement the inviting outdoor space.

4.88 out of 5 average rating, 113 reviews

Aerie House in Oia

Aerie is a beautiful 85 m2 house, uniquely restored, located in the heart of Oia. It is consisted of two different spaces, layed out in 2 floors: the main house, with a big living room, fully equipped kitchen, one bedroom, a convenient dressing room and a small cave loft, as well as a separate room on top of it, which is accessed through it's own entrance. They both share the same cosy, private yard and a balcony with an astonishing view of the Caldera. It can accommodate up to 6 people.

4.95 out of 5 average rating, 156 reviews

A clear view of the sea is framed by two arched windows, displaying the tranquil water and sun loungers on a stone patio. The interior features light-colored walls and wooden shutters, enhancing the open and airy feel of the space.

Cave in Red beach

Cueva del Pescador

Enjoy two luxurious, newly-remodeled cave dwellings only two meters from the sea: Cueva de olas and Cueva del pescador! These gorgeous spaces are perfect for discerning honeymooners, couples, or anyone who wants to take a break from the real world -- and from the typical tourist traffic of Santorini. Cueva de olas was originally the residence of a local fisherman; Cueva del pescador was his boat-house. Traditional decor and outstanding hospitably complete this perfect, unique rentals!

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, 247 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!

4.95 out of 5 average rating, 376 reviews

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.

Cave in Oia

Sunset Cave House by Spitia Santorini

Embrace the quintessential Santorini experience at the Sunset Cave House, a magical retreat carved into the volcanic rock of Oia's caldera cliff. This traditional yet luxuriously appointed accommodation offers unparalleled panoramic views of the Aegean Sea and the world-famous Oia sunset from your private outdoor plunge pool. Accommodating up to 3 guests, it promises an intimate and unforgettable stay where every moment is bathed in the island's unique light.

A couple is seated on a comfortable chair, enjoying a sunset view over the calm sea. The vibrant colors of the sky blend into soft oranges and yellows as the sun descends. A decorative shell sits on the balcony, enhancing the serene setting.

4.81 out of 5 average rating, 129 reviews

Anima Residence By K&K (outdoor jacuzzi)

Anima Residence is a traditional fisherman's house with local architecture and an impeccable view.Enjoy the direct sunset & caldera view from your private balcony with outdoor hot tub.This is a totally private villa that can comfortably accommodate up to 6 guests. It has 3 bedrooms, 1 bathroom and a fully equipped kitchenette. Anima Residence is just above Ammoudi beach and in the centre of Oia where you can find numerous shops and restaurants.

A private terrace features potted plants against a backdrop of the caldera and sea. A plunge pool is visible, with steps leading away toward the water. In the distance, a wooden boat floats peacefully on the calm blue water.

4.99 out of 5 average rating, 180 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 Exo Gonia

A spacious balcony features an externally heated jacuzzi, illuminated by subtle lighting. The moon casts a gentle glow over the serene sea and distant coastline, while a muted landscape is visible in the background, creating a tranquil nighttime atmosphere.

4.98 out of 5 average rating, 110 reviews

Terra e Lavoro Suite with Hot Tub & Sea View

The exceptional space of Terra e Lavoro in Santorini was ideally designed to offer a personalized experience of enjoyment to those seeking a luxurious retreat on their vacation. The Terra e Lavoro luxurious apartment in Exo Gonia is a modern Villa in Santorini with traditional architecture, ready to welcome its guests and lead them to unique moments of relaxation.

4.95 out of 5 average rating, 178 reviews

A sunlit terrace overlooks the sparkling sea, featuring a hot tub and a red dining table surrounded by black chairs. Sun loungers are positioned along the edge, with the volcanic cliffs and distant islands visible in the background.

Cave in Oia

Satori Caves by Thireon

Welcome to Satori-where the glittering sea meets the endless sky at the top of Oia’s breathtaking volcanic cliffs. The house i has an amazing terrace with hot tub for your own private volcano viewing spot! , there are very few steps to climb to reach this caldera home rewarding you with PRIVACY and away of the crowds. Managed by Thireon Houses

4.98 out of 5 average rating, 205 reviews

A serene exterior of a twin villa is depicted at night, highlighting the soft glow of warm lighting from the windows. A swimming pool can be seen, reflecting the calm ambiance, surrounded by lush greenery and a landscaped area.

Dome in Oia

MyBoZer Twins Iliad Private pool

Our brand new My Bozer twin summer villas are located by the sea, right at the entrance of the famous Oia village. Villa Iliada & Odyssey can host couples, families or group of friends, offering all necessary amenities that will guarantee a relaxed, private holidays in the most beautiful place on earth, Santorini island!