Vacation rentals with outdoor seating in Oia

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Top-rated accommodations with outdoor seating in Oia

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Guest favourite

Cycladic homes in Oia

4.95 out of 5 average rating, 292 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

Feb. 28 – Mar. 7

$984 CAD per night

Guest favourite

Cycladic homes in Oia

4.97 out of 5 average rating, 257 reviews

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.

Mar. 7 – 14

$728 CAD per night

Guest favourite

Cave in Thira

4.98 out of 5 average rating, 260 reviews

NK Cave House Villa

The NK Cave House Villa is a modern restoration of a 19th century cave house transformed into a luxury getaway. The one bedroom villa has been designed to offer relaxation and fulfillment, aiming to provide you with the need of returning back in the near future. Situated on the famous caldera, it is perfect for enjoying the spectacular volcanic views and the amazing Santorini sunsets. The villa is a peaceful and tranquil escape even though just a short walk to the center of Fira!

Jan. 22 – 29

$403 CAD per night

Guest favourite

Apartment in Oia

4.92 out of 5 average rating, 183 reviews

Oia Lucky Ruby Residence

Our Ruby Residence offers the perfect romantic getaway in Santorini, with its panoramic views and total privacy, providing the ultimate sense of relaxation overlooking the majestic caldera , world known sunset of Oia and the infinite Aegean blue. In a cozy interior space of 40m2 with a 50m2 private veranda it provides everything a couple may desire. It has been built in perfect alignment with the distinct Cycladic architecture and boasts unparalleled, absolute privacy .

Nov. 18 – 25

$176 CAD per night

Guest favourite

Apartment in Oía

4.99 out of 5 average rating, 101 reviews

Traditional Family Villa with Caldera View

Our Villa, situated just in the heart of Oia, offers a breathtaking view to the Caldera and the Aegean Blue waters. In a walking distance you can enjoy your shoppings as well as all famous restaurants and bars in the area. The villa can comfortably accomodate up to 5 guests, in two spacious bedrooms with double queen size beds each and a sofa bed in the living room area. Air-conditioned with kitchenette and free wi-fi. The balcony offers a dreamy view to the sea.

Mar. 14 – 21

$489 CAD per night

Guest favourite

Cycladic homes in Oía

4.95 out of 5 average rating, 199 reviews

Bluedome Suite by Otium Villas & Suites

This is a newly renovated cavehouse that dates back to the 1890's. Situated in one of the most famous neighbourhood's in Oia "Monastiraki" next to the famous St Spyridon Bluedomes. It has been renovated keeping traditional cycladic cavehouse architecture at the forefront of the design while utilising modern building materials. This suite is ideal for couples and families. Its' minimal designed spaces inspire relaxation and comfort for the modern traveller.

Apr. 17 – 24

$485 CAD per night

Guest favourite

Cycladic homes in Oia

4.83 out of 5 average rating, 226 reviews

Big Blue villa with Hot Tub and Sea View in Oia

Discover unparalleled luxury at our villa in Oia, Santorini. With breathtaking views of the caldera and impeccable design, our spacious accommodations offer a perfect blend of comfort and elegance. Enjoy a private hot tub, attentive hospitality from our dedicated staff, and the convenience of being located in the heart of Oia. Experience the epitome of relaxation and indulgence in this stunning retreat.

Nov. 15 – 22

$629 CAD per night

Guest favourite

Cycladic homes in Oia

4.98 out of 5 average rating, 304 reviews

The Boat Builders House -Oia Center

Built in the late 1800's this is the home of Markos the wooden boat builder. Years ago, the house served as his workshop where he built fishing boats inside what is now the living room, and it later became his family home. He is the only remaining boat builder on the island, who began his craft at the age of 11, down in the port of Armeni just below Oia, and continues to work on the island today.

Oct. 2 – 9

$267 CAD per night

Guest favourite

Apartment in Oia

4.91 out of 5 average rating, 356 reviews

ARGITHEA APARTMENT

My place is close to public transport and the city center. My place is good for couples, solo adventurers, business travelers, and families (with kids). There is a bedroom with a double bed ,a living room with 2 single beds ,a fully equipped kitchen ,a shower room and veranda with perfect view to the sea ,the caldera ,the volcano and the traditional village of OIA .

Dec. 16 – 23

$206 CAD per night

Guest favourite

Cycladic homes in Oia

5.0 out of 5 average rating, 211 reviews

Likno Cave House

With your friends or family, with people dearly loved, enjoy your stay in the Likno Cave House located in the center of the most famous village in Santorini, Oia. Embrace the authenticity and beauty of Santorini in a pure traditional local home with unobstructed caldera views!

Apr. 7 – 14

$515 CAD per night

Superhost

Cave in Oia

4.91 out of 5 average rating, 273 reviews

Skala Cave-by Thireon

Live the ultimate Santorini dream in the heart of world-famous Oia, imbued with the spirit of chic luxury. Perched high atop the caldera cliffs, the infinite views of the glittering sea and sky will take your breath away. A fully serviced property managed by Thireon Houses

Oct. 25 – Nov. 1

$912 CAD per night

Guest favourite

Cave in Oia

4.92 out of 5 average rating, 241 reviews

Pano Meria Cave House One in Oia

A unique cave house built into the face of the cliff overlooking the majestic caldera. Private plunge pool and terrace where you can spend the entire day admiring the views. The epitome of slow living in Oia. Fits up to three people and we can add a fold up bed.

Apr. 11 – 18

$961 CAD per night