Vacation rentals in Monolithos

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Top-rated vacation rentals in Monolithos

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Guest favorite

Cycladic home in Pyrgos Kallistis

4.99 out of 5 average rating, 214 reviews

Olyra Traditional Cave Houses

The traditional residences Olyra Traditional Houses, are in the heart of the medievial settlement of Pyrgos, very close to the imposing Kasteli (castle). A three minute walk in the stone laid pavements and side strees is enough to go from Olyra to the central parking of the village as well as the central square. Our houses are created in the same place where the bakery of the village was two centuries ago, with great respect and attachment to Santorinis¨ architecture. The decoration is character

Mar 16 – 23

G$27,368 GYD per night

Guest favorite

Cycladic home in Oia

4.95 out of 5 average rating, 289 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

Dec 17 – 24

G$88,916 GYD per night

Guest favorite

Cycladic home in Oía

4.96 out of 5 average rating, 189 reviews

Helianthus Honeymoon House

Our Honeymoon House with Caldera View offers the perfect romantic escape in Santorini, with the graceful addition of a heated outdoor Jacuzzi (will be closed between 1/11-15/3) providing the ultimate sense of relaxation overlooking the majestic caldera and the infinite Aegean blue. In an ample space of 40m2 divided into two levels, it provides everything a couple may desire. It has been built in perfect alignment with the distinct Cycladic architecture and boasts unparalleled, absolute privacy

Mar 21 – 28

G$144,442 GYD per night

Guest favorite

Guest suite in Oía

4.98 out of 5 average rating, 147 reviews

Suite with Outdoor Plunge Pool & Blue Domes View

Located in the very heart of Oia, at a secluded position on the famous caldera of Santorini, Oia Spirit is a stylish complex of 8 stand-alone traditional cave houses, with access to a shared cave pool. This suite additionally features a private outdoor plunge pool. The view from its terrace is stunning, featuring the caldera and the two iconic blue domes of Oia. Santorini International Airport is about 17 km from Oia Spirit Boutique Residences, and the Ferry Port at approximately 23 km.

Nov 10 – 17

G$90,626 GYD per night

Guest favorite

Apartment in Oía

4.98 out of 5 average rating, 155 reviews

BLUE ART CAVES - Stellar Sun

This elegant and fully renovated suite on 2021, is perched on the cliffs of the caldera in Oia. Combines the traditional cycladic architecture with minimal decorative style makes them the perfect choice for those who wants to relax. The suite has a private indoor/outdoor hottub with caldera and volcano views. Breakfast included in the price and delivered at the accommodation. The room has air condition , free wifi, coffee and tea making facilities, bath amenities and satellite TV.

Jul 21 – 28

G$175,869 GYD per night

Guest favorite

Cave in Thira

4.98 out of 5 average rating, 258 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!

Nov 24 – Dec 1

G$69,459 GYD per night

Guest favorite

Apartment in Oia

4.92 out of 5 average rating, 181 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 12 – 19

G$33,119 GYD per night

Guest favorite

Cycladic home in Oia

4.92 out of 5 average rating, 133 reviews

3 Caves suite with Hot-Tub and Caldera View in Oia

Discover tranquility in the heart of Oia at 3 Caves Villa. This luxurious suite seamlessly blends traditional cave-home charm with modern comforts. With a private terrace boasting a bubbling hot tub and panoramic views of the sea, volcano, and caldera, relaxation is inevitable. Explore Oia's treasures within easy reach, then retreat to your cozy bedroom and sleek bathroom for a restful night. Welcome to your unforgettable Santorini escape.

Aug 10 – 17

G$188,496 GYD per night

Guest favorite

Apartment in Monolithos

4.91 out of 5 average rating, 124 reviews

Tzannis Cave House

In Monolithos, in front of the sea, you will find yourself in a nautical cave of the oldest of the island. The enchanting but also wild beauty of the landscape will travel you and give you nice moments. The cave of Tzannis have a bedroom, a living room with a kitchen and a sofa that can also be used as a bed, bath and yard so that you can sit and enjoy your wine. Within 10 minutes you will find a mini market, taverns and bus stasion.

May 23 – 30

G$25,087 GYD per night

Guest favorite

Cycladic home in Fira , Santorini

4.91 out of 5 average rating, 295 reviews

Divine View Sun Home

Unwind and relax with a glass of wineadmiring the breathtaking views of the famous Santorinian sunset from this house's private veranda . Awake refreshed and ready for a day to explore the island via this clean, sunny house with impressive views to the caldera , volcano of Santorini Aegean Sea & the island of Thirassia . Head out and wander through the famous paths of Fira and explore the nearby little shops & cafe .

Nov 24 – Dec 1

G$19,386 GYD per night

Guest favorite

Cave in Santorini

4.94 out of 5 average rating, 179 reviews

Lava Cave suite 1BR/Private Plunge Pool+Panoramic View

Live the myth by staying in a cave that used to be a sailor's domicile back in 1875. Today after a full restoration, it has been turned into a jewel, keeping its traditional cave-curved Aegean island style with its pearl white walls.

Nov 23 – 30

G$94,507 GYD per night

Guest favorite

Cycladic home in Imerovigli

4.92 out of 5 average rating, 218 reviews

Pura Vida Villa

The Pura Vida Villa is a unique property. The design & construction expertise that have been invested in this property make it one of the unique offerings on the Santorini Caldera. Reserved parking for guests is included.

Oct 18 – 25

G$102,630 GYD per night