Vacation rentals in Paralia Monolithos

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Top-rated vacation rentals in Paralia Monolithos

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Guest favorite

Cylindrical blue domes top whitewashed buildings, overlooking the Aegean Sea. A private heated pool showcases stunning views of the caldera and rocky landscape. In the foreground, a person relaxes in the water, with clear skies above enhancing the serene atmosphere of the location.

Cycladic home in Oia

4.95 out of 5 average rating, 347 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

Top guest favorite

An outdoor terrace features a sun lounger positioned next to an infinity pool, extending towards the sea. Soft towels are rolled and placed on the lounger, while the horizon showcases a gentle blend of ocean blues under a clear sky.

Villa in Pyrgos Kallistis

4.99 out of 5 average rating, 112 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!

Guest favorite

A view from a shaded archway displays the iconic blue dome of a nearby church, framed by whitewashed traditional architecture. A sunlit terrace features inviting seating with blue cushions and offers glimpses of the caldera and surrounding landscape.

Guest suite in Oia

4.98 out of 5 average rating, 192 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.

Guest favorite

An outdoor terrace features a wooden table set for two, accompanied by modern chairs. The view includes calm blue waters and gentle waves, framed by a structured overhang that provides shade. Sunlight casts shadows, enhancing the serene coastal atmosphere.

Cave in Red beach

4.91 out of 5 average rating, 143 reviews

Cueva de Olas

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!

Guest favorite

An exterior view reveals a light-colored entrance leading into the villa. The sleek door opens to a stairwell. Above, the bright sky is dotted with clouds, while the hillside showcases a collection of white buildings and rooftops typical of Oia.

Home in Oia

4.96 out of 5 average rating, 117 reviews

Amazing View Villa Oia with Jacuzzi in Caldera

Hanging over the cliffs of Oia, Amazing View Villa offers uninterrupted views of the Caldera & Volcano islands. Right on the edge of the cliffs, there is a Jacuzzi where you can soak in and enjoy the endless blue view. Perfect for honeymooners & loving couples, Villa consists of 2 levels. You will find a bedroom with a double bed and a bathroom on the higher level. The lower level has a lounge area and access to the yard with the Jacuzzi and breathtaking views.

Guest favorite

Cycladic home in Monolithos

4.94 out of 5 average rating, 153 reviews

Sea & Sky Luxury Beach House

This elegant and comfortable, newly renovated studio in the traditional Cycladic style, is located right by the beach of Agia Paraskevi. In a quiet area, away from the crowds and noise, it makes a perfect location for those who wish to have a relaxed and private vacation. While offering the advantage of tranquillity, the studio is also only 10-15 minutes on foot from the Kamari area which features a multitude of restaurants, coffee shops as well as other stores.

Top guest favorite

A shared swimming pool is set against a backdrop of stunning sea views. The pool features a clear, inviting blue water, with metal steps leading in. Surrounding the area are light-colored walls and terraces that enhance the open space, complemented by a clear blue sky.

Apartment in Pyrgos Kallistis

5 out of 5 average rating, 189 reviews

Star Infinity Suite with private heated Jacuzzi.

Star Santorini Infinity Suites is brand new complex of 3 suites each one with private heated jacuzzi and one shared swimming pool. An exclusive location provides a marvelous seashore&mountain landscape. This Suite is with two bedrooms (one bedroom is loft style bedroom). Two bathrooms,one living area with kitchenette,two balconies,one private jacuzzi and one shared swimming pool.Greek breakfast (only from local fresh products) is served every morning.

Top guest favorite

Apartment in Monolithos

4.91 out of 5 average rating, 129 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.

Top guest favorite

An infinity pool reflects calming waters, seamlessly merging with the horizon. The sunset casts soft hues of orange and pink across the sky, while rolling hills and distant islands create a serene backdrop. The curve of the suite architecture frames this tranquil view.

Cycladic home in Akrotiri

5 out of 5 average rating, 187 reviews

Akrorama Anemos - Private Pool & Caldera View

Anemos suite is located in Akrotiri overlooking the caldera and the volcanic islands . It is a suite with Private, Infinity heated Cave style plunge pool with Jet system and private patio. There is a king size bed that can accommodate two person. Daily breakfast is included and served in your suite . There is a cleaning service included. Inform us about your arrival details in advance , we can arrange a taxi/transfer for you.

Guest favorite

Cycladic home in Santorini

4.9 out of 5 average rating, 200 reviews

Helianthus Honeymoon Cave Home

Our Prestige House is ideal for a memorable holiday experience in Oia. In its 50 square meters, the suite encompasses authentic Theran architecture with a modern twist . The heated outdoor Jacuzzi (it will be closed for the period of November 15th till March 15th) offers you the opportunity to dip in the water and enjoy the laid-back atmosphere and the stunning views to the deep blue sea , the volcano and the caldera!

Top guest favorite

A private outdoor terrace features a round table with a fruit bowl and two white chairs, overlooking expansive views of the Aegean Sea and surrounding islands. Subtle greenery is visible in planters, complemented by a clear blue sky and distant volcanic landforms.

Cycladic home in Fira

4.93 out of 5 average rating, 418 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 .

Guest favorite

Home in Imerovigli

4.96 out of 5 average rating, 122 reviews

Esmi Suites Santorini 1

Welcome to the world of Esmi Suites in Imerovigli , Santorini. If you are truly indulgent getaway where you can unwind and rejuvenate in style , Esmi Suites is the epitome of relaxation and bliss . Nestled in the picturesque village of Imerovigli , perched on the volcanic cliffs overlooking the Aegean Sea . Our Suites offer unique and unforgettable experience for discerning travelers seeking a slice of paradise.

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Other great vacation rentals in Paralia Monolithos

A clear blue sky is visible above the private outdoor jacuzzi, which is partially filled with water. The smooth white surface of the jacuzzi contrasts with the surrounding minimalistic design. An open door leads into the interior space, inviting guests to enjoy both indoor and outdoor relaxation.

Home in Pyrgos Kallistis

5 out of 5 average rating, 3 reviews

Maison Kallisti • Private Jacuzzi & Panoramic View

IlektraRating, 5 stars1 week ago

We had a fantastic stay at this spacious Airbnb! The home was clean, comfortable, and perfect for our group of friends. There was plenty of room for everyone to relax and enjoy themselves, and the common areas were great for hanging out together. The host was responsive and made everything easy from check-in to check-out. We really appreciated the thoughtful touches and how well-equipped the place was. Highly recommend for anyone looking for a cozy and roomy place to stay with friends!

Luxe

An elegant outdoor terrace is featured, showcasing a private pool with clear water surrounded by sun loungers. Comfortable seating areas are positioned nearby, offering panoramic views of the sea and the landscape. Lush greenery adds a touch of nature to the modern space.

Place to stay in Pyrgos Kallistis

4.93 out of 5 average rating, 14 reviews

Kamini White 1 Br

NathanRating, 5 stars1 day ago

Absolutely faultless, their is not one bad thing I can say about my stay it was absolutely perfect, team was fantastic and a great help, even better than the pictures views are breathtaking, if your thinking about staying here do it, it does not disappoint, airport transfers included and car rental, service is next to none

Guesthouse in Monolithos

4.75 out of 5 average rating, 252 reviews

By the sea

MarieRating, 5 stars1 week ago

I had a great stay. George was so attentive, friendly and helpful. Thank you so much for a lovely time.

Top guest favorite

A clear blue sky stretches overhead, complementing the vibrant turquoise of the swimming pool. Lounge chairs are lined along the pool deck, offering unobstructed views of the sea and distant islands, creating a serene outdoor space for relaxation.

Hotel room in Santorini

4.89 out of 5 average rating, 205 reviews

Villa Ilias, Standard Single Pool Facing

LorraineRating, 5 stars1 week ago

Honestly one of the most amazing places we have ever stayed! Georgios was so helpful with anything we needed and the view was our favorite on the island. Really made our honey moon feel extra special. Would highly recommend!

Top guest favorite

A shaded balcony is presented, featuring comfortable seating arranged around a glass-topped table. The horizon showcases a vibrant sunset over the sea, blending warm hues of orange and pink. The setting creates a serene spot for relaxation and enjoying coastal views.

Cycladic home in Monolithos

5 out of 5 average rating, 5 reviews

Blue Eyes Beach Villas 2

MichelleRating, 5 stars1 week ago

My best friend and I are travelling through Greece for my 50th birthday. We only had a one night stay at this beautiful seaside apartment. We wanted to experience a different side of Santoríni, the sunrise did not disappoint. The view is amazing and we enjoyed walking the beach at night with very little people around. The host met us on check in and it was a quick simple process. We will highly recommend this place to our friends and family.

Guest favorite

A clear view of a heated jacuzzi pool is captured, with the shimmering water reflecting the sunny sky. In the backdrop, the Aegean Sea is visible along with the serene landscape of Vourvoulos, showcasing traditional white buildings and hills.

Cycladic home in Vourvoulos

5 out of 5 average rating, 31 reviews

Panthea Suite Santorini - Private pool

HaleyRating, 5 stars1 month ago

It’s a very beautiful Airbnb and the hosts do an incredible job of making sure you have everything you need and even supply you with extra stuff! It was a little too chilly to use the pool/tub outside but it still had a very beautiful view! The only thing is, it is a very steep hill to get up to the actual house and the driveway is very rocky so keep that in mind if you are renting a vehicle.

Top guest favorite

An outdoor terrace features a private infinity pool with a stunning sea view. Comfortable lounge seating is positioned beside a wooden table. Stone walls frame the space, and a wooden pergola casts shadows on the sunlit area, creating a relaxed and inviting ambiance.

Private room in Santorini

4.95 out of 5 average rating, 91 reviews

Junior Suite Infinity pool & sea view BRILLIANCE

AmandaRating, 5 stars4 weeks ago

Peaceful, private, and beautiful area to stay and still walkable to others areas on the island. Their host Eleni is incredible by providing friendly service and booked all our activities for us (catamaran cruise, massages, photo shoot, and taxi) with strong communication! Her help made our trip memorable and less stressful. Breakfast was delicious and appreciate all the staff to make our stay fantastic!

Guest favorite