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Vacation rentals in Sikinos

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Top-rated vacation rentals in Sikinos

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Cycladic home in Koumpara
5.0 out of 5 average rating, 3 reviews

Ios Sea view apartment with pool 2B

Kick back and relax in this stylish space in Ios that has beautiful, panoramic sea, sunset view and a small swimming pool (sun heated only) It is only 5 minutes walking to Koubara beach or the famous Pathos club A 60 sq meters apt built in 2026 that has 1 Queen bed, 1 single bed, living room with sofa bed, kitchenette with espresso machine / sandwich maker Large Patio with pool (operates May to October) Shared Parking available within the complex of 4 suites Port , Ios town, shops are 3 km away

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Guest favorite
An inviting heated cave swimming pool features smooth white walls and bright blue water, with a metallic ladder providing access. Natural light filters through the archway above, creating a serene atmosphere within the private space.
Cycladic home in Oia
4.89 out of 5 average rating, 64 reviews

Exclusive Villa with Outdoor Heated Pool

The villa is exquisitely located in the scenic village of Oia!! The interior fine art design of this superb cave two bedroom Pool Villa includes the ultimate value of space, flirting with the lights and shadows of ancient Greece. Dive into your own large heated outdoor cave swimming pool with hydro-massage and excite your senses. Walk into your balcony for enjoying the breathtaking views of Caldera, Aegean sea and unparalleled Santorini direct sunset. Discover the uniqueness of Santorini, Oia!!!

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Top guest favorite
A private heated pool is seen on a terrace, offering unobstructed views of the deep blue sea and distant islands. The scene includes iconic white buildings with blue domes, set against a clear sky, showcasing typical Santorini architecture.
Cycladic home in Oia
4.95 out of 5 average rating, 415 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

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Top guest favorite
A private terrace features wooden railings and stone seating, overlooking the expansive sea and rugged cliffside landscape. The distance reveals a striking white structure atop the mountain, while the sky is filled with soft clouds and bright sunlight.
Cycladic home in Folegandros
4.99 out of 5 average rating, 79 reviews

Alosanthos Private Residence

Inside the medieval Kastro | The Alosanthos residence is built in the heart of the medieval settlement of the Chora, both at the center of the Folegandros Kastro (lit. castle) and uniquely situated on its steepest section With breathtaking views, the private residence Alosanthos is located in the heart of the Castle, the medieval settlement of Chora. It enjoys the privilege of a quiet neighborhood, while the picturesque center is within walking distance. Ideal for couples and families.

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Guest favorite
A spacious bedroom features a double bed with neutral bedding, accented by striped pillows. Wall decorations include woven sun-shaped pieces. Soft lighting is provided by pendant lamps on either side of the bed. An ensuite bathroom is visible through an open doorway.
Cycladic home in Chora
5.0 out of 5 average rating, 21 reviews

Cycladic Sand The House

Located in the heart of Ios Town, in a central yet quiet, picturesque alley, this house stands out for its atmospheric design and elegant Cycladic aesthetics. Its white arches, courtyard overlooking the blue-and-white bell tower, natural materials, and modern touches create a unique accommodation experience. Perfect for couples, families and groups of people who love authenticity. The ultimate tranquility combined with the unique energy of Ios offer you moments of true vacation bliss.

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Superhost
A tranquil patio area features a wooden bench adorned with light blue and white cushions. A small table rests nearby, accompanied by a white cup, overlooking the expansive blue ocean and clear blue sky.
Cycladic home in Agios Georgios
4.7 out of 5 average rating, 43 reviews

La Casita- Folegandros, Greece

Situated on the most beautiful island in Greece- Folegandros. Within the small island directly on Agios Georgios beach lies La Casita one of the numbered places directly on the ocean. Quiet, secluded, and implausibly serene. La Casita has two beds with a bathroom, it has a kitchenette. Outside it has its own patio with a spectacular view of the ocean. 100% Solar Power. We sell out in summer please don’t message to negotiate pricing. GREY/BEACH HOUSE BOOKED SEPARATELY SEE BELOW

ValueLocationSleep quality

Top guest favorite
A heated mini pool is situated within a cave-style space, illuminated by soft light from surrounding fixtures. An archway frames a view of the sea, with calming turquoise water reflecting the gentle lighting, creating a relaxing environment.
Cycladic home in Fira
4.99 out of 5 average rating, 114 reviews

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.

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Top guest favorite
A serene outdoor terrace features a stone table set for two, accompanied by comfortable seating. Candles provide a soft glow at dusk, with a view of a cliffside village and the deep blue Aegean Sea in the background. The evening sky transitions to a twilight hue.
Castle in Municipality of Folegandros
4.95 out of 5 average rating, 114 reviews

Folegandros-Cliffhouse

Where History Meets the Edge of the Aegean Perched on the dramatic cliffs of Castro, this unique 800-year-old Venetian house offers breathtaking Aegean views from two magical sea-view verandas. Part of the original Venetian Castle in Chora, it combines centuries of history with an extraordinary cliffside setting. Located in the heart of the village yet wonderfully peaceful, the car-free Castro offers a rare blend of authenticity, tranquility, and unforgettable island charm.

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Top guest favorite
A private terrace features comfortable seating with plush cushions, small wooden table, and decorative bottles. The space provides a clear view of the deep blue ocean and surrounding caldera, complemented by the whitewashed buildings of Oia in the background and a bright blue sky.
Guest suite in Oia
4.99 out of 5 average rating, 235 reviews

Suite with 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. Right out of a post card between the two iconic blue domes of Oia. This suite has a private terrace with astonishing panoramic view to the caldera and the blue domes. Santorini International Airport is about 17 km from Oia Spirit, and the Ferry Port at approximately 23 km.

LocationFamilyLaundry

Top guest favorite
A tranquil outdoor jacuzzi is visible, with a view of iconic blue-domed structures nearby. The sun casts a warm glow, reflecting on the water. The serene ambiance is enhanced by the surrounding landscape, suggesting a peaceful retreat in a picturesque setting.
Cycladic home in Oia
4.99 out of 5 average rating, 179 reviews

Santo Blue Horizon Villa | Jacuzzi | Caldera View

This unique villa is located in the heart of Oia in an excellent position and has stunning views. The famous Three Domes just in front of villa with panoramic view overlooking the santorinian caldera and the aegean sea, have magnetized visitors and photographers from all over the world, making it, the most popular spot in Santorini. The villa is in perfect harmony with the natural surroundings of the area and follows the principles of traditional Cycladic architecture.

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Guest favorite
An outdoor seating area is highlighted by a coffee table surrounded by soft, white lounge chairs. A private jacuzzi can be seen in the background, with a stunning view of the blue ocean and distant islands. A pergola provides shade, enhancing the relaxing atmosphere.
Dome in Santorini
4.92 out of 5 average rating, 314 reviews

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.

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Top guest favorite
A private indoor cave pool is set within a smooth, naturally formed alcove, with gentle lighting reflecting off the water’s surface. A staircase is visible in the background, leading to a brightly lit area, enhancing the cave's unique ambiance.
Place to stay in Vothonas
4.96 out of 5 average rating, 298 reviews

Mystagoge Retreat with subterranean pool/jacuzzi

Mystagoge Retreat is a unique traditional house, which can accommodate up to two people. A private heated indoor cave pool with jacuzzi will be waiting for you to offer a mystic experience. A light breakfast basket with rusks, jam, honey, tea coffee, milk and butter. Amenities included are WI-FI, air-conditioning, in all areas of house, free parking, sun filled traditional yard with sunbeds, dining area and shared BBQ.

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Popular amenities for Sikinos vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Sikinos

Top guest favorite
A wooden gate opens towards a serene beach scene, with turquoise waters stretching into the distance. The sandy shore is visible, framed by a gently sloping hillside. A clay figurine can be seen atop a wall, adding a subtle artistic touch to the view.
Cycladic home
4.97 out of 5 average rating, 91 reviews

Xenia's Beach House, Vathi, Sifnos

ValueFamilyWalkability

Top guest favorite
Cycladic home in Oia
5.0 out of 5 average rating, 56 reviews

Ether luxury suite with amazing heated jacuzzi

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Top guest favorite
Cycladic home in Mylopotas
5.0 out of 5 average rating, 27 reviews

Anemone III w/Private Pool — 5 minute from beach

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Guest favorite
Cycladic home in Vivlos
5.0 out of 5 average rating, 5 reviews

Villa THÉA I

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Top guest favorite
Home in Merovígli
5.0 out of 5 average rating, 22 reviews

Esmi Suites 4 Private Outdoor Jacuzzi Sunset View

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Guest favorite
A spacious outdoor terrace is presented with a rustic wooden table and two chairs. A built-in bench, adorned with colorful striped cushions, offers additional seating. The smooth surfaces and clean lines of the white walls create an inviting atmosphere for relaxation.
Home in Nisí Síkinos
4.96 out of 5 average rating, 24 reviews

Sikinos traditional house in Kastro

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A sunbed overlooks a coastal view, featuring calm waters and a scenic shoreline. White buildings dot the landscape, framed by gentle hills under a clear sky. A traditional clay pot is positioned beside the sunbed, adding to the terrace's welcoming feel.
Apartment in Alopronoia
4.92 out of 5 average rating, 25 reviews

SIKINOS, THE BEST VIEW AT THE 'PEARL OF CYCLADES'

LocationFamilyLayout

Guest favorite
A view of whitewashed buildings nestled against the rocky landscape, highlighting the traditional architecture of Sikinos. The foreground displays textured stone formations, while the serene blue waters reflect the nearby boats anchored at the shore.
Cycladic home in Alopronoia
5.0 out of 5 average rating, 27 reviews

Beautiful seaside Private Villa

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Frequently Asked Questions

  • What are the best places to stay in Sikinos?

    Stay in the charming Chora area, known for traditional architecture and narrow streets, or near the port for easy access to seaside views. Neighborhoods around the village squares are often recommended for their quiet atmosphere and proximity to local amenities.

  • What are the best things to do in Sikinos with kids?

    Kids often enjoy swimming at sandy beaches, exploring castle ruins, and hiking gentle paths with scenic views. Family-friendly workshops featuring local crafts and attending community cultural events are also frequently suggested.

  • What are some of the best things to do in Sikinos?

    Explore the historic hilltop village, visit ancient ruins, and relax on quiet beaches surrounded by clear waters. Hiking paths, local wineries, and the chance to join seasonal festivals are frequently suggested activities.

  • How is the weather in Sikinos?

    Sikinos usually has warm, dry summer days and mild winters, typical of Aegean island climates. Breezy evenings are common, so a light jacket can be useful for sunset walks or outdoor dining.

  • When is the best time to visit Sikinos?

    Late spring through early fall is often recommended for pleasant temperatures and lively cultural gatherings in Sikinos. Quiet periods in other months appeal to those seeking a more tranquil experience amid the island’s scenery.

  • What are the best places to visit in Sikinos?

    The Church of Panagia Pantanassa, the ancient Episkopi Monument, and the picturesque Chora village are frequently suggested for visitors interested in history or local culture. Beaches around the island also invite relaxing by the water.

  • What are some hiking trails in Sikinos?

    Hiking trails in Sikinos connect historic villages, terraced hillsides, and coastal viewpoints. Paths leading to Episkopi Monument or chapels around the island are often recommended for scenic walks.

  • What are some family activities we can do in Sikinos?

    Families can enjoy swimming at quiet beaches, hiking trail routes through scenic landscapes, and sampling local foods at village tavernas. Join cultural events or visit the historical monuments for engaging learning experiences together.

  • What are some of the best day trip ideas from Sikinos?

    Day trips from Sikinos often include exploring nearby islands with distinct Cycladic architecture or visiting traditional markets in surrounding towns. Coastal boat excursions and visits to local vineyards are popular ways to experience the region.

  • Are there any pet friendly accommodations available in Sikinos?

    Some accommodations in Sikinos may welcome guests traveling with pets, though availability can vary. It is helpful to check individual listing details or reach out to hosts directly to learn more about pet policies.

  • What are some local tips for visiting Sikinos?

    Wear comfortable shoes for navigating hilly villages, and bring a sun hat for open island trails. Locals suggest trying seasonal produce and joining cultural festivities for a deeper understanding of Sikinos traditions.

  • What is Sikinos known for?

    Sikinos is known for its tranquil atmosphere, historic villages, and ancient monuments. The island has scenic beaches, locally rooted traditions, and a strong agricultural heritage reflected in its cuisine and festivals.

  • What are the best hidden gems to explore in Sikinos?

    Explore secluded beaches along Sikinos’s coastline, discover small chapels tucked into the hills, and wander lesser-known trails connecting terraced fields. Local workshops and vineyards around the villages are also often recommended for an authentic experience.

  • What are the best foods to try in Sikinos?

    Sikinos has locally rooted flavors such as grilled fish, hearty stews, and fresh salads made with island-grown produce. Cheese pies, olive oil, and seasonal sweets are frequently suggested for those wanting a taste of regional cuisine.

  • What should I bring for a trip to Sikinos?

    Bring comfortable walking shoes for village steps and trails, a light jacket for cooler evenings, and a sun hat or sunscreen for protection. Swimwear and a reusable water bottle are also frequently recommended for outdoor activities.

  • What is the nightlife in Sikinos like?

    Nightlife in Sikinos is relaxed, with locally run tavernas and bars welcoming guests around village squares or near the waterfront. Summer evenings may feature music gatherings and neighborhood festivities, creating a friendly, sociable atmosphere.

  • What are the most popular events or festivals in Sikinos?

    Sikinos has traditional festivals in summer, where music, dance, and local foods are enjoyed by both residents and visitors. Religious celebrations and cultural gatherings often draw people to village squares around mid and late summer.

  • Are there family friendly vacation rentals in Sikinos?

    Many vacation rentals in Sikinos are family friendly, particularly those in Chora and around the port. Homes often have features suitable for groups and easy access to local amenities, beach areas, and village squares.