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Holiday rentals in Sikinos

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Top-rated holiday rentals in Sikinos

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

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Top guest favourite
A spacious rooftop terrace features a heated Jacuzzi surrounded by sunbeds. The stunning view showcases the Caldera and Aegean Sea at sunset, with colorful skies and the scenic cliffs of Fira in the background.
Cycladic home in Fira
4.99 out of 5 average rating, 143 reviews

Three bedroom Villa with two Caldera View Jacuzzi

This luxury villa has the best location and feature specious terraces with famous view of Caldera and Aegean sea .Roof top terrace have heated Jacuzzi and comfortable sun-lounges.There is outdoor furniture next to Jacuzzi where you can enjoy breakfast and dinner with unforgettable view . Daily breakfast and cleaning make your stay comfortable .Each bedroom have private bathroom . In a walking distance you will find restaurants,bars, museums and supermarkets.Food delivery available.Free wi-fi

Top guest favourite
A private terrace features a small jacuzzi with panoramic views of the sea. A sunbed with a cushion is positioned beside a small wooden table, inviting relaxation. Two simple chairs are placed nearby, enhancing the tranquil outdoor space against the clear blue sky.
Cycladic home in Imerovigli
5 out of 5 average rating, 141 reviews

Cave House with Private Heated Jacuzzi

Perched on the cliff-side nearly 400 meters above the sea. Ikia Kriton is tradition Cave House with Private Jacuzzi in Imerovigli village blessed with breathtaking views of Caldera and ideally placed to discover the whole island.Totally renovated in 2021 from an old town house,the elegant minimalist building fully embraced local architecture and traditional features whilst tastefully combining local handcrafted furniture with modern flourishes and offers abundant space to relax indoor-outdoor.

Top guest favourite
A heated plunge pool is featured within a uniquely shaped archway, with clear blue water reflecting the sun. A stunning view over the ocean and distant islands is visible through the opening. Decorative cushions and a small table with refreshments enhance the inviting atmosphere.
Villa in Imerovigli
4.99 out of 5 average rating, 168 reviews

Ventus Paradiso Villa, Outdoor Heated Plunge Pool

Our cave villa comes with sentimental value as it belonged to our grandmother. Dated back to 1920's brings a great heritage. The villa was totally renovated in 2015, transforming a traditional cave into a luxury residence following faithfully the unique cycladic architecture with exceptional modern esthetics. The villa consists of two bedrooms with ensuite bathrooms, a dining area and a small kitchenette. It features a heated plunge pool and an upper terrace with panoramic view over Caldera.

Guest favourite
A private plunge pool is visible in the foreground, reflecting clear blue water. The stunning caldera view features vibrant blue dome churches in the distance, with the Aegean Sea stretching out toward a clear sky. Whitewashed buildings create a serene backdrop.
Cycladic home in Oia
4.97 out of 5 average rating, 306 reviews

Santorini blue, caldera views, private pool

Traditional Santorini cave house with famous blue dome churches, postcard perfect caldera views in the heart of Oia. next to main path.. Private plunge heated pool with panoramic views. Next to Island blue, Serenity &Eternity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities Other villas : Island blue, Eternity,Serenity,Captains blue, Secret garden, Sailing &Sky blue Flexible on pandemic related cancellations!

Guest favourite
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, 109 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.

Guest favourite
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 Folegandros
4.94 out of 5 average rating, 109 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.

Top guest favourite
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, 222 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.

Top guest favourite
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, 172 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.

Guest favourite
A private patio features a soothing Jacuzzi with sunbeds for relaxation, overlooking the expansive sea and stunning Caldera views. A decorative bowl is placed on a small table beside the Jacuzzi, while soft hues of sunset create a calming ambiance in the background.
Home in Oia
4.96 out of 5 average rating, 146 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 favourite
Cave in Fira
4.87 out of 5 average rating, 319 reviews

Mirabo Two Bedroom Maisonette with Caldera View

Mirabo Villa’s homonymous suite built in maisonette style has two different leveled bedrooms with double beds making it ideal for families, group of friends and honeymooners who want to enjoy their holidays in a very comfortable and relaxing way. The two separate and spacious bathrooms are beautifully styled and the living room offers hours of relaxation . On the second floor, you can enjoy the caldera & volcano views and the sunset from the private balcony.

Top guest favourite
An infinity pool with crystal-clear water reflects the serene sky, framed by a curved architectural feature. The pool seamlessly blends into the view of the caldera and volcanic islands, providing a tranquil setting for relaxation.
Cycladic home in Akrotiri
5 out of 5 average rating, 224 reviews

Anemos suite -Private infinity pool & patio

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 favourite
Place to stay in Imerovigli
4.95 out of 5 average rating, 147 reviews

Esmi Suites 2 Private Outdoor Jacuzzi Sunset View

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.

Popular amenities for Sikinos holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Sikinos

Top guest favourite
The historic manor house features pink stone walls, providing a rustic charm. Two blue-framed windows can be seen on the upper level, while a staircase leads to the entrance. Surrounding hills and a clear sky suggest a serene landscape.
Home in Kourounochori
5 out of 5 average rating, 54 reviews

Kambones 1615 Ηistoric Venetian home

Guest favourite
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 Sikinos
4.95 out of 5 average rating, 21 reviews

Sikinos traditional house in Kastro

Top guest favourite
Cycladic home in Oia
5 out of 5 average rating, 43 reviews

Ether luxury suite with amazing heated jacuzzi

Guest favourite
An outdoor terrace features sun loungers arranged beside a small pool, framed by natural stone walls and lush greenery. A shaded area is provided by an overhanging roof, and decorative plants add a touch of color. The inviting space is designed for relaxation.
Cycladic home in Karavostasis
4.98 out of 5 average rating, 41 reviews

Maistros - Mikros Vorias Folegandros

Top guest favourite
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, 75 reviews

Alosanthos Private Residence

Guest favourite
A serene outdoor seating area is visible through a window, featuring two wooden chairs positioned toward the expansive sea view. The landscape is characterized by gentle hills leading down to the ocean, with distant islands visible on the horizon.
Cycladic home in Folegandros
4.91 out of 5 average rating, 32 reviews

Pétra (MYLOI Folegandros Studios)

A traditional whitewashed structure is showcased, featuring a spacious outdoor terrace supported by white wooden beams. The clear blue sky provides a bright backdrop, highlighting the simplicity of Cycladic architecture. Various plants are visible along the edges, contributing to the serene atmosphere.
Cycladic home in Fira
4.83 out of 5 average rating, 12 reviews

Sigalas house, Sikinos island

Top guest favourite
Cycladic home in Chora
5 out of 5 average rating, 42 reviews

Heliopetra Punta Ios - Katikia Kallitsi

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.

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