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Vacation rentals in Astypalaia

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Top-rated vacation rentals in Astypalaia

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Top guest favourite
A modern stone house is presented with a whitewashed exterior and gray shutters, complemented by a tree in the foreground. An entryway is visible, revealing a glimpse of the interior. The clear blue sky enhances the serene setting.
Cycladic homes in Astypalea
5 out of 5 average rating, 8 reviews

Karai the House Project

Enjoy an experience with style in the cosy modern stone house situated in Astypalaia Town, in a central and quieted location, within the Castle alleys. The property features quiet street views and a private entrance, has a balcony with awesome sea view, a bedroom with double bed, a living room, bathroom and a well equipped kitchen. It is 300 m from Church of Panagia Portaitissa and 500 m from Gouerini Castle. Free WiFi is available throughout the property and Pera Gialos Beach is 500 m away.

Top guest favourite
An outdoor space features a private pool surrounded by a spacious terrace with a stone pattern. Comfortable seating is arranged under a shaded area, offering views of the sea and a distant town. Lush greenery complements the tranquil setting.
Villa in Tzanaki Astypalaia
5 out of 5 average rating, 14 reviews

Siesta Villas nearby Tzanaki Beach

Kick back and relax in this calm, stylish space.Just 150 metres from crystal clear water of Tzanaki Beach and only 2 minutes by car from the Cosmopolitan beach of Livadi which boasts local taverns, cafes, beach bars and mini markets Set in the middle of lush vegetation with a fabulous view of the sea and castle. Leave your worries behind while you enjoy the peace and serenity of the tranquil surroundings. Only a 7 minute drive away from Chora and the Old Town. Free parking provided.

Guest favourite
A bright studio space features a double bed with a simple white headboard and colorful pillows. A mirror-fronted wardrobe enhances the room's openness. A small bedside lamp provides soft lighting, while a desk with a notepad and reading glasses sits nearby.
Apartment in GR
4.97 out of 5 average rating, 37 reviews

Deluxe Studio @ Vithos Aparthotel

Τα Deluxe Studios είναι κομψά, πλήρως επιπλωμένα στούντιο που βρίσκονται στο ισόγειο του συγκροτήματος. Διαθέτουν ένα διπλό κρεβάτι, γραφείο και ντουλάπα με ολόσωμο καθρέπτη, πλήρως εξοπλισμένο κουζινάκι με ψυγείο, πάγκο φαγητού και σκαμπό, και ένα πολυτελές μπάνιο με ντουζιέρα. Προσφέρουν απευθείας πρόσβαση στον προαύλιο χώρο που βρίσκεται στα όρια της παραλίας του Πέρα Γυαλού, με μοναδική θέα προς τη Χώρα και το Ενετικό κάστρο.

Guest favourite
The sleeping area features a spacious bed adorned with crisp white linens and a neutral-colored decorative pillow. Above the bed, three abstract wooden wall art pieces in earthy tones are complemented by two woven pendant lights, creating a calming ambiance.
Cycladic homes in Livadia
5 out of 5 average rating, 8 reviews

Silia II

The residence ASiLIA II is located in Livadi, a seaside settlement of Astypalaia. It is a quiet choice of Cycladic style accommodation with modern decorative elements. It is just 2 km from the island's Chora and 60 meters from the cosmopolitan beach of Livadi. The visitor has a wide choice of traditional taverns, ouzeries and cafes which are literally on the edge of the wave overlooking the town and the enchanting castle.

Superhost
A charming outdoor patio area features a large umbrella providing shade over a small dining table and two chairs. Decorative plants and greenery surround the space, with a staircase leading to the entrance of the house. Blue accents add a pop of color against the stone walls.
Cycladic homes in Astypalea
4.84 out of 5 average rating, 62 reviews

Cozy traditional House in Hora Astypalaia

Fully restored, cozy traditional house in the heart of Astypalaia's main village, Hora. Has one double, one single beds and a large couch that becomes a single bed. The house has its own patio as well as a rooftop balcony with a view at the Venetian castle and the Aegean sea. Our house is ideal for families or groups up to four people

Top guest favourite
A spacious sleeping area is presented with a wooden bed and a cozy seating arrangement. Light walls are contrasted by a textured accent piece. A large overhead skylight allows natural light to brighten the room. Minimalist furnishings are arranged for comfort and practicality.
Cycladic homes in Astypalea
5 out of 5 average rating, 17 reviews

Katoi luxury suite

Centrally located in the heart of Astypalaia, 'Katoi' is a minute's walk from the island's main square and the scenic windmills. Due to its convenient location it offers quick and easy access to restaurants, cafes, shopping and popular nightlife. 'Pera gialos' the central pebble beach of the town is less than 5' walk away as well.

Guest favourite
A comfortable seating area is presented with neutral-colored cushions and two small black tables beside it. In the background, a spacious bed is prepared with fresh towels, while decorative wall art adds subtle texture to the white walls.
Apartment in Astypalea
4.96 out of 5 average rating, 27 reviews

White Studio

Comfortable studio with equipped kitchen, bathroom and private balcony. Ideal for couples or two friends who want to spend their holidays in the enchanting Astypalaia. It is just 300m from Chora and a 10-minute walk from the port. Finally, within walking distance there are supermarkets, banks, a pharmacy, cafes and a bakery.

Top guest favourite
Home in Astypalaia Island
5 out of 5 average rating, 29 reviews

InHarmony | at city heart @ vivere luxury suites

Designed and decorated for the modern traveler who seeks comfort and style in the welcoming atmosphere of an apartment and at the same time the comforts of a quality hotel, InHarmony's hospitality area has it all. Staying at InHarmony means easy access to the best of what Chora and Pera Gialos have to offer.

Guest favourite
A charming outdoor area is framed by vibrant pink bougainvillea, offering a cozy seating arrangement with a small table and wooden chairs. A traditional clay pot and potted plants are arranged nearby, contributing to a serene atmosphere surrounded by lush greenery.
Apartment in Astypalea
4.87 out of 5 average rating, 38 reviews

Beautiful House in Chora of Astypalea

A two-space traditional house with garden and beautiful view to the sea and the amazing castle of Astypalaia. The house has a bedroom with one (1) build in double bed and a living room with two (2) build in sofa, It also has a dining area and a kitchen, one bathroom and a very beautiful garden.

Guest favourite
Apartment in Astypalea
5 out of 5 average rating, 30 reviews

Astypalaia Island, Punta Nera Resort - Room 4

Punta Nera Room 4 is located on the hill of Agioi Anargyroi, just 150 meters from the beach of Pera Gialos and 600 meters away from Chora. It has access to all the central points of the island! It overlooks the old harbor, the various Aegean isles, the mills and Chora with its castle.

Guest favourite
A bright living area is filled with natural light from large, open windows, featuring a white sofa adorned with soft cushions. A white table displays decorative shells and a straw hat, while a potted plant adds a touch of color to the space.
Apartment in Astypalea
4.91 out of 5 average rating, 53 reviews

Anemomilos studios

My place is close to the city center. Reasons you'll love my place: comfortable environment, the view, the location, high ceilings and kitchen. My place is good for couples, solo adventurers, business travelers, families (with kids), and pets.

Guest favourite
A panoramic view captures the cascading white buildings of Astypalea, nestled on the hillside. The castle is visible atop the hill, accompanied by a clear blue sky. A blue towel drapes over a ledge in the foreground, contrasting with the bright surroundings.
Cycladic homes in Astypalea
4.99 out of 5 average rating, 85 reviews

Studio-apartment with great view

One room with 2 beds, a small kitchen and a toilet. It is located at the old port of Astypalea, Pera Gialos. From the balcony one can gaze at the magnificent view of the castle and the sea.

Popular amenities for Astypalaia vacation rentals

When is the best time to visit Astypalaia?

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Frequently Asked Questions

  • What are the best places to stay in Astypalea?

    Chora is popular for its scenic castle views, while Livadi attracts those who enjoy beach proximity and gardens. Maltezana is often chosen for its quieter harbor setting and traditional village feel.

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

    Kids can explore sandy beaches, climb up to the island’s windmills, and enjoy local pastries in village bakeries. The castle in town is frequently suggested as a fun spot for families to discover together.

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

    Explore the Venetian castle, stroll through whitewashed lanes of Chora, and relax on quiet beaches. Many visitors enjoy boat tours, snorkeling, and local cultural evenings.

  • How is the weather in Astypalea?

    Astypalea has mild, rainy winters with temperatures around 47–63°F (9–17°C), and hot, dry summers often reaching 76–96°F (24–35°C). Summer is mostly sunny, while spring and autumn bring more comfortable temperatures for outdoor exploration.

  • When is the best time to visit Astypalea?

    Late spring to early autumn is often recommended for Astypalea, when temperatures are warm and outdoor festivals are frequent. Early summer is popular for milder weather and fewer crowds.

  • What are the best places to visit in Astypalea?

    Explore Chora for its windmills and castle, visit Livadi’s beaches, and wander the harbor of Maltezana. The Archaeological Museum and Agios Ioannis Monastery are also frequently suggested stops.

  • What are some hiking trails in Astypalea?

    Astypalea has several scenic walking paths, such as the route to Agios Ioannis Monastery, coastal trails near Chora, and hillside tracks around Livadi. These trails often feature sea views, local flora, and opportunities for quiet nature exploration.

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

    Families often explore sheltered beaches for swimming or sandcastles, wander through the historic castle, and visit small museums in town. Guided boat excursions and gentle walking paths are frequently suggested for discovering coastal scenery together.

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

    Travelers frequently join boat tours around nearby islets, visit hidden beaches, or explore local farms and monasteries. Some opt for traditional fishing experiences or snorkeling excursions in turquoise coves.

  • Are there any pet friendly accommodations available in Astypalea?

    Astypalea has pet-friendly accommodation options, especially in villages like Livadi and Chora. A variety of stays are available where pets are welcomed with advance notice.

  • What are some local tips for visiting Astypalea?

    Try local cheese pies, carry cash for small shops, and wear comfortable shoes for exploring hilly villages. Joining a traditional feast or sailing tour is a favorite way to connect with Astypalea’s community.

  • What is Astypalea known for?

    Astypalea is known for its iconic butterfly shape, hilltop castle, and windmills in traditional villages. The island also has crystal-clear waters and a tranquil, Cycladic atmosphere with Dodecanese influences.

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

    Many enjoy seeking out early Christian basilica remains at Agios Vasilios, quiet pebble coves, and traditional bakeries tucked in side streets. Wandering lesser-known villages around the island is also often recommended for those drawn to local culture.

  • What are the best foods to try in Astypalea?

    Astypalea has local specialties like saffron-tinged cheese pies, fresh fish, and thyme honey. Many travelers enjoy homemade pastas, goat dishes, and spoon sweets featuring local fruit.

  • What should I bring for a trip to Astypalea?

    Pack lightweight clothing, sun protection, and comfortable shoes for exploring Astypalea’s villages and paths. Bringing swimwear, a sun hat, and layers for cooler evenings is frequently suggested.

  • What is the nightlife in Astypalea like?

    Astypalea has a relaxed nightlife scene, centered around cozy bars, cafe terraces, and a few lively beach spots that stay open late. Many visitors enjoy unwinding in Chora with music, local drinks, and sunset views.

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

    Astypalea often celebrates religious festivals during summer, including local feasts with dancing and music. Cultural events, such as traditional music nights and open-air performances, are frequently suggested around village squares or historical sites.

  • Are there family friendly vacation rentals in Astypalea?

    Many vacation rentals in Astypalea welcome families, especially in Livadi and the central parts of Chora. Larger homes, apartments, and sea-view properties are often suggested for family stays.

Quick stats about vacation rentals in Astypalaia

  • Total vacation rentals

    Explore 140 vacation rentals in Astypalaia

  • Nightly prices starting at

    Astypalaia vacation rentals start at $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,610 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    130 of Astypalaia vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Astypalaia rentals

  • 4.9 Average rating

    Astypalaia stays are highly rated by guests—averaging 4.9 out of 5!

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