A coastal town with white buildings, a harbor, and a hill with a castle.

Astypalaia Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Astypalaia vacation rentals

A pool area with a view of the sea, white furniture, and a small table with flowers.

1. Tholaria Boutique Hotel

Tholaria Boutique Hotel
2.0 star property
Astypalaia
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful property just a short walk up to the windmills. The host was amazing (so nice) and she knew everything about the island. Breakfast was great, the pool was a luxury and they also operated day trips to Koutsomitis & Kounoupes islands, a must do if you get the chance. We really enjoyed our stay."
Australia
Angelo
The price is CA $163
CA $181 total
includes taxes & fees
Oct 5 - Oct 6
Tholaria Boutique Hotel
A terrace with white walls and blue accents, overlooking a clear blue sea and a rocky coastline.

2. Ihthioessa Boutique Hotel

Ihthioessa Boutique Hotel
2.0 star property
Astypalaia
9.8 out of 10, Exceptional, (14 reviews)
"Nice & polite staff. Good breakfast and clean rooms"
United Kingdom
Panagiotis
The price is CA $124
CA $139 total
includes taxes & fees
Oct 16 - Oct 17
Ihthioessa Boutique Hotel
A serene waterfront view with a clear sky, a calm body of water reflecting the sun, and a modern building with a pool and seating area.

3. Fildisi Hotel

Fildisi Hotel
3.0 star property
Astypalaia
10.0 out of 10, Exceptional, (8 reviews)
"Ilias Helen and the staff where wonderful "
Australia
Jim
The price is CA $252
CA $284 total
includes taxes & fees
Sep 30 - Oct 1
Fildisi Hotel
A rooftop terrace with a hot tub, lounge area, and a view of a hilltop cityscape at night.

4. Melograno Villas

Melograno Villas
Astypalaia
10.0 out of 10, Exceptional, (8 reviews)
"The owner take care of guests in an amazing way,Vassliki is a super kind manager that is helpful for all you need."
United States
Luca
The price is CA $185
CA $206 total
includes taxes & fees
Oct 9 - Oct 10
Melograno Villas
A breakfast setup with a pineapple, toast, and jam on a table by a seaside view.

5. Aegean Sea Villas

Aegean Sea Villas
Astypalaia
10.0 out of 10, Exceptional, (3 reviews)
"Accommodation lovely and the guys kept our rooms so clean - new towels every day and a few essentials in the fridge ( water / milk / butter ) , lovely toiletries in the bathrooms . Astypalaia we loved - albeit pretty windy on most days we were there . "
United Kingdom
Janet
The price is CA $192
CA $213 total
includes taxes & fees
Sep 30 - Oct 1
Aegean Sea Villas
A modern bedroom with a curved bed, hanging light fixtures, and a view of a coastal town.

6. Provenzo Luxury Apartments & Suites

Provenzo Luxury Apartments & Suites
Astypalaia
8.0 out of 10, Very good, (1 review)
"Für den Check-In gibt es keine Rezeption. Hier am Besten im Vorfeld alles klären. Oder man fragt die Nachbarn. Aber ansonsten hat alles gepasst. Das Zimmer war sehr sauber und auch sehr schön eingerichtet und alles da, was es braucht."
Germany
Tanja
The price is CA $137
CA $154 total
includes taxes & fees
Sep 30 - Oct 1
Provenzo Luxury Apartments & Suites
A modern, minimalist interior with a curved seating area, a small table with a cup and glasses, and a visible doorway leading to a bedroom with a bed and a mirror.

7. Aphrodite Luxury Apartment

Aphrodite Luxury Apartment
Astypalaia
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful apartment right in the port, lovely views and close to restaurants and cafes. The manager, Ilias, is extremely helpful, professional, polite. Highly recommend this place. "
United States
Elizabeth
The price is CA $210
CA $233 total
includes taxes & fees
Oct 9 - Oct 10
Aphrodite Luxury Apartment
A cozy, well-lit room with a stone wall, a curved bench, a small table, and a staircase leading to an upper level.

8. Esperia Luxury Suites

Esperia Luxury Suites
Astypalaia
8.8 out of 10, Excellent, (3 reviews)
"Beautiful and quiet space! Definitely recommend. "
Canada
Pénélope
The price is CA $90
CA $102 total
includes taxes & fees
Sep 30 - Oct 1
Esperia Luxury Suites
A coastal view with a staircase leading to a building with white walls and blue accents.

9. Medieval Memory House

Medieval Memory House
Astypalaia
The price is CA $397
CA $438 total
includes taxes & fees
Oct 23 - Oct 24
Medieval Memory House
A rooftop pool with a view of a lake and a hill.

10. Siesta Villas, Cycladic Elegance with Castle View

Siesta Villas, Cycladic Elegance with Castle View
Livadi
10.0 out of 10, Exceptional, (1 review)
"Beautiful space with stunning views, great plunge pool and easy access to the beach. Hosts Popi and Antonio were fantastically kind, collecting us from the ferry, looking after our luggage on the last day and then delivering it to the port. They also delivered fresh pastries every day. Really enjoyed our time on Astypalea."
United States
Steve C.
The price is CA $274
CA $274 total
includes taxes & fees
Oct 1 - Oct 2
Siesta Villas, Cycladic Elegance with Castle View
A view through a window of a coastal town with buildings, a fan, and a clear sky.

11. Holiday Home 'Karai Traditional House' with Shared Terrace and Balcony

Holiday Home 'Karai Traditional House' with Shared Terrace and Balcony
Astypalea
The price is CA $354
CA $393 total
includes taxes & fees
Sep 30 - Oct 1
Holiday Home 'Karai Traditional House' with Shared Terrace and Balcony
A seaside hotel with a pool, lounge chairs, and a view of the sea.

12. Apartment 'Split Level with Sea View' with Sea View, Wi-Fi and Air Conditioning

Apartment 'Split Level with Sea View' with Sea View, Wi-Fi and Air Conditioning
Astypalaia Town
The price is CA $395
CA $398 total
includes taxes & fees
Sep 30 - Oct 1
Apartment 'Split Level with Sea View' with Sea View, Wi-Fi and Air Conditioning
A modern outdoor pool area with a view of a distant island and sea.

13. Siesta Villas, Cycladic Elegance With Castle View

Siesta Villas, Cycladic Elegance With Castle View
Astypalaia
The price is CA $218
CA $242 total
includes taxes & fees
Oct 11 - Oct 12
Siesta Villas, Cycladic Elegance With Castle View
A coastal town with white buildings, a prominent stone tower, and a clear blue sky.

14. Apartment 'For Seven' with Balcony and Wi-Fi

Apartment 'For Seven' with Balcony and Wi-Fi
Astypalaia
The price is CA $338
CA $342 total
includes taxes & fees
Oct 1 - Oct 2
Apartment 'For Seven' with Balcony and Wi-Fi
A bedroom with a bed, a dresser, a mirror, and a television.

15. Apartment 'For Two' with Balcony and Wi-Fi

Apartment 'For Two' with Balcony and Wi-Fi
Astypalaia
The price is CA $150
CA $153 total
includes taxes & fees
Oct 1 - Oct 2
Apartment 'For Two' with Balcony and Wi-Fi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Astypalaia Hotel Reviews

Castellano Village

Castellano Village

10/10 Excellent
"I cannot praise the Castellano enough. Built in a Cycladic style, rooms are fresh, exceptionally clean and have all you need. Each room has a terrace or balcony, with pool views. Located 15 minute drive to Chora, directly under flight path (though with only 1-2 small planes a day, this has no effect, it is quiet and peaceful in its setting with lovely pool area and plenty of parking. Extremely comfortbale beds, with branded toiletries provided and replenished. Kitchenette has fridge, microwave, hob and kettle (nearest mini market is 5 min drive away). Excellent air conditioning, which was not too noisy as some can be. Where the Castellano truly shines and deserves 7 stars is its owners and staff. Right from walking in, Nikos and family were welcoming, friendly and always on hand. They genuinely wanted you to enjoy your stay and offer recommendations and help. Would absolutely recommend to anyone staying in Astypalaia - one of the best stays we've had in Greece."
Matthew 5-night trip
Posted 12 days ago
Castellano Village

Find out more about Astypalaia

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Astypalaia. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Astypalaia?

Yes, we offer vacation rentals near top points of interest in Astypalaia, or you can select a more secluded option if you're looking for relaxation. Astypalaia is known for its waterfront and monuments. Make sure you have time to check out the gardens while you're in the area.

What are some of the best vacation home rentals that Astypalaia has to offer?

Apartment 'For Seven' with Balcony and Wi-Fi: This Astypalaia vacation home rental is equipped with a balcony, WiFi, and cable TV to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Some other homes for rent in Astypalaia include Siesta Villas, Cycladic Elegance with Castle View and Renovated traditional house.

How many vacation rentals are there in Astypalaia?

Expedia has 21 vacation rentals for your stay in Astypalaia.

What can I see and do in Astypalaia?

Astipaleas Beach and Livadi Beach are a couple of lovely local spots to get outside and enjoy nature. Astypalea Windmills and Astypalaia Castle are other places to visit while you're in town.

What are vacation rentals like in Astypalaia?

Vacation rentals are privately owned accommodations you can stay in for a few days or a quick weekend in Astypalaia. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips.