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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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 ￥25,350
￥28,141 total
includes taxes & fees
Sep 1 - Sep 2
Tholaria Boutique Hotel
A cozy, well-lit room with a stone wall, a curved bench, a small table, and a staircase leading to an upper level.

2. 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 ￥13,726
￥15,407 total
includes taxes & fees
Sep 5 - Sep 6
Esperia Luxury Suites
A terrace with white walls and blue accents, overlooking a clear blue sea and a rocky coastline.

3. 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 ￥17,536
￥19,581 total
includes taxes & fees
Sep 13 - Sep 14
Ihthioessa Boutique Hotel
A breakfast setup with a pineapple, toast, and jam on a table by a seaside view.

4. 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 ￥23,765
￥26,404 total
includes taxes & fees
Sep 20 - Sep 21
Aegean Sea Villas
A rooftop terrace with a hot tub, lounge area, and a view of a hilltop cityscape at night.

5. 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 ￥25,012
￥27,770 total
includes taxes & fees
Sep 17 - Sep 18
Melograno Villas
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.

6. 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 ￥28,976
￥32,670 total
includes taxes & fees
Sep 5 - Sep 6
Fildisi Hotel
A balcony with a white sofa, two round wooden tables, and a wicker basket.

7. Remezzo Suites

Remezzo Suites
Astypalaia
10.0 out of 10, Exceptional, (2 reviews)
"Owners are helpful and highly hospitable and location is convent for relaxing holiday by the beach. We are so lucky to have found this place for our vacation !!! "
Japan
Anonymous traveler
The price is ￥23,571
￥26,192 total
includes taxes & fees
Sep 12 - Sep 13
Remezzo Suites
An open yellow door leading to a table set with a tablecloth, chairs, and a vase of flowers, overlooking a scenic view of the sea and hills.

8. Kalderimi

Kalderimi
3.0 star property
Astypalaia
9.6 out of 10, Exceptional, (7 reviews)
"Un'oasi di bellezza. La struttura è ben curata e gestita; i proprietari sono discreti e disponibili. Le camere con vista mare strepitosa affacciano sulla baia di Livadi; ben distanziate tra loro offrono la giusta privacy; l'arredamento di gusto raffinato rispetta la tradizione del luogo. La colazione si potrebbe migliorare ampliando l'offerta delle portate "
Italy
angela
Kalderimi
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.

9. 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 ￥26,061
￥28,919 total
includes taxes & fees
Sep 18 - Sep 19
Aphrodite Luxury Apartment
A hotel room with a bed, a bedside table, a mirror, and a painting on the wall.

10. Apartment 'Stampalia Luxury No 1' with Sea View, Wi-Fi and Air Conditioning

Apartment 'Stampalia Luxury No 1' with Sea View, Wi-Fi and Air Conditioning
Astypalaia Town
The price is ￥13,922
￥14,293 total
includes taxes & fees
Sep 21 - Sep 22
Apartment 'Stampalia Luxury No 1' with Sea View, Wi-Fi and Air Conditioning
A bedroom with a bed, a dresser, a mirror, and a television.

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

Apartment 'For Two' with Balcony and Wi-Fi
Astypalaia
The price is ￥23,203
￥23,574 total
includes taxes & fees
Sep 1 - Sep 2
Apartment 'For Two' with Balcony and Wi-Fi
A modern outdoor pool area with a view of a distant island and sea.

12. Siesta Villas, Cycladic Elegance With Castle View

Siesta Villas, Cycladic Elegance With Castle View
Astypalaia
The price is ￥44,692
￥49,329 total
includes taxes & fees
Sep 4 - Sep 5
Siesta Villas, Cycladic Elegance With Castle View
A seaside hotel with a pool, lounge chairs, and a view of the sea.

13. 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 ￥45,478
￥45,849 total
includes taxes & fees
Sep 16 - Sep 17
Apartment 'Split Level with Sea View' with Sea View, Wi-Fi and Air Conditioning
A rooftop pool with a view of a lake and a hill.

14. Siesta Villas, Cycladic Elegance with Castle View

Siesta Villas, Cycladic Elegance with Castle View
Livadi
The price is ￥49,882
￥49,882 total
includes taxes & fees
Sep 14 - Sep 15
Siesta Villas, Cycladic Elegance with Castle View
A view through a window of a coastal town with buildings, a fan, and a clear sky.

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

Holiday Home 'Karai Traditional House' with Shared Terrace and Balcony
Astypalea
The price is ￥61,120
￥65,649 total
includes taxes & fees
Aug 26 - Aug 27
Holiday Home 'Karai Traditional House' with Shared Terrace and Balcony
A coastal town with white buildings, a prominent stone tower, and a clear blue sky.

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

Apartment 'For Seven' with Balcony and Wi-Fi
Astypalaia
The price is ￥54,759
￥55,130 total
includes taxes & fees
Sep 2 - Sep 3
Apartment 'For Seven' 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

Kallichoron Art Hotel

Kallichoron Art Hotel

10/10 Excellent
"Lovely, spotless clean room with amazing view of Chora. The staff was super nice and friendly and the breakfast which was served at our room was delicious. Thanks for everything!"
Eleni 7-night trip
Posted 6 days ago
Kallichoron Art Hotel

Find out more about Astypalaia

Search for holiday rentals in Astypalaia on Expedia! You can easily find your home rentals, villas, holiday apartments in Astypalaia using one of the methods below:

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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?

Renovated traditional house: This Astypalaia vacation home rental offers a fireplace, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. Make the most of the books in this rental home to help you unwind. Another good choice for your trip to Astypalaia is Siesta Villas, Cycladic Elegance with Castle View.

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.