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

Astypalaia Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Astypalaia holiday rentals

A terrace with white walls and blue accents, overlooking a clear blue sea and a rocky coastline.

1. 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 NZ$181
includes taxes & fees
16 Oct - 17 Oct
Ihthioessa Boutique Hotel
A pool area with a view of the sea, white furniture, and a small table with flowers.

2. 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 NZ$252
includes taxes & fees
19 Oct - 20 Oct
Tholaria Boutique Hotel
A rooftop terrace with a hot tub, lounge area, and a view of a hilltop cityscape at night.

3. 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 NZ$235
includes taxes & fees
25 Oct - 26 Oct
Melograno Villas
A cozy, well-lit room with a stone wall, a curved bench, a small table, and a staircase leading to an upper level.

4. 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 NZ$140
includes taxes & fees
13 Oct - 14 Oct
Esperia Luxury Suites
A bedroom with a bed, a dresser, a mirror, and a television.

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

Apartment 'For Two' with Balcony and Wi-Fi
Astypalaia
Apartment 'For Two' with Balcony and Wi-Fi
A modern outdoor pool area with a view of a distant island and sea.

6. Siesta Villas, Cycladic Elegance With Castle View

Siesta Villas, Cycladic Elegance With Castle View
Astypalaia
The price is NZ$307
includes taxes & fees
14 Oct - 15 Oct
Siesta Villas, Cycladic Elegance With Castle View
A view through a window of a coastal town with buildings, a fan, and a clear sky.

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

Holiday Home 'Karai Traditional House' with Shared Terrace and Balcony
Astypalea
The price is NZ$371
includes taxes & fees
12 Oct - 13 Oct
Holiday Home 'Karai Traditional House' with Shared Terrace and Balcony
A rooftop pool with a view of a lake and a hill.

8. 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 NZ$344
includes taxes & fees
12 Oct - 13 Oct
Siesta Villas, Cycladic Elegance with Castle View
A coastal view with a staircase leading to a building with white walls and blue accents.

9. Medieval Memory House

Medieval Memory House
Astypalaia
Medieval Memory House
A coastal town with white buildings, a prominent stone tower, and a clear blue sky.

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

Apartment 'For Seven' with Balcony and Wi-Fi
Astypalaia
The price is NZ$297
includes taxes & fees
1 Nov - 2 Nov
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

Caldera Studios

Caldera Studios

8/10 Good
"We had an amazing view from our balcony. Apartments are in excellent location - just a short walk to Pera Gialos port/bus stop, and in the other direction to a good supermarket. Owner was kind, giving us a gift when we left, and also a bottle of red wine as well as a bottle of water, when we arrived. The complimentary toiletries were also good. Our room was cleaned regularly by helpful and kind staff, but there was a slight musty smell inside the wardrobe - possibly just the smell of the wood used, as our room was really well ventilated. Plenty of hangers in the wardrobe, and adequate kitchenware. Note that listed 'Amenities' on Expedia website incl. 'safe at front desk' but there is no front desk or reception area; 'laundry facilities' also listed which doesn't apply to all rooms, and there is absolutely no restaurant/snack bar (or breakfast) offered on site... you must drive for 10 minutes up to Chora and then down to Livadi beach, or walk for 35 mins, to use the owner's taverna (but there are plenty of other nearby tavernas of course!). Sadly, the pool was not really usable for me - I prefer not to be completely out of my depth, so at 1.7m/1.8m it was too deep for me. Also, the area around the pool could do with some maintenance work/tidying up, especially if using the steps to the side of the accommodation to go down to the pool. Finally, wi-fi wasn't consistent - only really works with reliability on the balcony. However, we did really enjoy our stay here."
Tessa 10-night trip
Posted 5 days ago
Caldera Studios

Find out more about Astypalaia

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Astypalaia holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Astypalaia. 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 Astypalaia. 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 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 holiday 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 Astypalaia short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Astypalaia?

Yes, there are holiday rentals close to the most popular sights in Astypalaia, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Astypalaia has to offer?

Apartment 'For Seven' with Balcony and Wi-Fi: This highly rated holiday home rental in Astypalaia 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 that 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 holiday rentals are there in Astypalaia?

Expedia has 21 holiday 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 holiday rentals like in Astypalaia?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Astypalaia. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family trip.