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

Hotels with Swimming Pool in Astypalaia, South Aegean

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Check availability on Astypalaia Hotels with Swimming Pool

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Astypalaia hotels with a pool

A pool area with a view of the sea, white furniture, and a small table with flowers.
A balcony with a view of the sea and hills.
A bedroom with a bed, a TV, a sofa, and a view of the sea.
A coastal view through a window with a view of the sea and rocky terrain.

1. Tholaria Boutique Hotel

Tholaria Boutique Hotel
Astypalaia
  • Sunshine bathes the Mediterranean aparthotel's stylish pool area, offering a serene retreat with loungers.
P7,635
P8,505 total
includes taxes & fees
Oct 6 - Oct 7
Tholaria Boutique Hotel
A pool with clear blue water, surrounded by lounge chairs and umbrellas, overlooking a rocky coastline.
A balcony with a view of the sea and a distant boat.
A coastal building with multiple balconies, a rocky shoreline, and a clear view of the sea.
A living room with a sofa, a coffee table, a vase, and a staircase.

2. Caldera Studios

Caldera Studios
Astypalaia
  • Seaside guesthouse offers pool, sun loungers, and umbrellas mere steps from the beach.
P2,313
P2,569 total
includes taxes & fees
Nov 4 - Nov 5
Caldera Studios
A table with two glasses of wine, a bottle of champagne, and a charcuterie board with various cheeses, meats, and crackers. In the background, there is a pool and a building with lights on.
A clear turquoise sea with rocky cliffs and a prominent rock formation in the center.
A multi-story building with stone facades, balconies, and a staircase leading to an upper level.
A breakfast table with various foods and drinks, overlooking a scenic ocean view.

3. GrandeMar Suites

GrandeMar Suites
Astypalaia
P23,859
P26,277 total
includes taxes & fees
Oct 6 - Oct 7
GrandeMar Suites
A pool area with a view of the sea and hills, surrounded by lounge chairs and umbrellas.
A white building with blue shutters and a stone staircase.
A bedroom with a bed, a bathroom with a blue door, and a view of the sea.
A rooftop terrace with seating and a view of the sea.

4. Castellano Village

Castellano Village
Astypalaia
P5,408
P6,276 total
includes taxes & fees
Oct 17 - Oct 18
Castellano Village
A modern outdoor pool area with a view of a distant island and sea.
A room with a wooden staircase, a small table, and a door leading to another room.
A wicker chair with a view of a blue and white tiled floor, a rock, and a potted plant.
A bedroom with a wooden ceiling, a bed with a patterned bedspread, a bedside table, a wall-mounted TV, and a small shelf with decorative items.

5. Siesta Villas, Cycladic Elegance With Castle View

Siesta Villas, Cycladic Elegance With Castle View
Astypalaia
  • Castle-view Cycladic residence features outdoor pool, private yard retreats, and garden serenity.
P10,951
P12,137 total
includes taxes & fees
Oct 7 - Oct 8
Siesta Villas, Cycladic Elegance With Castle View
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Choose what matters most at hotels with a pool in Astypalaia

Breakfast included
4 stars
5 stars
Hot tub
Spa

Hotels with pools and free breakfast in Astypalaia

A pool area with a view of the sea, white furniture, and a small table with flowers.
A balcony with a view of the sea and hills.
A bedroom with a bed, a TV, a sofa, and a view of the sea.
A coastal view through a window with a view of the sea and rocky terrain.

Tholaria Boutique Hotel

Tholaria Boutique Hotel
Astypalaia
P7,635
P8,505 total
includes taxes & fees
Oct 6 - Oct 7
Tholaria Boutique Hotel
A clear blue pool with white walls and a view of the sea. There are lounge chairs and a small table.
A modern bathroom with a central wooden partition, multiple sinks, and mirrors.
A long wooden table with various food items and glassware, set in a bright kitchen with white cabinets and a clock on the wall.
A modern hotel room with a glass staircase, a bed with a yellow accent, and a cart with toiletries.

Pylaia Boutique Hotel & Spa

Pylaia Boutique Hotel & Spa
Astypalaia
Pylaia Boutique Hotel & Spa
A pool with clear blue water, surrounded by lounge chairs and umbrellas, overlooking a rocky coastline.
A living room with a sofa, a coffee table, a vase, and a staircase.
A coastal building with multiple balconies, a rocky shoreline, and a clear view of the sea.
A neatly made bed with a wooden box labeled "HOME" on top, a bottle of honey, and a welcome mat with a "welcome" sign.

Caldera Studios

Caldera Studios
Astypalaia
P2,313
P2,569 total
includes taxes & fees
Nov 4 - Nov 5
Caldera Studios
A clear turquoise sea with rocky cliffs and a prominent rock formation in the center.
A table with two glasses of wine, a bottle of champagne, and a charcuterie board with various cheeses, meats, and crackers. In the background, there is a pool and a building with lights on.
A multi-story building with stone facades, balconies, and a staircase leading to an upper level.
A breakfast table with various foods and drinks, overlooking a scenic ocean view.

GrandeMar Suites

GrandeMar Suites
Astypalaia
P23,859
P26,277 total
includes taxes & fees
Oct 6 - Oct 7
GrandeMar Suites
A pool area with a view of the sea and hills, surrounded by lounge chairs and umbrellas.
A white building with blue shutters and a stone staircase.
A bedroom with a bed, a bathroom with a blue door, and a view of the sea.
A rooftop terrace with seating and a view of the sea.

Castellano Village

Castellano Village
Astypalaia
P5,408
P6,276 total
includes taxes & fees
Oct 17 - Oct 18
Castellano Village
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 3 weeks ago
Castellano Village
Pylaia Boutique Hotel & Spa

Pylaia Boutique Hotel & Spa

8/10 Good
"Very nice Hotel the staff was amazing. The Hotel was clean and modern most of the rooms have ocean views. The only area of improvement I would be for the gym to have Wi-Fi and air-conditioning and more weights and equipment."
REGINEL 5-night trip
Posted 1 month ago
Pylaia Boutique Hotel & Spa
Tholaria Boutique Hotel

Tholaria Boutique Hotel

10/10 Excellent
"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."
Angelo 3-night trip
Posted 3 months ago
Tholaria Boutique Hotel

Frequently asked questions

What are some accommodations with pools in Astypalaia?
Kallichoron Art Hotel: Provides a full-service spa, an outdoor pool, and a snack bar/deli. Chrysalis Boutique Hotel: Features a snack bar/deli, an outdoor pool, and free self parking. Pylaia Boutique Hotel & Spa: Offers free self parking, an outdoor pool, and complimentary wireless internet access. Caldera Studios: Features spa services, an outdoor pool, and buffet. Aphrodite Studios: Offers complimentary wireless internet access, a pool, and kitchens.
What is there to see and do in Astypalaia?
Make a point to visit attractions like Astipaleas Beach and Livadi Beach. Discover sights such as Astypalea Windmills, Astypalaia Castle, and Central Square during your stay. Take in the natural beauty of Astypalaia with the island views.
When is the best time to book a hotel with a pool in Astypalaia?
You may want to think about a place to stay that has an outdoor pool if you plan to visit Astypalaia in the hottest months of August, July, or September when the average temp is 77°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or March when the average temperature is 57°F.