Cyclades Islands Vacation Rentals from CA $37: Short-Term Rentals for 2026

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Our top choices for Cyclades Islands vacation rentals

A swimming pool with a view of the sea and buildings in the background.

1. family love suites

Santorini

Eilidh

CA $65 total

includes taxes & fees

Nov 28 - Nov 29

A pool area with a clear view of the ocean, a white building with arches, and a palm tree.

2. MyLifeSuites

Fira

Kimberley

CA $43 total

includes taxes & fees

Nov 20 - Nov 21

A hot tub with a view of the sea and a dome structure.

3. Lava suites

Fira

Todd

CA $133 total

includes taxes & fees

Nov 24 - Nov 25

A covered outdoor patio with a table and chairs, a bottle of wine, and a view of the beach and ocean.

4. Aegean Nest Beach Studios - Adults Only

Santorini

socheata

CA $77 total

includes taxes & fees

Nov 15 - Nov 16

A narrow street with white buildings, a tree with pink flowers, and a cobblestone path.

5. Melinas House - Mykonos Town

Mykonos

Blake

CA $77 total

includes taxes & fees

Nov 17 - Nov 18

A bedroom with a bed, a bedside table, a mirror, and a hanging light fixture.

6. Cavora Suites

Santorini

CA $71 total

includes taxes & fees

Nov 15 - Nov 16

A coastal terrace with a wooden table and chairs, a woven umbrella, and a view of the sea and a rocky outcrop.

7. Portara Seaside Luxury Suites

Old Town Naxos

Emory

CA $136 total

includes taxes & fees

Nov 15 - Nov 16

A modern building with a white facade, a wooden bench, and potted plants.

8. Anemelia way of living

Naousa

Sacha Maria

CA $155 total

includes taxes & fees

Nov 15 - Nov 16

A spa area with a hot tub, a glass of red wine, and a tray of fruits.

9. Black Rock villas

Santorini

daniel

CA $86 total

includes taxes & fees

Dec 15 - Dec 16

A rooftop swimming pool with a view of the city skyline and a flag.

10. Casa Grande Santorini

Megalochori

Steven

An aerial view of a hotel with three hot tubs, outdoor seating, and a tree.

11. Yiota Collection 4 Suites & 4 Prive Jacuzzi

Santorini

rommel

CA $127 total

includes taxes & fees

Nov 15 - Nov 16

An outdoor dining area with a view of the sea, a hanging chair, and a stone wall.

12. Seacode Villas

Mykonos

Maykol

CA $160 total

includes taxes & fees

Nov 27 - Nov 28

A hotel room with a bed, a window with curtains, a small table with a decorative item, and a view of the outdoors.

13. Ebita's Suites

Karterádos

Kjersti

CA $60 total

includes taxes & fees

Nov 22 - Nov 23

A rooftop pool with clear blue water, surrounded by white lounge chairs and a metal ladder.

14. Summer Time

Santorini

Victoria

CA $92 total

includes taxes & fees

Nov 22 - Nov 23

An arched doorway leading to a balcony with a view of a coastal landscape.

15. Althea suites

Paros

CA $210 total

includes taxes & fees

Dec 1 - Dec 2

A terrace with a pool, two chairs, a table with breakfast, and a view of the sea and city.

16. Lackos Luxury Suites

Santorini

Ryan

CA $131 total

includes taxes & fees

Dec 5 - Dec 6

A wooden deck with two lounge chairs and a small table, overlooking a coastal view with clear blue waters and distant landforms.

17. Santo Blue Santorini

Santorini

Syed

CA $137 total

includes taxes & fees

Nov 16 - Nov 17

A luxurious outdoor area with a hot tub, seating, and a view of a coastal town at night.

18. The A Collection, Oia by K&K

Santorini

JOSEPH

CA $246 total

includes taxes & fees

Nov 15 - Nov 16

A bathtub with a view of a body of water and a distant landmass.

19. Nano Oia Villas

Santorini

Danner

CA $156 total

includes taxes & fees

Nov 15 - Nov 16

A modern interior with a sofa, a coffee table, and a TV mounted on the wall.

20. Black Lithos Residences

Santorini

CA $157 total

includes taxes & fees

Nov 15 - Nov 16

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Find vacation rentals that suit your style

Top Cyclades Islands Hotel Reviews

A rooftop pool with white lounge chairs and a view of the sea.

Eden View Suites & Villas

Mykonos

10/10 Excellent

Hammad

A terrace with a table and chairs overlooking a blue sea and distant land.

Absolute Bliss

Santorini

10/10 Excellent

Amazing property with spectacular views of the caldera! They were very easy to communicate with before and throughout the stay! I got a surprise complimentary upgrade to a superior room with a spacious outdoor balcony that has unobstructed views of the caldera with beautiful sunsets, and a hot tub! A complimentary welcome bottle of local red wine topped it off - what a way to enjoy the sunset in your own hotel room! Daily freshly made breakfast served to your room was nice! The property has...

Chia Wei

A seaside view with white buildings and blue domes, overlooking the sea.

Oia Spirit Studios by Mary D Nomikou

Santorini

10/10 Excellent

Guo

An open doorway leading to a balcony with a view of the sea and rocky landscape.

Spitia Santorini

Santorini

10/10 Excellent

The room itself was beautiful and the location couldn’t be beat! Beautiful views. Loved the uniqueness of the cave room. Only thing to note was the placement of the shower… kind of ran over a seat in the shower, which made it difficult to stand underneath. Also, the ‘hot tub’ was definitely not hot lol. More of a warm bath, depending on the weather that day. Was definitely too cold to go in during the evening.

Sydney

A poolside area with white lounge chairs and a small umbrella, set against a white building with multiple windows and doors.

Winery Hotel 1870

Santorini

10/10 Excellent

Kyla

A pool area with a clear view of the sea and islands in the background.

Dreams Luxury Suites

Santorini

10/10 Excellent

Anonymous traveller

A pathway leading to a white building with a door, surrounded by stone walls and palm trees.

Milena Hotel

Mykonos

10/10 Excellent

Josie

Divino Caldera

Santorini

10/10 Excellent

The property is great. The rooms , the pools, the views, everything is perfect expect breakfast. You have to wait for it for half or even hour. If you are not in a rush it is ok but if you have plans, it is inappropriate. The restaurant itself is expensive . But if you go just about 10 min up you have choice of three taverns with a beautiful views of sunset. Keep in mind if you want to go to Fira or Oia it takes about 25-30 min by car.

Liudmila

A hot tub in a well-lit outdoor area with wooden deck, lounge chairs, and potted plants.

Vincenzo Family Hotel

Tinos

10/10 Excellent

Nancy

Find out more about Cyclades Islands

Everything you need to know about Cyclades Islands vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cyclades Islands vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cyclades Islands vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cyclades Islands vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cyclades Islands. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cyclades Islands vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cyclades Islands vacation rentals we have selected for you start as low as CA $37 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cyclades Islands rentals

At Expedia, we put the best Cyclades Islands vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cyclades Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cyclades Islands vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cyclades Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Aegean Islands Vacations
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Cyclades Islands Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cyclades Islands vacation rentals

1. family love suites

2. MyLifeSuites

3. Lava suites

4. Aegean Nest Beach Studios - Adults Only

5. Melinas House - Mykonos Town

6. Cavora Suites

7. Portara Seaside Luxury Suites

8. Anemelia way of living

9. Black Rock villas

10. Casa Grande Santorini

11. Yiota Collection 4 Suites & 4 Prive Jacuzzi

12. Seacode Villas

13. Ebita's Suites

14. Summer Time

15. Althea suites

16. Lackos Luxury Suites

17. Santo Blue Santorini

18. The A Collection, Oia by K&K

19. Nano Oia Villas

20. Black Lithos Residences

Find vacation rentals that suit your style

Top Cyclades Islands Hotel Reviews

Eden View Suites & Villas

10/10 Excellent

Find out more about Cyclades Islands

Cyclades Islands vacation rentals: An excellent choice for every season

How to find incredible deals on Cyclades Islands rentals

Explore a world of travel with Expedia