Cyclades Islands Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Cyclades Islands vacation rentals

Cave Traditional Villa, Jetted Tub, Sea View | Private spa tub
Nano Oia Villas

Nano Oia Villas

Nano Oia Villas
Santorini
9.8 out of 10, Exceptional, (51)
"Our location had a beautiful view. It was centrally located to everything. "
United States
Cristo
$137 nightly
The price is $156
Jan 27 - Jan 28, 2026
Total with taxes and fees
Nano Oia Villas
Grand Suite, Sea View (Plunge Pool, Caldera View) | Terrace/patio
Aqua Luxury Suites

Aqua Luxury Suites

Aqua Luxury Suites
5.0 star property
Santorini
9.2 out of 10, Wonderful, (214)
"The view, price, food and service are all perfect! The only small thing that may make it better is to have a better hair dryer (Dyson or something similar but cheaper like Laifen or Dreame). I really love the days staying in the hotel"
Canada
Tino
$208 nightly
The price is $236
Dec 30 - Dec 31
Total with taxes and fees
Aqua Luxury Suites
Exterior
Seacode Villas

Seacode Villas

Seacode Villas
Mykonos
10.0 out of 10, Exceptional, (17)
"Beautiful property with amazing views, private pool, hot tub, onsite parking and walkable to beach. This was an amazing 3 bedroom property with amazing views of the sea and beach. Pool, outdoor kitchen and hot tub were very nice. "
United States
Perianan
$112 nightly
The price is $128
Jan 15 - Jan 16, 2026
Total with taxes and fees
Seacode Villas
Villa, 2 Bedrooms (Thetis Cave Villa) | Living area | Flat-screen TV
Thetis Cave Houses

Thetis Cave Houses

Thetis Cave Houses
Santorini
9.6 out of 10, Exceptional, (32)
"Timis met us there at 9 pm for checkin. this place is very clean and very unique. Right in the heart where all the shopping and scenery is. We loved it!"
Canada
John
$136 nightly
The price is $155
Dec 30 - Dec 31
Total with taxes and fees
Thetis Cave Houses
Deluxe Room, 1 Queen Bed | In-room safe, soundproofing, iron/ironing board, cribs/infant beds
AK Mykonos

AK Mykonos

AK Mykonos
Mykonos
9.8 out of 10, Exceptional, (62)
"Great location, friendly staff, very clean, great value."
United States
Liv
$89 nightly
The price is $102
Jan 11 - Jan 12, 2026
Total with taxes and fees
AK Mykonos
Outdoor pool, sun loungers
Nefeles Luxury Suites

Nefeles Luxury Suites

Nefeles Luxury Suites
Santorini
9.6 out of 10, Exceptional, (164)
"Panos the manager was amazing & very attentive. The view was amazing & breakfast was delicious. "
United States
Sydney
$201 nightly
The price is $229
Jan 11 - Jan 12, 2026
Total with taxes and fees
Nefeles Luxury Suites
Superior Suite, Private Pool, Sea View (Amalthia) | Terrace/patio
Amallini Suites Mykonos

Amallini Suites Mykonos

Amallini Suites Mykonos
Mykonos
10.0 out of 10, Exceptional, (10)
"Amazing"
United States
Yazael
$231 nightly
The price is $251
Jan 1 - Jan 2, 2026
Total with taxes and fees
Amallini Suites Mykonos
Outdoor spa tub
Andros 4 All Seasons Villas & Suites

Andros 4 All Seasons Villas & Suites

Andros 4 All Seasons Villas & Suites
Andros
9.6 out of 10, Exceptional, (4)
"Our stay was nothing short of spectacular. This hotel was marvelous & beyond my expectations in terms of cleanliness & service. The location was also fantastic & within walking distance of the beaches & restaurants in Korthi. I highly recommend this hotel for anyone looking for a wonderful place to stay while in Andros."
United States
Anonymous traveler
$192 nightly
The price is $219
Jan 7 - Jan 8, 2026
Total with taxes and fees
Andros 4 All Seasons Villas & Suites
Outdoor pool, pool umbrellas, sun loungers
Tinos Resort Hotel

Tinos Resort Hotel

Tinos Resort Hotel
4.0 star property
Tinos
9.4 out of 10, Exceptional, (32)
"The owner of this property was extremely friendly, very knowledgable of the area and the room was very clean and the staff that worked there were wonderful! If you’re looking for a true traditional Greek experience, this is the place to stay."
Canada
Georgina
Tinos Resort Hotel
Avax Villa by K&K | Premium bedding, individually decorated, iron/ironing board, free WiFi
The A Collection, Oia by K&K

The A Collection, Oia by K&K

The A Collection, Oia by K&K
Santorini
9.4 out of 10, Exceptional, (19)
"Very clean & beautiful cave home. Everything that we needed was provided to us. "
United States
Kailee
$140 nightly
The price is $164
Jan 6 - Jan 7, 2026
Total with taxes and fees
The A Collection, Oia by K&K
Front of property - evening/night
Portiani Suites

Portiani Suites

Portiani Suites
Milos
9.6 out of 10, Exceptional, (25)
"Great hotel location and friendly staff. "
United States
Nayeli
$104 nightly
The price is $119
Jan 6 - Jan 7, 2026
Total with taxes and fees
Portiani Suites
Comfort Room, Pool View | View from room
The Noverian Bios Santorini

The Noverian Bios Santorini

The Noverian Bios Santorini
Santorini
9.2 out of 10, Wonderful, (9)
"Seriously have nothing but amazing things to say about our stay here!! The room was perfect and very clean. There was free water, slippers, and coffee each day for us. Helena was so attentive and kind - making sure everything was perfect each day + giving so many options for beach clubs and excursions in Santorini. The location was very walkable and close to the bus station + downtown Fira. Breakfast delivered to the room was such a treat. I would recommend this hotel to absolutely anyone...
United States
Maraci
$56 nightly
The price is $66
Jan 24 - Jan 25, 2026
Total with taxes and fees
The Noverian Bios Santorini
Front of property
Aloft Suites Mykonos Island

Aloft Suites Mykonos Island

Aloft Suites Mykonos Island
Mykonos
$191 nightly
The price is $218
Jan 27 - Jan 28, 2026
Total with taxes and fees
Aloft Suites Mykonos Island
Exterior
Black Rock villas

Black Rock villas

Black Rock villas
Santorini
9.2 out of 10, Wonderful, (19)
"We stayed here during the off-season and enjoyed tiptop rates and a very nice place to sleep. Safe and comfortable and modern and a great host with lots of local information."
United States
Michael
$53 nightly
The price is $61
Jan 7 - Jan 8, 2026
Total with taxes and fees
Black Rock villas
Terrace/patio
Afoura Houses by K&K

Afoura Houses by K&K

Afoura Houses by K&K
Santorini
9.0 out of 10, Wonderful, (54)
"Clean and spacious room in a quiet location. They forgot to send the check in instructions so it was difficult to find the room."
United Kingdom
Francesco
Afoura Houses by K&K
Exterior
Alma Syros

Alma Syros

Alma Syros
Syros
10.0 out of 10, Exceptional, (14)
"Beautiful hotel in a convenient central location in Syros. Very friendly and helpful staff. Great facilities and felt extra special and comfortable for my entire stay."
United States
Vanessa
$79 nightly
The price is $91
Jan 7 - Jan 8, 2026
Total with taxes and fees
Alma Syros
Apartment, Smoking | 2 bedrooms, desk
Stella's Loft In Center Of Tinos

Stella's Loft In Center Of Tinos

Stella's Loft In Center Of Tinos
Tinos
$98 nightly
The price is $112
Jan 3 - Jan 4, 2026
Total with taxes and fees
Stella's Loft In Center Of Tinos
Exterior
Oia Mansion

Oia Mansion

Oia Mansion
Santorini
9.8 out of 10, Exceptional, (8)
"This place was amazing! Beautiful property and Lily and her family were amazing hosts! The breakfast every morning was perfect and everyone was helpful and friendly. Highly recommend this property! "
United States
Melissa
$664 nightly
The price is $759
Jan 12 - Jan 13, 2026
Total with taxes and fees
Oia Mansion
Property grounds
NINEMIAN SUITES SYROS

NINEMIAN SUITES SYROS

NINEMIAN SUITES SYROS
Syros
10.0 out of 10, Exceptional, (1)
"The place is in a wonderful location and it’s a beautiful apartment. There was a small lack of communication at first arrival but it was quickly solved."
United States
Trenton
$126 nightly
The price is $143
Jan 10 - Jan 11, 2026
Total with taxes and fees
NINEMIAN SUITES SYROS
Elite Villa, 2 Bedrooms, Hot Tub, Sea View | Terrace/patio
Three Domes Oia - an Iconic Collection

Three Domes Oia - an Iconic Collection

Three Domes Oia - an Iconic Collection
Oía
9.4 out of 10, Exceptional, (14)
"Beautiful views great pool and location "
United States
Naisi
$181 nightly
The price is $207
Jan 1 - Jan 2, 2026
Total with taxes and fees
Three Domes Oia - an Iconic Collection
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 Cyclades Islands Hotel Reviews

Athina Luxury Suites

Athina Luxury Suites

10/10 Excellent
"Food, specially the daily breakfast "
Nestor 3-night trip
Posted 9 days ago
Athina Luxury Suites

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Cyclades Islands in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $66 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.